Looking for the best things to do in Chicago? You’re in the right place.
We’ve heard so many great things about visiting Chicago that we finally decided to put the rave reviews to the test. Last September, we spent an entire month in the Windy City in search of the best the city had to offer. Luckily for us, our good friends live in Chicago and their list of recommendations didn’t disappoint.
Alas, the list below is a combination of recommendations from (happy) locals sprinkled with a few iconic things to do in Chicago that we ended up loving more than expected. On that note, let’s dive in!
Best Things to Do in Chicago
(Table of Contents)
Visiting Chicago (Table of Contents)
- Best Things to Do in Chicago
- Stroll the Chicago Riverwalk
- Go Brewery Hopping
- Take the (Famous) Architecture River Cruise
- Go on a Scenic Bike Ride Along Lake Michigan
- Explore Lincoln Park
- Visit the Art Institute of Chicago
- Enjoy Millennium Park (The Bean)
- Try Deep Dish Pizza
- Walk the Magnificent Mile
- Take in the Views from John Hancock Observatory
- Grab Drinks at Cindy’s Rooftop Bar
- Try the (Famous) Burger at Au Cheval
- Take a Photo at the Start of Route 66
- Catch a Broadway Show
- Order the Italian Beef Sandwich at Al’s Beef
- Catch a Cubs Game at Wrigley Stadium
- Extra Time? More Fun Things to Do in Chicago
- Restaurants to Try While Visiting Chicago
- Chicago Best Things to Do (Post Summary)
- Map of Cool Places to See in Chicago, Illinois
Stroll the Chicago Riverwalk
Perched on the banks of Lake Michigan, there’s no denying that Chicago is a beautiful city. Largely thanks to the Chicago River, which adds a ton of charm to the downtown core and serves as the heart of the city.
Considered an engineering feat, the river originally flowed into Lake Michigan, but a severe storm in 1885 caused the river to empty sewage-polluted water into the lake. Something had to be done.
After the unfortunate event, plans were made to reverse the river’s flow by constructing a canal. The end result? A river that flows inland, serving as a testament to modern engineering.
The scenic riverwalk is dotted with charming cafes, wine bars and cool restaurants. Park yourself at an outdoor table and people-watch for an hour or two. Chicago has an endearing easy-going vibe to it, don’t rush the experience!
Local’s Tip: While strolling the Riverwalk, you’ll probably come across City Winery. A beautiful winery with great outdoor seating right along the water. Why not pop in for a glass of chilled rosé while plotting the rest of the day?
Go Brewery Hopping
Hailing from Portland, I found the breweries in Chicago irresistible, this is a beer town through and through. Home to more that 160 breweries, the variety spans the gamut. From small-batch craft breweries to nationally-famous brand, you won’t go thirsty while visiting Chicago.
We tried 10 different breweries during our month long stay, clear standouts were Revolution, Half Acre Beer Company, Dovetail Brewery, Hop Butcher and Goose Island. I’m thinking about writing a quick recap and ranking of the breweries we visited, will keep you posted!
Take the (Famous) Architecture River Cruise
Chicago is known as the birthplace of skyscrapers and is home to an interesting mix of architectural styles (including works by legendary architects like Frank Lloyd Wright and Louis Sullivan.
The architecture river cruise navigates along the Chicago River and provides insightful history of the city’s most famous buildings, touching on a century of architectural innovation and design.
Some of the best advice I received while narrowing down my list of the best things to do in Chicago was to sign up for an architecture river cruise early in the trip (preferably the first day).
The logic, it seems, is that taking the tour early on gives you a better understanding of Chicago’s layout, which makes it easier navigate the city on foot later.
Long story short, we’re glad we listened to the advice. Learning about the city, by boat, made it much easier to navigate our way around while visiting Chicago for the first time.
Go on a Scenic Bike Ride Along Lake Michigan
Surrounded by formidable Lake Michigan, Chicago has 28 glorious miles of shoreline ripe for exploration. From piers and harbors to beaches and shady parks, everyone can find something to enjoy near the water.
If you’re looking for adventurous things to do in Chicago, I suggest learning about the Lakefront Trail. Sandwiched between Lake Michigan to the east and Lincoln Park to the west, this biking (and walking) trail offers unparalleled views of the iconic city landscape.
Renting a bike (called Divvy Bikes in Chicago) couldn’t be easier. Simply find a bike docking station and follow the instructions to rent. You can opt to pay by the minute or get a day pass, pricing info available here. It’s a great time!
