Chicago is one of my favorite cities because there are so many amazing restaurants and things to do. Even after visiting the windy city three times in one year, I still can’t wait to make more memories here in the future. Here are some of my favorite activities where you can learn about the abundant architectural and historical landmarks of Chicago, enjoy the melodic tunes of jazz music, explore the huge art collection at the famous Art Institute of Chicago, and more.
Chicago Ghosts and Gangsters Tour
If you want to learn about Chicago’s infamous history of Al Capone, speakeasies, spooky tunnels, and more during the bootlegger era, sign up for the Chicago Ghosts and Gangsters tour. This two-hour walking tour takes you along the Loop region of downtown Chicago so you can step foot into the same buildings and streets that these famous gangsters used to call their stomping grounds.
Our tour guide, Ty, was so animated and intrigued us throughout the tour. He answered so many questions and kept the group entertained. We even got to stop by the Palmer Hotel and bought a brownie from the original recipe by Ms. Palmer, who–spoiler alert–created the dessert for the World’s Fair. This brownie is much closer to fudge than your modern-day version but still delicious.
If you’ve been on any of the architecture boat tours like we have, you’ll notice some overlap with information because it’s all very relevant to Chicago’s history. Despite this, I enjoyed this tour nonetheless and would recommend it to any tourist.
Type of activity: walking tour
Price: $$ ($35 pp)
Neighborhood: The Loop
Address: 71 E Upper Wacker Dr, Chicago, IL 60601
Website | Yelp
SOAR Farmers’ Market (MCA)
Coming from California, I can say we are truly spoiled with year-round farmers’ markets, so imagine my surprise when I found out I visited the SOAR Farmer’s Market (MCA) on the last weekend in September.
This Farmers’ Market is only open from June to the end of September. This small but mighty market is in the Northside and in front of the Museum of Contemporary Art. A handful of farmers were still selling autumnal produce like pumpkins and root veggies. There were also a lot of canned and pickled items available for purchase, like pepper jellies and honey.
Type of activity: farmer’s market
Price: free
Tips: This is only open during the Summer and early Fall months
Neighborhood: Northside
Address: 226 E Chicago Ave, Chicago, IL 60611
Website | Yelp
Chicago Riverwalk
One of the best things to do in Chicago is actually free. The Chicago Riverwalk is a 1.25-mile-long walking path along the Chicago River and is full of fun things for all ages. There are a ton of restaurants on the riverwalk that offer wine and beer and full dinners. After dinner, you can take a stroll along the path and digest.
You can also take a seat at one of the grassy areas to read a book or hang out with friends. It’s also lit up during the night, perfect for romantic strolls after a dinner date. If you’re an adventure seeker, there are companies where you can rent kayaks and jet skis, or if you’ve got kids, there are hot cocoa boats to sit on the river with your steamy drink.
There are many entrances on Wacker Drive, the main street the Chicago River runs alongside, to step down to the Riverwalk, and you can tell by the blue and white labeled gates above every entrance.
Type of activity: landmark
Neighborhood: The Loop
Address: 400 E Lower Wacker Dr, Chicago, IL 60601
Website | Yelp
Green City Market
Chicago has many farmer’s markets across the city, and I like popping into them to see fresh and local goods. One of my favorite markets is the Green City Market in the West Loop. It’s open on Saturdays from 8:00 AM-1:00 PM May through November and is located in Mary Bartelme Park. On hot days, the shade from the trees in the park is perfect for cooling off between shopping and eating.
It’s a smaller-sized market than I’m used to in California, but there’s still tons of stuff to find. This market has lots of jams, honey, and pickled things to give to your friends and family, perfect for unique souvenirs to bring home. My favorite spots were the pet treat booth, which is actually a butcher, and they use leftover parts to make treats for cats and dogs – you know, it’s super fresh and of excellent quality. My cat loved them!
Type of activity: farmer’s market
Price: free
Favorites: fresh seasonal veggies, pickled mushroom booth, pet treat booth
Neighborhood: West Loop
Address: 115 S Sangamon St, Chicago, IL 60607
Website | Yelp
American Writers Museum
It was by chance that I stepped into the American Writers Museum, but I’m so glad I did. This museum is full of interactive exhibits and valuable Chicagoan and US literature information. Inside, you’ll find permanent exhibits, like the Nation of Writers gallery that shows a 400-year timeline of writers and poets.
