BY: CHRISTOPHER BROWN

 

Sometimes, you just need a quick escape. A change of scenery to recharge, explore, and break free from the daily routine.

 

The “Weekender” is a travel series that is your go-to guide for the perfect weekend getaway. Each article will spotlight a different destination, offering insider tips on where to stay, what to do, what to eat and drink, and how to make the most of your time so you can spend less time planning and more time enjoying your trip.

 

This weekend, we are taking you to Chicago, Illinois, the Windy City. This article will be in a slightly different format than usual. Instead of just giving you my recommendations, I’m bringing you along on my previous trip to Chicago.

 

My wife, Venus, and I wanted to change up the way that we typically celebrate the holidays, so we decided to leave town on New Year’s Eve and fly to Chicago to spend an extended weekend there. We had only been to Chicago once many years ago. During that trip, we were only there for a day, so we didn’t get to explore much of the city. This time, we wanted to take some time to see what the Windy City has to offer.

 

Chicago is the third largest city in the United States and is positioned right on Lake Michigan. It’s proximity to Lake Michigan makes the city susceptible to strong winds, giving Chicago the nickname, the Windy City. Some say it got the nickname because Chicago’s politicians were known to be boastful. Chicago has a fundamental and extensive history that is far too big to discuss in this already long article. The city has a population of 2.7 million residents, has the United States 2nd largest public transportation system, 24 lakefront beaches, 600 parks, 8 major league sports teams, 7,300 restaurants, 160 breweries, some of the world’s tallest buildings, and much more.

 

The first time we visited, we drove seven to eight hours to get to Chicago from West Virginia. Thirty minutes before we got to the city, I hit a pot-hole on the interstate and blew out a tire. It was raining and in the middle of rush hour, so putting the donut on my car was a nightmare. Half of our trip was taken up by trying to find someone to replace the tire so we wouldn’t have to drive back on a spare. To avoid the long drive and any potential mishaps, we decided to fly this time around.

 

Flight tickets were reasonably priced, costing about $400 for both of us round-trip. We decided not to rent a car for this trip. Parking in Chicago is extremely expensive, not to mention, that I hate the rental car process; picking up, dropping off, paperwork, liability, etc. Chicago’s public transit system is affordable and convenient for getting around the majority of the city. Walking is a necessity in Chicago. In the winter it can be extremely cold, so there were times during our trip when we chose to use Uber, Lyft, or take a taxi to get to some destinations just to avoid longer walks in the cold. Each ride averaged around $5-10.

 

Tuesday, December 31st

 

We flew out of Charleston, WV on December 31st at 7:30 am. Just over an hour later, we touched down in Chicago. We picked up our bags from baggage claim and headed straight for the “L”, Chicago’s public transport train system. The “L” is short for “elevated” because the train system runs mostly above ground and is elevated above the streets. We purchased a 3-day pass for $15.00 each, which would give us an unlimited number of rides. The train ride from the airport to the train station closest to our hotel took around 45 minutes.

 

We booked a stay at the Hyatt Place (Downtown Loop) because it was within the Loop and it was only one block away from a train station. The Loop is the center of downtown Chicago. It’s called the Loop because all of the “L” trains loop in a circle around this downtown area. After they make their loop, they split off to different areas of the city. Staying within the Downtown Loop makes it easy to get around and easy to figure out how to navigate the city using the “L”. Throughout this article, I’m going to provide the addresses and the nearest “L” stations for each destination mentioned.

 

When we arrived at the Hyatt, it was hours before our check-in time, but the hotel offered to hold our bags until then. We dropped off our bags and immediately hopped back on the “L” to go and get breakfast. After getting off the train, we walked a couple of blocks and made our first stop at “The Bean”.

 

The Bean/Cloud Gate – Millennium Park (“L” Orange & Red Line – Millennium Station)

 

 

The proper name for “The Bean” is “Cloud Gate”, but it’s better known as “The Bean” because it’s shaped like… a bean. Located in Millenium Park, the Bean is an iconic work of public art inspired by liquid mercury. It is constructed from 168 stainless steel plates that are perfectly polished, reflecting the Chicago skyline and the people around it. The Bean is one of Chicago’s most popular sights and a must-see when you visit.