Explore Lincoln Park
Exploring Lincoln Park is one of my favorite things to do in Chicago. The park stretches along Lake Michigan and has a ton of walking/biking trails, ponds and lawns (great for picnics). The park is apart of the Lincoln Park neighborhood, full of tree-lined streets, historic architecture, cute boutiques and great restaurants.
One of the coolest things about Lincoln Park is the free park zoo. Since admission isn’t charged, this is effectively one of the best free things to do in Chicago for families. Established in 1868, it stands as one of the oldest zoos in North America.
Spread over 35 acres, the zoo is home to a wide range of species, from big cats and polar bears to reptiles and primates. Beyond animal exhibits, the zoo engages visitors with interactive educational programs, conservation efforts, and seasonal events like the enchanting ZooLights during the holiday season.
Walk the Magnificent Mile
Michigan Avenue, colloquially referred to as Magnificent Mile, is a shopper’s paradise that extends from the Chicago River to Oak Street in the north. If you’ve been to New York City, this is the equivalent of 5th Avenue.
Spanning 13 blocks, the area is peppered with luxury stores, top-notch restaurants and quaint cafes. Lined with historic buildings, stunning skyscrapers, and charming boutiques, going window shopping along the Magnificent Mile is one of the most popular things to do in Chicago.
While exploring the area, take time to admire the historic Water Tower, it’s one of the few structures to survive the Great Chicago Fire of 1871. There’s also a ton of great hotels in the area, but expect to pay a premium to stay in this opulent area.
Visit the Art Institute of Chicago
Dating back to 1879, the Art Institute of Chicago is an impressive museum that features nearly 300,000 works of art (including world-famous paintings). It’s the 3rd largest museum in the county!
Heck, the building alone is worth the visit. Flanked by two bronze lions on either side, walking the majestic steps towards the entrance feels like a treat.
If you’d like to admire the art, I suggest allocating at least 2-4 hours for a self-guided tour. It’s easy to get overwhelmed if you don’t have a game plan because the musuem is so large. There’s so much to see, you can spend a full day exploring and barely scratch the surface — priority is the name of the game.
If you need a starting point, I suggest making an effort to see the following paintings:
- Georges Seurat’s A Sunday on La Grande Jatte
- Vincent van Gogh’s The Bedroom
- Edward Hopper’s Nighthawks
- Grant Wood’s American Gothic
- Pablo Picasso’s The Old Guitarist
- Gustave Caillebotte’s Paris Street; Rainy Day
You don’t need to be an art connoisseur to know that visiting this incredible museum is one of the best things to do in Chicago. Make sure to pop into the Thorne Miniatures Rooms in the basement. As the name suggests, it’s a collection of super interesting and ornate miniature rooms, a very fun and unique concept!
Enjoy Millennium Park (The Bean)
Millennium Park opened in 2004 in celebration of the new millennium (construction ran 4 years behind schedule), timelines aside, it’s the most visited spot in Chicago, but not without reason! The park is beautiful and well-maintained, making it a joy to explore.
Neatly sectioned off, the park has four areas worth checking out:
- The Jay Pritzker Pavilion (a band-shell music venue hosting talented musicians)
- The Crown Fountain (very cool interactive video sculpture with fountain)
- The Lurie Garden (peaceful garden full of spring blooms)
- Cloud Gate (better known as The Bean)
The Bean is arguably the most iconic landmark in Chicago. As such, learning a bit about it (and grabbing a photo) is a must-do for any Chicago bucket list. Designed by world-renowned artist Sir Anish Kapoor, you may be surprised to learn that the sculpture is actually called Cloud Gate, not The Bean.
But alas, public opinion wins this round — everyone calls it The Bean. Regardless of what you choose to call it, know that seeing this massive stainless steel sculpture in person is one of the most iconic things to do in Chicago.
One of the most interesting things I learned while visiting Chicago was that it cost $23 million to build the thing! (I don’t have the slightest idea why.)
Fun Fact: Millennium Park was built on top a parking garage and rail lines. On this technicality, it’s considered the largest rooftop garden in the world.
Try Deep Dish Pizza
First things first, what exactly is deep dish pizza? Unlike traditional pizza, deep-dish pizza stands out for its hearty crust (buttered with a heavy hand, the crust reminds me of a pie crust) which serves as a blank canvas for generous portions of toppings, starting with cheese and chunky tomato sauce.