There are also temporary exhibits focusing on modern literature and writing, like the intersection between writers and gamers that features fantasy worlds of Dungeons and Dragons and other games. You can easily spend 2 hours inside this museum, and it’s a perfect place for families.
This museum is off the corner of North Michigan Avenue and Lake Street. It’s inside a multi-use building on the second floor, but you’ll know you’re at the right entrance when you see signs from the main sidewalk. Tickets start at $14 for adults, and many events are scheduled throughout the month, like author signings and the American Writer’s Festival.
Type of activity: Museum
Price: $ ($14 pp)
Tips: Look for Groupon discounted tickets
Neighborhood: The Loop
Address: 180 N Michigan Ave 2nd Floor, Chicago, IL 60601-7401
Website | TripAdvisor
360 Chicago
If you want to see the fantastic Chicago skyline, visit 360 Chicago. It’s on the 94th floor of what was formerly the John Hancock Center in the Magnificent Mile shopping district. You’ll enter the ground floor, take a relatively fast elevator to the top floor, and instantly be in view of Chicago and Lake Michigan.
If you’re a daredevil, you can buy tickets to TILT, a moving platform of windows that lets you lean outward from the building 1,000 feet above Chicago for two minutes. TILT is an additional $39 on top of admission. For those who just want to relax and see the views, order a drink from Cloud Bar–a bar above the clouds that comes with general admission to 360 Chicago. There are also souvenir shops on the top floor and bottom floor of the building if you want a memento from your visit.
Type of activity: Observation deck
Price: $35 ($$ pp)
Tips: You may be able to find cheap packages for 360 Chicago and architecture tours on websites like Groupon.
Neighborhood: Northside
Address: 875 N Michigan Ave 94th floor, Chicago, IL 60611
Website | Yelp
Shoreline Sightseeing Architecture Boat Tour
You can’t go to Chicago without partaking in an architecture boat tour – or really any activity that deals with boats and the Chicago River and Lake Michigan. Shoreline Sightseeing is one of the two main boating tours in the city and offers an architecture river boat tour, skyline tour, and holiday events. The architecture tour is 60 minutes long, and you ride along the Chicago River listening to a tour guide give you a history lesson on over 40 landmarks and buildings.
This architecture tour was my first boating tour in Chicago, and I learned quite a lot about Chicago history, including the great fire that led to the many beautiful buildings in the city today. I went in mid-May and happily sat in a shaded spot during the tour. Not all boats have shaded areas, so bring a hat and sunglasses.
The skyline tour is mainly a ride on Lake Michigan with a prerecorded lesson where you learn about Northern and Southern landmarks along the lakeside of Chicago. There are also special events like a Winter Fireworks Cruise during November and December. For skyline tours, the entrance is on Navy Pier. For architecture boat tours, the entrance is by Michigan Avenue, past the Apple store.
Type of activity: boat tour
Price: $30 ($$ pp)
Tips: Look on sites like Groupon to find discount prices
Neighborhood: Northside
Address: 401 N Michigan Ave, Chicago, IL 60611
Website | Yelp
The Magic Lounge
Did you know that Chicago is a vast, magic metropolitan? Neither did I until I spent a night at Magic Lounge. It’s quite a ways away from the downtown area that we had to take an Uber to get there, and it’s a speakeasy, so we wouldn’t have known where to stand if it wasn’t for the line forming out the door. But, it is so worth the experience. The interior was well-designed, and it felt like an art deco-style speakeasy. The vibe was very classy, and the staff and hosts were excellent.
The Magic Lounge features three different ways to experience magic: a bar inside the speakeasy with bartenders who simultaneously present magical tricks, a jazz showcase with magic presentations in between breaks (tickets required), and a full-fledged magic show that in itself is two to three stages, depending on where you’re sitting. The latter two require tickets, but you can hop into the bar anytime–be warned that it gets super busy.
The main magic show starts with a cocktail hour and tableside magic, where the hosts also briefly talk to you. There are small snacks and tasty drinks available for purchase. After about 45 minutes, the main show starts on the stage with three performers–including audience participation. If you don’t want this attention, do not sit in the first front rows. However, if you pay more for these front rows, you are invited to a third portion of the show in a smaller theater.