 

Wildberry Pancakes & Cafe – 130 E Randolph St (“L” Orange & Red Line – Millennium Station)

 

 

A block away from the Bean, we had breakfast at Wildberry Pancakes & Cafe. Wildberry is one of the most popular spots to get breakfast in Chicago. This place is so popular that when we arrived, there was a 45-minute wait with a large crowd of people waiting outside. The bad part? It was cold and raining. We stood as close to the building as possible and waited in the rain until our table was ready. It was totally worth it. We ordered coffee, with both the Mexicana and Denver breakfast skillets. They’re known for their pancakes so we had both their banana cream pancakes and the “Berry Bliss” pancakes as our sides. The breakfast skillets are fantastic and the pancakes are some of the best that I’ve ever had. I liked them so much that I came home and tried to replicate them the next weekend (with slight success). If you come to Chicago and are looking for breakfast, go to Wildberry and you’ll leave impressed, even if you have to wait.

 

*Pro Tip* I didn’t know this until it was too late, but you can make reservations ahead of time on Yelp to avoid the wait.

 

After breakfast, it was only 11:30 am. We still had time to kill before we could check into our hotel, so we decided to visit the Navy Pier. The Navy Pier isn’t near a train station, so we had to take a 5-minute Uber ride to it.

 

Navy Pier (Uber/Lyft/Taxi)

 

 

The Navy Pier is a 33,000 ft long pier on Lake Michigan. It’s Chicago’s second-most-visited attraction, which has shops, restaurants, family attractions, parks, gardens, and more. At the top of the pier is a small amusement park featuring the iconic Navy Pier Wheel. The pier is also home to many events and seasonal festivals. It was New Year’s Eve, so the winter festivities were closed for the day.

 

We arrived at the pier and walked its entire length. Most of the pier is indoors and it is much bigger than it seems. There are so many restaurants, shops, and attractions that just when you think you’ve reached the end and there couldn’t possibly be more, you’re in a new section of the pier. When we finally reached the end of the pier, we walked outside to see Lake Michigan and the city skyline. If you’ve never seen one of the Great Lakes in person, the lakes look like an ocean. It was nearly snowing, freezing cold, and the wind made it five times worse, so we didn’t last long outside. Before we left, we went to the top of the pier to see the Navy Pier Wheel.

 

Afterward, it was only 1:30 pm and we still needed to waste some time before check-in. My favorite way to waste time in any city is at a brewery, so we took an Uber to Crushed By Giants Brewing Company.

 

Crushed By Giants Brewing Company – 600 N Michigan Ave 2nd Flood (“L” Red Line – Grand)

 

Crushed By Giants was the first brewery we visited in Chicago and by the end of the trip ended up being one of my favorites in the city. Crushed By Giants is located in the Downtown Loop and is in one of the weirdest locations for a brewery. It’s located on the second floor of a large building downtown and shares a space with an AMC movie theater. You have to take escalators up to the brewery but once you walk in, it’s surreal how you don’t feel like you’re in downtown Chicago. The taproom is cozy and feels like a brewery. Their aesthetic and beer artwork are awesome. They had food but we still weren’t hungry after breakfast, so we just had a couple of beers while we planned the rest of our day. Again their beers were some of the best I had during the entire trip, so if beer is your thing, I recommend you visit Crushed By Giants.

 

Our hotel gave us an early check-in, so we left Crushed by Giants and headed to the nearest “L” station and took it back to our hotel to check in, after which, we took a two-hour nap to get some energy before heading back out for New Year’s Eve.

 

Portillo’s & Barnelli’s – 100 W Ontario St (“L” Red Line – Grand)

 

After our much-needed nap, we were ready to hit the city again to bring in the New Year. We took the “L” to the closest Portillo’s, a Chicago food staple, serving Chicago-style hotdogs and Italian beef sandwiches (we’ll discuss those later). Chicago hotdogs are different. They’re beef hotdogs, served on poppy seed buns with mustard, relish, celery salt, onions, sliced tomatoes, a pickle spear, and roasted sweet peppers. We ordered one to share and ended up ordering a second one because it was so good that it was impossible to share just one. In Portillo’s, you order at a touch-screen, seat yourself, and walk up to get your order when it’s ready. The vibes in the restaurant are nostalgic, pre-prohibition-themed, and quirky.  If you want beer, they also have a separate beer bar that serves beers in large glass goblets, though I was still saving my liver for the next stop. When you visit Chicago, you have to have a Chicago-style hotdog and Portillo’s is the perfect place to get one.

 

After eating at Portillo’s, my wife still needed some more energy, so we walked across the street to the McDonald’s next to the Hard Rock Cafe to get her a coffee. While she drank her coffee, we took a 15-minute Uber ride north to the Ravenswood neighborhood. The “L” does go to Ravenswood, but it was getting late and we didn’t want to waste time walking to and waiting on the train.