The ingredients are placed in the opposite order of a traditional pizza. It goes like this: crust, thick slices of mozzarella cheese, toppings of choice (meats, veggies) and then everything is topped with chunky tomato sauce to end things on a high note.
As with most things, the origins of deep dish pizza are murky at best. The exact dates (and people) responsible for the invention are contested to this day, the only fact everyone seems to agree on is that this iconic dish hails from Chicago.
There’s a few classic joints worth knowing about: Giordano’s, Malnati’s and Gino’s East. However, the jury’s still out on the cream of the crop. Regardless, the pizza is delicious and it’s hard to find elsewhere, which is why grabbing a pie is one of the most popular things to do in Chicago for first time visitors.
If helpful, we tried a handful of great spots while visiting Chicago and liked Uno’s the best.
Take in the Views from John Hancock Observatory
Soaring to impressive heights on the 94th floor of the John Hancock Center, The John Hancock Observatory (officially known as 360 Chicago) offers one of the most remarkable panoramic views of the Windy City. From this vantage point (1,000 feet in the sky) you’ll see four states: Illinois, Indiana, Wisconsin, and Michigan.
With high-speed elevators that ascend to the observation deck in just 40 seconds, the observatory attracts over 550,000 visitors annually, making this one of the most popular attractions in Chicago.
Grab Drinks at Cindy’s Rooftop Bar
When it comes to the best rooftop bars in Chicago, both locals and visitors agree that Cindy’s can’t be beat. Located atop the Chicago Athletic Association Hotel, the bar offers incredible views of Millennium Park, the Art Institute of Chicago and Lake Michigan.
The food menu is centered around American cuisines using seasonal and locally-sourced ingredients, but the exciting libations is where they truly shine. We enjoyed some creative cocktails at the rooftop at Cindy’s and can confirm that this is one of the most relaxing things to do in Chicago.
Try the (Famous) Burger at Au Cheval
My husband and I currently live in the Big Apple and recently went on the hunt for the best burgers in NYC. The winner? Au Cheval. We were surprised to learn that the restaurant hails from the Windy City, so we made it a point to swing by while visiting Chicago.
A traditional burger with double patties and sharp cheddar, you’ll also get the option to add bacon and an egg. The bacon is thick enough to be a meal itself, and the runny egg bursts on the first bite, adding another delightful layer to the glorious creation. The lines are long for a reason, this is a must-do in Chicago for foodies.
Take a Photo at the Start of Route 66
Alright, you don’t have to be retired to understand the allure and hype surrounding Route 66. The most iconic road trip in America (considered one of the best in the world), the official road no longer exists, but that doesn’t stop folks from embarking on the adventure regardless.
The route officially starts in the Windy City (at Adams Boulevard), which is why popping over to take a photo is one of the best things to do in Chicago. I mean, when else will you get the chance? The sign is found just across the street from the Art Institute of Chicago (two birds, one stone).
Catch a Broadway Show
One of my biggest surprises while visiting Chicago for the first time was becoming aware of Broadway shows. Much like NYC, I knew I could catch popular shows while visiting Chicago, but unlike NYC — they’re much more affordable. Admittedly, Chicago’s theater district is much (much) smaller than New York’s, but it punches above its weight (it’s world-class entertainment!).
Order the Italian Beef Sandwich at Al’s Beef
My brother-in-law is from Chicago. His family currently lives in the city, so we asked them about the best things to do in Chicago. They got back to us in record speed (seems they have a handy list for out-of-town visitors always at the ready) and informed us that ordering the beef sandwich at Al’s Beef was non-negotiable.
And who are we to argue with locals?
A celebrated Chicago institution since 1938, Al’s Beef makes some of the best Italian beef sandwhiches in the Windy City. Succulent thin slices of seasoned roast beef, simmered and served au jus on a long Italian-style roll, it’s as delicious as it sounds. Elevated by the optional addition of giardiniera (sweet green Italian peppers), which I wouldn’t sleep on.
If you’re a foodie in search of the top places to visit in Chicago, Al’s Beef should be on your list.
Catch a Cubs Game at Wrigley Stadium
The beloved home of the Chicago Cubs since 1916, Wrigley Field is one of the most iconic baseball fields in the country, catching a game here is a quintessential Chicago experience. Located in the charming Lakeview neighborhood, the stadium opened in 1914, making it the second-oldest Major League Baseball park in the United States.
Attending a Cubs game is an opportunity to partake in longstanding traditions, from singing “Take Me Out to the Ball Game” during the 7th-inning stretch to celebrating home runs and victories alongside a loyal (and rowdy) fans.