Type of activity: magic club, bar, lounge
Price: $30-100 ($$-$$$ pp)
Tips: Definitely make reservations ahead of time. If you book tickets for the first two rows of the main magic show, there’s an additional show in a smaller venue after the main event.
Neighborhood: Uptown
Address: 5050 N Clark St, Chicago, IL 60640
Website | TripAdvisor
Winter’s Jazz Club
Chicago also has a great music scene. There are a series of jazz clubs and lounges throughout the city, and I visited Winter’s Jazz Club because you can purchase tickets ahead of time, and the vibe seemed super relaxed. There’s no cover charge, but each ticket requires a $10 drink minimum per person.
You’ll find the entrance across from the Ogden Slip in Northside Chicago and off of the River East Art Center Promenade. I picked the last seating at 9:30 PM (if you choose the earlier seating, you can stay for the second show if there’s room). I would recommend this for couples or small groups because the tables are smaller. There are VIP and GA tables, so come early if you want to buy GA tickets so you can be seated in optimal areas. There’s a constant stream of jazz musicians every day, so make sure to check out their calendar to see who is performing.
Type of activity: jazz club
Price: $30 ($$ pp)
Tips: Purchase tickets ahead of time and get there early so you can have better seats because they are first come, first serve for both GA and VIP
Neighborhood: Northside
Address: 465 N McClurg Ct, Chicago, IL 60611
Website | Yelp
First Ascent Climbing (Block 37)
I’ve been indoor rock climbing for over a year now and always keep an eye out for climbing gyms when I travel. I’m glad I brought my shoes to Chicago for this one! First Ascent Climbing is located inside the Block 37 shopping mall on the 4th floor. In California, where I climb, I haven’t seen rock climbing gyms inside a mall–but they seem to be much more common when I travel.
It is incredibly spacious inside, with lockers, showers, and a very new and upgraded facility. The cleanliness and amenities match the nicer gyms I have back home, and I am glad to see a nice option in the city here.
I only visited once, but there were over 200 unique bouldering problems to solve. Perhaps it was from the rainy weather that day, but it was not crowded at all in the late evening. Much like the staff and climbing community back home in CA, everyone here was very nice, and I’d definitely climb here again when I return to Chicago.
Type of activity: indoor rock climbing, bouldering, exercise
Price: $25 day pass ($ pp)
Tips: Day pass gives you lockers with built-in locks and showers. Take the escalator or elevators all the way up to find this gym.
Neighborhood: The Loop
Address: 108 N State St Fl 4, Chicago, IL 60602
Website | Yelp
Cloud Gate (the Bean) / Millennium Park
One of the most famous tourist spots is Cloud Gate in Millennium Park, which sits inside AT&T Plaza. This artwork is by British artist Anish Kapoor. It is inspired by liquid mercury and is famous for its aesthetically appealing, highly polished stainless steel surface that reflects and bends the Chicago skyline and seascapes off its facade. This 110-ton sculpture stands 12 ft high and is nicknamed the Bean because of its curved shape.
Both times I visited Cloud Gate, it was packed with many people, and the reflective surface truly reflects everything, including the crowd. I would recommend visiting during the early morning or later in the evening for clearer photos of the artwork without people.
If you have extra time, take a walk around Millenium Park, especially after a meal, to help you digest. It’s lush green with lots of trees for the perfect amount of shade during humid and hot springs and summers.
Type of activity: landmark, public art
Price: free
Tips: It’s very popular, and if you want photos with fewer people, go very early in the morning or late at night. Sunset photos are also beautiful here.
Neighborhood: The Loop
Address: 201 E Randolph St, Chicago, IL 60602
Website | Yelp
Art Institute of Chicago
The Art Institute of Chicago is a must-do for art lovers during your trip. With over 300,000 works of art and 11 curatorial departments, I could easily spend hours here just wandering around. There are genres for everyone to enjoy, like Egyptian antiquities and Picasso and Jasper Johns.
This museum is enormous, but the main entrance is off Monroe Street across Millennium Park. General admission is more expensive than other art museums I’ve visited, but their collection is so vast I think it’s worth it.
If you’re an Illinois resident or Chicago visitor, discounts are available. You can buy packages with tourist passes, including the Art Institute, architecture tours, and observation towers, like the CityPass.
Type of activity: art museum
Price: $32 ($$ pp)
Tips: if you’re an Illinois or Chicago resident, admission prices can be cheaper or free depending on the day you visit. Make sure to look at the website to check the dates.