 

 

Begyle Brewing –  1800 W Cuyler Ave (“L” Brown Line – Irving Park)

 

Our driver dropped us off at Dovetail Brewing (one of the breweries on my itinerary), but when we arrived, they had closed early for the holiday. Luckily, Begyle Brewing was one block away. Begyle Brewing is an Irish-themed brewery. When we arrived, they had recently finished celebrating the New Year in Ireland. We had a couple of beers and played board games until around 8:30 pm. Begyle Brewing was a happy accident for us. They have excellent beer and towards the end of the night gave all patrons free tasters of barrel-aged stouts. They had a food truck outside and according to their posted calendars, always seemed to have events happening. If I lived in Chicago, I’d be a regular to Begyle.

 

 

House Calls

 

 

I plan everything when I travel. So our final destination for the last day of the year was within walking distance. Our primary reason for coming to Chicago was to go to House Calls. House Calls is a company that hosts house music events every week. They host shows at their Listening Room or do pop-up events around the city. Each week features a different house music DJ. House music is the oldest genre of electronic music. It’s a steady four-to-the-floor beat at 115-130 bpm with a prominent kick drum, open and off-beat high-hats, with claps/snares. Add in a deep bassline or synthesizer, soulful vocals, and/or samples and you get house music. It’s a very chill dance music genre compared to EDM/dubstep.

 

My wife and I got into house music last year after discovering an artist named FredAgain…(go listen to him). House music shows don’t exist anywhere near our general area, so we planned our whole trip to Chicago around House Calls.

 

 

On New Year’s Eve, House Calls was held at a special venue in Ravenswood. We passed through security and went into the venue. We had paid for VIP tickets so we could have special access to a VIP bar and get stage access behind the DJ. We thought we were early, but the opening DJ had already started her set. The music volume is perfect. You can still talk to each other and hang out without having to scream into each other’s ear.

 

 

The venue itself was beautiful. The lights were low and cozy. We grabbed a drink and hung out all night, just talking, listening to music, and dancing. The vibes at these shows are different than those of most concerts. People genuinely just spend time hanging out, talking, and dancing. The main act Dennis Ferrer, a house music OG, took the stage an hour before midnight. We went up on the stage and danced into the New Year. After the show, I was able to meet and speak with Dennis. We left the venue and walked to the “L”, taking it back to our hotel for the night.

 

Wednesday, January 1st

 

After some much-needed rest, we woke up late at 11 am. Both of our bodies were sore from the night of dancing and we were slightly hungover. The perfect remedy? Food and coffee. We hopped on the “L” and took it to the Magnificent Mile. The Magnificent Mile is a shopping district in Chicago. There are restaurants, hotels, and designer stores, like Dior, Balenciaga, Saint Laurent, Louis Vuitton, and many more. It was a very cold day, so a hot bowl of ramen was sure to cure our hangovers and warm us up.

 

Ramen San – 165 E Huron St (“L” Red Line – Chicago)

 

Ramen San is a Japanese ramen restaurant. Japanese ramen is my favorite Asian soup. If you haven’t had it, you’re truly missing out. My favorite kind is tonkatsu, consisting of ramen noodles in a rich and usually creamy pork broth topped with a medium-boiled egg, scallions, enoki mushrooms, and pork belly. We both ordered their “10-hour tonkatsu” lunch special. I had a Japanese beer, Asahi. It’s rare to find Asahi on draft, so when I do,  I never pass on the opportunity. After our bellies were warm and content, we walked to the Starbucks Reserve Roastery.

 

Starbucks Reserve Roastery – 646 Michigan Ave (“L” Red Line – Grand)

 

The Starbucks Reserve Roastery in Chicago is the largest Starbucks in the world. This obviously isn’t the average Starbucks. There are only six Starbucks Reserve Roasteries in the world. All of them are built to be upscale and provide immersive coffee experiences. When we arrived there was a long line outside of the door, even in the cold weather. Luckily, we arrived at the right time and got in pretty quickly. The Roastery has four floors, each featuring something unique. The first floor is the Main Reserve coffee bar where you can get coffee and food to-go. The second floor is a bakery and cafe. The third floor is an experimental floor, where they serve special and unique coffees and drinks that are reserved only for the Roastery. The top floor is a cocktail bar where they serve cocktails, wine, beer, and their signature espresso martinis.