So whether you’re a die-hard baseball fan or simply looking to soak up an authentic piece of the city’s culture, catching a game at Wrigley Field is one of the best things to do in Chicago.
Extra Time? More Fun Things to Do in Chicago
Enjoy a Classic Chicago Dog at Johnnie’s Beef
Similar to deep dish pizza, you know the drill: Anyone visiting Chicago for the first time needs to get their grubby little hands on a classic Chicago dog. Which begs the question — what’s the difference between a Chicago dog and a regular hot dog?
Glad you asked, it simply comes down to toppings and the bun (Chicago dogs are served in a sesame bun). A proper Chicago dog has specific set of ingredients that distinguish it from its regular cousin.
As for the toppings, these bad boys are topped with a vibrant array of condiments including yellow mustard, bright green relish, fresh chopped onions, juicy tomato wedges, a pickle spear, sport peppers, and a dash of celery salt. One key ingredient missing? Ketchup, you won’t find it here.
Johnnie’s Beef is located in Elmwood Park (30-minute drive from downtown), but is completely worth the trek because it’s one of the best things to do in Chicago for foodies. Renowned for Italian beef sandwiches and Chicago-style hot dog, this place is a favorite among locals.
A classic Chicago dog at Johnnie’s Beef adheres to tradition: an all-beef frankfurter on a poppy seed bun, topped with generous helpings of traditional toppings. And yes, it’s as gluttonous as it sounds!
Enjoy Live Jazz at The Green Mill
The Green Mill is a legendary jazz club located in the Uptown neighborhood. With a history dating back to 1907, it stands as one of the oldest continuously operating jazz clubs in the country, reason alone to visit! The venue became a hotspot during the Prohibition era, reputedly frequented by infamous gangster Al Capone.
Performances are held almost every night of the week and the music spans various jazz genres, including traditional, swing, bebop, and modern styles. If you’re a fan of jazz, swing by the Green Mill while visiting Chicago.
Walk the 606
The 606 is a pretty innovative urban park built atop a former elevated rail line that stretches 2.7 miles.and connects four neighborhoods: Logan Square, Humboldt Park, Bucktown and Wicker Park. Opened in 2015, the trail is lined with art installations, gardens and plenty of gathering spaces. It’s a great place to stretch your legs while admiring the city’s commitment to public parks.
Visit Garfield Park Conservatory
Garfield Park Conservatory is one of the largest conservatories in the country, spanning 4.5 acres of indoor gardens. Opened in 1908, it was designed by renowned landscape architect Jens Jensen, and is home to thousands of plant species from around the world.
Take your time exploring the distinct ecological habitats of different plants, including the Fern Room, Palm House, and Desert House. Garfield Park Conservatory also serves as an educational resource, offering a variety of programs, workshops, and events aimed at promoting environmental awareness.
If you consider yourself a green thumb, you can probably see why visiting Garfield Park Conservatory is included on our list of the best things to see in Chicago.
Restaurants to Try While Visiting Chicago
Chicago is a food lover’s paradise. There’s no shortage of great restaurants to try, but if you’d like some direction, here’s a list of the restaurants we enjoyed most while visiting Chicago.
- Green Street Meats (Texas BBQ)
- Birrieria Zaragosa (Mexican)
- Bavette’s (Steak)
- Cicco Mio (Italian)
- Kasama
Chicago Best Things to Do (Post Summary)
In sum, here’s a list of the best things to do in Chicago, hope you enjoyed!
- Stroll the Chicago Riverwalk
- Hop aboard the (famous) architecture boat tour
- Take a scenic bike ride through Lincoln Park
- Visit the Art Institute of Chicago
- Enjoy Millennium Park (see The Bean)
- Get your hands on a deep dish pizza
- Walk the Magnificent Mile
- Grab a beer at the Navy Pier Beer Garden
- Take in the views from the John Hancock Observatory
- Take a photo at the start of Route 66
- Visit the Lincoln Park Zoo
- Grab drinks at Cindy’s Rooftop Bar
- Have a classic Chicago dog at Johnnie’s Beef
- Try the (famous) burger at Au Cheval
- Order the Italian Beef (sandwich) at Al’s Beef
- Catch a Broadway Show
- Catch a Cubs game at Wrigley Stadium
- Enjoy live jazz at The Green Mill
- Walk the 606
- Visiting Chicago with a green thumb? Visit Garfield Park Conservatory
What do you think?