Neighborhood: The Loop
Address: 111 S Michigan Ave, Chicago, IL 60603
Website | Yelp
Wendella Boat Tour
I’ve taken the Wendella Architecture Boat Tour twice, and the tour guides are so entertaining. Like the Shoreline Boat Tour, you learn about historical landmarks around the Chicago River. Both boat tours are very similar, and I wouldn’t necessarily pick one over the other. If you can find one at a cheaper rate, I would book that one. Tours are either 45 minutes or 90 minutes, and the latter includes a tour of Lake Michigan. They also offer sunset cruises, fireworks shows, and private cruises.
The Wendella Architecture Boat Tour is perfect for tourists because you can learn so much about the city and also give your legs a break from walking! Typically, these boats don’t have much shade unless you’re in the lower decks (where you won’t see too much action or as much of the skyline), so make sure to bring sunscreen, a hat, and sunglasses. You should also bring a jacket depending on the weather because the river and the lake get breezy.
Type of activity: boat tours and cruises
Price: $27-65 ($$ pp)
Tips: Bring a jacket whether or not it’s hot. Try to find shaded seats during the hot summer months because you’ll get burnt. Bring sunscreen.
Neighborhood: Northside
Address: 400 N Michigan Ave, Chicago, IL 60611
Website | Yelp
Chinatown
Chicago’s Chinatown is about 20 minutes south of downtown if you take the Red Line Metro car, but it’s worth the trip if you’ve never been, especially if you want some home-cooked Asian food. The Metro Station is a block away, and it’s easy to get to and from downtown Chicago.
It’s a smaller Chinatown (30 blocks) than the behemoths I’ve visited in New York City (55 blocks), but it has some worthwhile places to visit. If you want really affordable and delicious dim sum, visit Chiu Quon Bakery. Check out Nine Bar, a speakeasy with Asian-inspired cocktails and snacks for nighttime vibes.
Type of activity: historic region
Price: free
Tips: Get dim sum at Chiu Quon Bakery for a cheap and delicious meal
Neighborhood: Chinatown
Address: 201 W Cermak Rd, Chicago, IL 60616
Website | Yelp
Nine Bar
Tucked inside a restaurant front room in Chinatown, you’ll find Nine Bar, a speakeasy that offers Asian-inspired cocktails and reimagined snacks from your childhood favorites. My favorite items I ordered were the mapo hot fries, chili cucumbers, and McKatsu sandwich. I liked my Paradise Lost drink, which included Thai coconut milk, ube, and pineapple. It was super refreshing.
It’s a bit of a trek to get to if you’re staying in the downtown area of Chicago, but this was one of my favorite bars during my trip. When you walkway, look for the sign that says “Moon Palace,” and you’ll see a bouncer standing outside to check for IDs. It’s a block from the Red Line Metro, so getting here isn’t too much of a hassle. Arrive at 6:00 P.M. to beat the rush of people.
Type of activity: Asian cocktail bar & lounge
Price: $$ ($45 pp)
What to order: mapo hot fries, Paradise Lost cocktail, cucumbers, McKatsu
Neighborhood: Chinatown
Address: 216 W Cermak Rd, Chicago, IL 60616
Website | Yelp
Three Dots and a Dash
Do not miss out on this popular tiki bar. Three Dots and a Dash has been on my list, and luckily, I got to go inside without waiting in line on a Saturday night. However, DO make reservations ahead of time so you can grab a seat instead of standing by the bar drinking your tasty drinks.
You’ll find Three Dots and a Dash in an alley off of Hubbard St. it might be a little tricky to find, but just look for the straw hatch overhang and colorful, tropical murals on the walls. Once you enter, you enter the doorway and walk downstairs to a corridor that separates the tiki bar from the speakeasy, Bamboo Bar (which is reservation only).
Inside, you’ll find a large lounge with tons of seats and a huge bar that makes ordering drinks easy during a busy night. My favorite drinks were the banana daiquiri and the bar’s namesake tiki drink, Three Dots and a Dash. They use fresh and quality ingredients in every drink, so it’s worth it.
Type of activity: tiki bar
Price: $$ ($35 pp)
What to order: banana daiquiri, three dots and a dash
Neighborhood: North Side
Address: 435 N Clark St Back alley on Hubbard St, Chicago, IL 60654
Website | Yelp
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