 

We had a Toffenut Bianco Latte and a spirit-free whiskey barrel-aged cold brew coffee from the experimental floor. Before leaving, I had to try an espresso martini from Starbucks, so we went up to the fourth-floor cocktail bar. They make many flavors of espresso martinis and even serve flights of them for those who want to try them all. I just ordered the original espresso martini and it was easily the best espresso martini I’ve ever had in my life. All of the coffee from the Roastery was phenomenal. I gained a newfound respect for Starbucks that day. The barrel-aged cold brew coffee absolutely blew my mind. I still think about it often. If you’re a coffee or Starbucks lover, the Starbucks Reserve Roastery is a one-of-a-kind experience.

 

After we had our coffee, we window-shopped in the Magnificent Mile for a bit before taking the “L” back up to the Ravenswood neighborhood to visit the brewery that was closed the night before.

 

Dovetail Brewery – 1800 W Belle Plaine Ave (“L” Brown Line – Irving Park)

 

We had to come back here when they were open because Dovetail was at the top of the list of breweries to visit in Chicago. Dovetail specializes in European styles using traditional methods. The brewers here attended brewing school in Munich, Germany, and returned to Chicago to open Dovetail Brewery. In my humble opinion, German beer is the best of the best and these guys certainly brought those skills back with them. They use all European imported ingredients, historic water profiles, and other traditional methods like decoction mashing and open fermentation.  I’m glad that we made the trip back because this was easily the best beer that I had in Chicago. My favorites were the Kölsch (served properly in a strange) and their Festbier. No fancy names are needed here, just damn good beer.

 

It was time for dinner and Oregon was playing Ohio State in the college football semi-final. I wanted to watch the game while having my favorite comfort food, buffalo wings, so we went to a nearby sports pub to watch the game.

 

Jake Melnick’s Corner Tap – 41 E Superior St (“L” Red Line – Chicago)

 

Jake Melnick’s is known as one of the best sports bars in Chicago. They serve the pub classics; like wings, burgers, and beer. It was exactly what I was craving at the time. I don’t have much to say other than if you want to watch sports and/or have some good pub food, this place hits the spot.

 

After dinner, Venus was still exhausted from NYE, so we took the “L” back to the hotel. She wanted to sleep but I was still full of energy from the Starbucks cold brew. The night was still young, so I ventured back out and took the “L” to Guinness Open Gate Brewery.

 

Guinness Open Gate Brewery – 901 W Kenzie St – (“L” Blue Line – Grand)

 

When you hear “Guinness” you probably think about a jet-black beer from Dublin, Ireland. While their iconic Irish stout is brewed in Ireland, Guinness is also a brewery that has multiple locations worldwide. Chicago is one city that is lucky enough to have a Guinness Brewery. Having a pint of Guinness in Dublin is on my bucket list, and since I haven’t been able to go to Dublin yet, going to the Guinness Brewery was the next best thing.

 

Surprisingly, when I was there, I didn’t order a stout. They had crispy yellow beers on the menu that I never thought Guinness would make. I sampled their menu trying beers like pale ales, cream ales, and light lagers. These are very rare styles for the Guinness brand and their cream ale is one of the best of the style that I’ve ever had. If beer isn’t your thing, they also have a full bar with both cocktails and mocktails, as well as, coffee. I was still full from dinner at Jake Melnick’s, so I didn’t try their food, but they have a full menu with something for everyone on it.

 

After I left Guinness, I took the “L” back to the Downtown Loop. By this time, the Guinness beers were kicking in, so I was ready to keep the night going. It was still New Year’s Day in Chicago, so most breweries were closed for the day. Instead, I found a small dive bar called Rossi’s Liquors.

 

Rossi’s Liquors – 412 N State St (“L” Red Line – Grand)

 

Aside from their name, Rossi’s serves more than liquor. I found this spot by asking Reddit for some good places to get craft beer. Even though it’s well-known, Rossi’s has a hole-in-a-wall vibe. It’s relatively small, cozy, and delightfully tacky. It’s a cash-only venue but they have an ATM on-site for those who come unprepared, like I did. I got a $20 bill out of the ATM and headed to the beer coolers. They have an extensive list of both local and non-local craft beers. Instead of ordering from the bartender, you grab the cans you want from the coolers and take them to the bartender so they can add it to your tab and serve it in a glass for you. I grabbed some local Chicago beers from breweries that I knew I didn’t have time to visit during this trip and sat at the bar. The bartender was a nice older lady who spoke to me like she’d known me her entire life. I felt like I was a regular. All of the other patrons were very nice, including a guy who had just legally immigrated from Mexico to Chicago and another couple from Chicago.

 

After a couple of drinks, I was ready to head back home for the night. When I walked out of Rossi’s, I wasn’t sure which way to go to get to the “L” station. A guy outside of the bar saw me looking at the maps on my phone and offered help. He said he was heading in the same direction and as we were walking, we walked past another bar. He asked if I wanted another drink and said that he was buying. At this point, my plans to get back to the warm hotel bed spiraled out of control. For the rest of the night, I walked around downtown Chicago and bar-hopped with people I’d just met at each venue. I didn’t make it back to the hotel room until 4 am. Spoiler alert: huge regrets.

 

Thursday, January 2nd

 

I woke up at 2 pm. Hungover… again. I had slept half of the day away. I had side-quested way too hard. Venus had already left the hotel room. I instantly called her to see where she had gone. She had gone back to the Magnificent Mile and was trying on a new pair of Uggs when she answered. Rightfully, she was a bit upset with me. I rushed to get dressed and took the “L” to meet her there as quickly as possible. After buying her a new pair of Uggs and explaining to her where I had been all night, all was well and our Chicago adventures continued.

 

Chinatown – (“L” Red Line – Cermak-Chinatown)

 

 

It was 3 pm and both of us were starving. Before my side-questing disintegrated our plans for the day, we had originally planned on going to Chinatown to have a Chinese breakfast, called dim sum. Luckily for me, the dim sum restaurant we had our eye on was still open. To avoid losing any more time, we took an Uber straight to Chinatown. Venus is Chinese-Vietnamese, so any time we travel to a city, we like to see what Asian options it has to offer. Chicago is one of those cities that has a dedicated Chinatown. Chicago’s Chinatown features a gateway/arch that marks the entrance of the Chinatown community. Inside Chinatown, you’ll find shops, restaurants, churches, bakeries, and more. As well as statues, pagodas, and murals, like the 9 Dragon Wall in Chicago. Chinatown is themed and decorated with red colors and Chinese symbols all around. It truly feels like you’ve entered a portal to China when you’re there. This part of the city is busy, even in the cold weather. People from all cultures are there to shop and have authentic Chinese cuisine. Before we could explore Chinatown, we needed to have some food.

 

Minghin Cuisine – 2168 S Archer Ave (“L” Red Line – Cermak-Chinatown)

 

Back to the dim sum. Surprisingly, this is the first time that I’ve written about dim sum. It’s one of our favorite things to eat when we travel to other cities. “Dim sum” itself translates to “touch the heart” and that’s exactly what it does for us. It is a type of Chinese brunch, consisting of small and steamed Chinese dishes like dumplings, bao buns, and more. Some restaurants offer cart service, where the servers push carts around to your table for you to take different dishes to eat. Minghin Cuisine doesn’t offer a cart service, but we already knew what kind of dim sum we wanted. First, we ordered hot tea. This is a must at a dim sum restaurant. Then we ordered shrimp and pork dumplings (shumai), shrimp dumplings (har gow), soup dumplings (xiao long bao), steamed rice paper with filling (Cheung fun), BBQ pork buns (char siu bao), and Venus’s favorite, BBQ chicken feet. I don’t like the chicken feet.

 

The flavor is great, but there are too many bones in them and I’m not built for navigating that many bones in each bite. I also know that it sounds like we ordered too much food, but each dim sum dish comes with only 3 or 4 items. Most dim sum dishes are supposed to be dipped in a mixture of soy sauce, malt vinegar, and chili sauce.  If you’ve never been to a dim sum restaurant, the next time you’re looking for brunch in another city that has dim sum, you should try it. It may be intimidating at first, but I think you’ll find that dim sum really does touch the heart. Remember.. embrace the unfamiliar.

 

After our bellies were full, we were ready to go explore Chinatown. We walked up and down every street, looking at all of the different Chinese restaurant options, browsing the different shops, and visiting a couple of Chinese bakeries to buy special pastries like mochi donuts and moon cakes. After we had seen all of Chinatown, he took the “L” north to Goose Island Brewing Co.

 

Goose Island Brewing Co. – 1800 W Fulton St (Uber/Lyft/Taxi)

 

I was still hungover and wasn’t in much of a mood to drink. Goose Island was on my list to visit while in Chicago, so I gave it my best college try. Goose Island is probably the most popular brewery out of Chicago. It’s the oldest currently operating brewery in the city and has been open since 1988. They’re now owned by Anheuser-Busch and distribute their beers across the USA. You’ve probably heard of Goose Island’s 312 Wheat Ale or their IPA. Though I wasn’t in much of a mood to drink, I had small tasters of the rare beers that they don’t distribute, like the Sofie Belgian-style saison and Full Pocket pilsner, and was fully impressed. We visited their taproom location, which doesn’t have a kitchen, so if you want food, go to their “Salt Shed Pub” location.

 

After leaving Goose Island, we were hungry again. I was craving another Chicago-style hotdog but Venus wasn’t feeling hotdogs. She wanted to try fufu, an African dish, so we decided to take the “L” around the city picking up food to-go for each of us to take back to our hotel. I found a random spot called Jimmy’s Gyros & Grill to get a Chicago hotdog and an Italian beef sandwich (more about this sandwich later).

 

We got off of the “L” long enough to pick up my food and got right back on to go to the South Side to an African restaurant called Yassa African Restaurant. Venus ordered goat curry with fufu. Fufu (translated to “mash”) is an African dish that is made of cassava or yams that are pounded until they form into what resembles a ball of dough. You take a small piece of the dough and dip it in your curry or soup. It’s supposed to be eaten and swallowed without chewing. We took the “L” back to the hotel room and ate our food in bed while watching the new season of Dexter: New Blood on Showtime. I tried her goat curry with fufu. Fufu is like a super starchy and sticky mashed potatoes. Combined with the curry it was super tasty, flavorful, and very rich. My Chicago-style hotdog and Italian beef hit the spot too. Shortly after eating our food, we both fell asleep.

 

January 3rd

 

It was our last full day in Chicago. We had a lot planned for the day, so we woke up early to get started. The day before, I had booked a Chicago architecture boat tour that was scheduled to depart at 10 am, but first? Coffee. We took the “L” to the Chicago Riverwalk area and stopped at Mojo Coffee to grab a quick coffee and croissant to-go. The Chicago Riverwalk is a walkable area located along the Chicago River. It features many restaurants, bars, cafes, small parks, tours, and more. During the summer, this area is bustling with people and many outdoor activities. It was 10 am and 19 degrees outside, so it wasn’t so busy when we were there.

 

Riverwalk Architecture Boat Tour – Chicago Riverwalk (“L” Orange & Red Lines – Millennium Station)

 

 

There are many companies that you can book a boat tour with. We booked our tour through “Get Your Guide”, which is a convenient app that has many activities that you can book in the city or area you’re traveling to. It works very similar to Airbnb but is for activities and experiences only. Get Your Guide hooked us up with Wendella Boat Tours. We found our way to the dock. They scanned our tickets and let us onto the tour boat, which was a double-decker boat featuring a full bar/cafe with both indoor and outdoor seating. We took a seat on the top deck before the tour started. From the beginning, our tour guide made the entire tour very interesting. At first thought, most wouldn’t think that architecture is very interesting but we were pleasantly surprised by how interesting and fun the tour was.

 

The tour boat travels along the Chicago River while the tour guide tells you all about Chicago’s 130-year-long history and its legendary architecture. Featuring buildings like the Trump Tower, the Wrigley Building, and the John Hancock Building (more on that later). The tour goes all the way to Lake Michigan and turns around. It was a cold and windy 19 degrees outside, so about halfway through the tour, we went to the inside cabin of the boat to warm up. I learned a lot about Chicago and architecture during this tour. Looking back, regardless of the cold weather, it was one of my favorite things we did in Chicago. When we go back, I’d love to experience it again, especially in warmer weather.

 

 

The croissant we had before the boat tour had held us over long enough to finish the tour, so by the time we disembarked the boat, it was lunchtime. We were freezing, so we booked an Uber to take us to Mr. Beef for lunch.

 

Mr. Beef – 666 N Orleans St – (“L” Brown & Purple – Chicago)

 

 

Mr. Beef is a classic Chicago eatery serving Italian beef sandwiches. Mr. Beef is the restaurant that the “The Beef” restaurant from FX’s hit show “The Bear” is based on. I absolutely love the show and wanted to see the original location and of course, try their Italian beef sandwiches. The Italian beef sandwich originated in Chicago. It consists of thin slices of roast beef simmered and served with au jus on French bread. It’s topped with cooked mild or hot bell peppers and the entire sandwich is dipped in the juice the meat is cooked in before serving. When we arrived at Mr. Beef, the line was long but moved quickly due to their efficient service. Make sure you have your order ready at the counter, or they may not be happy with you. For example, before I even finished paying, our sandwiches were ready. We ordered two “Beefs”, or classic Italian beef sandwiches. The seating in the restaurant is in one dedicated room with a long row of tables that are connected to fill the room. All patrons eat close together, giving it a communal feel that is reminiscent of “family style” meals from “The Bear”. The sandwiches themselves are insanely good. Wet, sloppy, full of flavor, and super messy to eat. Italian beef sandwiches ended up being my favorite food from Chicago.

 

 

Art Institute of Chicago – (“L” Orange & Red Lines – Millennium Station)

 

 

After having lunch, our bellies were content but we still hadn’t warmed up after the boat tour, so we took an Uber directly to the Art Institute of Chicago. The Art Institute of Chicago is one of the oldest and largest art museums in the United States, with a collection of art that spans centuries and every corner of the globe.

 

 

They have thousands of art pieces, including iconic paintings, sculptures, photos, textiles, ceramics, medieval armor, Renaissance attire, and more. I purchased our admission tickets online while in the Uber, so when we arrived, we dropped our coats off at the complimentary coat check and went on in. This museum is expansive and you can easily spend the entire day here. We were there for around 3 hours and still felt like we had so much.

 

 

Some iconic art pieces that we got to see there were Grant Wood’s “American Gothic”, Vincent van Goh’s “Self Portrait”,  Pablo Picasso’s “The Old Guitarist”, Claude Monet’s “Water Lillies”, and many more. They had multiple Picassos, Vincent van Gohs, and Monets. While we were there, they had a special exhibit of the iconic painting, “The Great Wave off Kanagawa” by Japanese artist Hokusai. Seeing all of these iconic pieces of art in person and seeing them up close, including every detail and brushstroke was surreal. The Art Institute of Chicago is a must-visit. We stayed and absorbed as much of it as we could until they closed at 5 pm.

 

Giordano’s – 223 W Jackson Blvd (“L” Multiple Lines – Quincy)

 

 

It was dinner time again and one thing we still hadn’t eaten on our trip was the famous deep-dish Chicago-style pizza. We were told by a couple of Chicagoans that deep-dish pizza is a tourist thing, but then again, I’m a tourist, and you can only get deep-dish pizza in Chicago, so we took a short trip on the “L” to Giordano’s. Giordano’s is a famous Chicago pizzeria, serving deep-dish pizza since 1974. Deep-dish pizza is exactly what it sounds like, a deep-dish pizza, but the twist is that the toppings are reversed. The thick deep-dish crust, which is very reminiscent of a pie crust, is first filled with tons of cheese, then your chosen toppings, and finally topped with marinara sauce.

 

We ordered the Chicago classic, which has pepperoni, mushrooms, green peppers, and onions in the middle. Each deep-dish pizza takes 45 minutes to make from the time that you order it, but it was well worth the wait. Deep-dish pizza is impossible to eat without a fork. It’s rich, dense, and very filling. It feels very much like eating a literal pizza pie. We were both full after only eating half of the pizza, so we took the other half of it to go and took the “L” back to our hotel for a quick nap to recharge before finishing our last day in Chicago.

 

John Hancock Tower & Cloud Bar – 875 N Michigan Ave (Uber/Lyft/Taxi)

 

 

The perfect way to finish off our Chicago trip was to go to the top of the John Hancock Tower for some beautiful views and drinks. After our nap, we got dressed nicely and took an Uber to the John Hancock Tower. The John Hancock Tower has had many names across the years. At this time, it’s technically called “875 N Michigan Ave”, which is boring, so I’m using its former name. The John Hancock Tower is the 4th tallest skyscraper in Chicago and the 33rd tallest in the world. The 94th floor is open to the public, offering 360-degree views of Chicago. They offer a thrill ride called “Tilt” where you stand on a glass ledge and hold on while the window tilts out and over the city. I’m scared of heights (and it was dark), so we didn’t do this. We came for the Cloud Bar, a chic and modern bar offering the same 360-degree views of the city.

 

No matter what you go to the 94th floor for, tickets/reservations are required. We purchased a package that gave us general admission to the floor and two cocktails included. It’s not a cheap place to visit, but it’s 100% worth it for the view alone. The elevators that take you up to the 94th floor are incredibly fast and it’s so high up that you can feel the pressure from elevation change as you go up. Once we arrived, we got our cocktails and sat right beside the window, taking in the beautiful city views and enjoying our last bit of time in Chicago.

 

Before going back to our hotel, we decided to go for a final nightcap. There was one brewery left on my list that I wanted to check off, so we took an Uber to Off Color Brewing.

 

Off Color Brewing – 1460 Kingsbury St (“L” Red Line – North/Clybourn)

 

The first time we visited Chicago, when we blew a tire in morning rush-hour traffic, I wasn’t into craft beer very much. We had gone to a grocery store and I saw a bottle of beer on the shelf with a cute little mouse and bees on the label. It was Off Color Brewing’s “Scurry” beer. The label intrigued me so much that I purchased it and ended up loving the beer. It was one of our first road trips together, so I ended up keeping the bottle as a memento. I still have the bottle displayed on a shelf in our house today. I wanted to go to Off Color Brewing to have the beer that intrigued me years ago. Off Color Brewing’s entire aesthetic is artsy and animal-themed, for example, their taproom is called the “Mousetrap”. I had taster glasses of the beers on their menu while we played board games.

 

Their beer is incredible and is easily some of the best in the city, with some of my favorites being their “Beer For Lounging” pale ale, “Beer For Tacos” salt & lime gose, and “Crispy Beer for Pizza” Italian pilsner. I told the bartender about my first Chicago beer coming from Off Color many years ago and he gave me a pint of “Scurry”, that same beer, on the house. Life had come full circle.  

 

It was 11 pm and time to get back to the hotel to pack and rest before our flight back home tomorrow, so we took an Uber back to our hotel.

 

January 4th

 

We woke up around 10 am and checked out. Our flight wasn’t until 5 pm, so we still had a bit of time for one last adventure in Chicago. We left our bags with the hotel concierge and took an Uber to get breakfast.

 

Kasama – 1001 N Winchester Ave (Uber/Lyft/Taxi)

 

 

Venus and I had never been to a Michelin-star restaurant. A couple of locals told us that Kasama, a Michelin-star Filipino restaurant, has spectacular brunch. Their dinner service requires reservations three months in advance but their brunch is first-come first-serve. We took an Uber there to save us some time. Our Uber driver already knew about Kasama and as we pulled up he said that we were “lucky because the line didn’t extend beyond the block”. There was still a line of around 40 people outside of the restaurant and we waited around 45 minutes to get in.

 

 

Kasama’s brunch is known for its exquisite pastries, so we each ordered a pastry, coffee, and breakfast entree. Venus got their pork-belly adobo with garlic rice and I got their Filipino breakfast sandwich with longanisa sausage, egg, and cheese. My sandwich was easily the best breakfast sandwich that I’ve ever had. I got a blueberry muffin-top pastry that was also incredible. The vibe inside Kasama was simple and modern, but cozy. The staff was kind and accommodating. The food is incredible and perfectly balanced. The prices aren’t budget-friendly but they are reasonable for a Michelin-star restaurant. The price and long wait in the cold were 100% worth it though.

 

After brunch, we took an Uber back to the hotel to pick up our bags and headed to the nearest “L” station. We purchased a one-way train ticket and took the 45-minute train ride back to the airport. Our adventures in Chicago had finally come to an end.

 

Chicago is a city that truly has something for everyone – breathtaking architecture, world-class museums, a thriving food and beer scene, and its unapologetic and genuine culture. I’ll never be able to put it into words as well as the late and great Anthony Bourdain did, so I’ll leave you with his:

 

“I spend a lot of my life — maybe even most of my life these days — in hotels. And it can be a grim and dispiriting feeling, waking up, at first unsure of where you are, and what language they’re speaking outside. The room looks much the same as other rooms. TV, coffee maker on the desk. Complimentary fruit basket rotting on the table. The familiar suitcase.

 

All too often, particularly in America, I’ll walk to the window and draw back the curtains, looking to remind myself where I might be, and it doesn’t help at all. The featureless, anonymous skyline that greets me is much the same as the previous city and the city before that.

 

This is not a problem in Chicago.

 

You wake up in Chicago, pull back the curtain and you KNOW where you are. You could be nowhere else. You are in a big, brash, muscular, broad-shouldered motherf*ckin’ city. A metropolis, completely non-neurotic, ever-moving, big-hearted but coldblooded machine with millions of moving parts — a beast that will, if disrespected or not taken seriously, roll over you without remorse.”

 

As always, remember to embrace the unfamiliar, try new things, ask the locals for recommendations, wear your seatbelt, and most importantly, get out and explore.

 

Recommendations

 

Things to Do

 

Honorable Mentions: The Chicago Theatre, Wrigley Field, Garfield Park Conservatory, Walking  & parks on the Lake Michigan lakefront

 

 

Food to Eat

 

 

 

Drinks to Drink

 

Honorable Mentions: District Brew Yards, Cruz Blanca Brewery, Spiteful Brewing, Half Acre Beer Co.

 

Connect with Digital Wax on Facebook, X, Instagram, Threads, and Bluesky.

 

 

About the Author:

 

 

 

– Christopher Brown is a freelance writer for Digital Wax. He grew up in West Virginia and works primarily as a dental hygienist in Charleston. His wife tells him that he has too many hobbies; a musician, hip-hop head, football fanatic, beer brewer, frequent traveler, & master home chef.