21 of the Best Things to do in Chicago

Looking for things to do in Chicago? There are few cities more spectacular than Chicago. Nestled on the banks of Lake Michigan, Chicago has everything from sandy beaches and luxury shopping districts, to vibrant cultural scenes and art galleries, there is something for everyone. From fancy shops like Tiffany & Company on Michigan Avenue to quiet neighborhoods like Andersonville and Hyde Park, the city of Chicago is where you’ll find an unequaled travel experience.

Best Things to do in Chicago

The Windy City is a fabulous year-round destination for those who crave art, culture, adventure as well as world-class restaurants and hotels. With so much to see and do in Chicago, it’s hard to fit it all in one trip! Here are my favorite things to do in Chicago including where to eat!

1. The Bean – Millennium Park and the Cloud Gate

The Bean at Millennium Park is perhaps one of the most iconic sculptures in Chicago, or at least that’s how it’s described by most visitors. It’s actually named the “Cloud Gate”, created by the world-famous sculptor, Anish Kapoor. Visit the beautiful Millennium Park to take advantage of a wonderful photo op with The Bean, it’s gleaming mirrored finish makes a wonderful backdrop as it seems to creatively distort the city’s skyline.

While at Millenium Park, you can’t miss the magnificent Crown Fountain and its two 50 foot glass towers bookending the reflecting pool. The Crown fountain towers showcase video projections of Chicago faces and life.

A fun way to get around while doing a tour of Chicago is by Segway. This highly rated segway tour is perfect for first time visitors to Chicago where you’ll visit Millenium Park, Grand Park, the famous Buckingham Fountain and you’ll ride to Museum Campus to soak up spectacular skyline views of the Chicago and its beautiful lakefront trail.

3. Art Institute of Chicago

In the center of Grant Park, on famous Michigan Avenue, this architectural masterpiece is easily accessible with the Chicago CityPASS. Just walk between the two lion statues and step into an amazing collection of art from around the world. The Art Institute was voted the #1 Museum in the World by Trip Advisor and it’s easy to see why when you gaze at masterpieces by Chagall, Matisse, and Georgia O’Keefe. Located in the Loop community of Chicago’s Central Business District, there are plenty of things to see in and to in this area.

Get your skip the line tickets in advance where you’ll enter 30 minutes before the museum opens to meet your guide and see iconic pieces by Picasso, Salvador Dali and Andy Warhol. The Art Institute of Chicago has one of the greatest collections of impressionist art in the world. You can book with peace of mind for a full refund should you decide to cancel within 24 hours of the activity.

Things to see Around the Central Business District of Chicago

• Grant Park – Grant Park is a large urban area in the Central Business District of Chicago
• Buckingham Fountain –
• Agora – Public art installation of 106 headless and armless iron sculptures
• Petrillo Music Shell – Hosting many festivals such as the Chicago Jazz and Blues Festival and Lollapalooza
• Maggie Daley Park – If you visit in winter be sure to try out the skating loop.

4. Sky Deck Chicago at Willis Tower

To get unparalleled views of the Chicago skyline, suburbs and Lake Michigan, visit the Sky Deck, high atop the Willis Tower (formerly known as Sears Tower). Visit on a clear day to see planes take off and land at O’Hare. If you’re feeling adventurous, hang over the city on the ledge, a glass enclosure with a clear floor, you’ll feel like you’re floating 103 floors above it all.

You can get Fast Pass tickets in advance. When you visit the iconic tower, you’ll learn about Chicago’s history and architecture. The elevator has a multimedia display. Make sure to download the Skydeck Mobile App to show famous Chicago Landmarks. The pass includes, Timed access to the Skydeck, access to The Ledge, Free Wifi, Theater presentation and express entry and priority access. (When choosing fast pass option)

5. Chicago Magic Lounge 

From a converted 1940s, commercial laundry grew the Chicago Magic Lounge, a 7,200 square-foot, art deco-style, theatre, and lounge. It features a 1930s-style speakeasy performance bar, a 120-seat cabaret theatre and a formal close-up gallery named The 654 Club.

Every polished inch of this elegant new nightclub is dedicated to the art of “Chicago-Style Magic”. Don’t miss this Lounge, it’s highly entertaining, full of tasty tid-bits, delicious cocktails, amazing sleight-of-hand, and a whole lot of fun.

One of our favourite things to do in any city is to take a walking tour with a local guide. Chicago is a foodie city and this walking tour lets you discover the best of Chicago as you tour the city’s vibrant food scene. You’ll see the Chicago Theatre made famous in the musical Chicago, where you’ll enjoy food as you learn of the city’s history. Sample everything from the Chicago style hot dog, Chicago style deep dish pizzas, popcorn and a classic Chicago sandwich.

6. Navy Pier

Be sure to make a stop at the Navy Pier, another iconic city landmark. It’s had 180 million visitors in the last 25 years who’ve enjoyed the Pier’s 50 acres of attractions and experiences. To get a birds’-eye view of the city jump on the Centennial Wheel, a 200-foot Ferris wheel with enclosed gondolas enabling year­ round fun for the whole family no matter the weather.   

With the Navy Pier Express ticket you’ll get a fast pass express ticket to ride the wheel. Located at the Historic Navy Pier, be suspended over Lake Michigan at the mouth of the Chicago River. The Centennial Wheel was built in 2016 to celebrate the 100th anniversary of the Navy Pier opening.

Navy Pier is one of the best places to visit in the city. It is a waterfront event space housing year-round attractions. This family-friendly destination has the Pier Park amusement park where kids can ride the historic carousel, the Wave Swinger or the Centennial Wheel. A 200-foot Ferris wheel that has enclosed climate-controlled gondolas offering beautiful views of downtown Chicago.

7. Chicago Cultural Centre

If you love Chicago’s stunning architecture, you must visit to the Chicago Cultural Center. This breathtaking building is the home of two magnificent stained-glass domes and stunning rooms showcasing it’s past.

Designed in the Classical Revival style the dazzling interior has a Tiffany art glass dome, mother of pearl mosaics and a Carrara marble lobby. They offer free exhibitions, music, dance, and theatre events.

Chicago has a colorful criminal past with some of the most notorious crime bosses in history. This Chicago crime boss tour is one of the more unique things to do in Chicago. Ride through the Windy City by bus to see the areas frequented by the likes of Al Capone, John Dillinger, and the Terrible Tommy O’Connor. You’ll see mob staples like the Bigraph Theatre, Holy Name Cathedral and the Site of the St. Valentine’s Day Massacres.

8. Catch a White Sox Game

Baseball is a way of life in Chicago and you can’t do Chicago in spring without experiencing a White Sox Game. Guaranteed Rate Field is always filled with enthusiastic fans who cheer on their team while munching hotdogs, burgers and beer.  For tickets and game schedule check out the Chicago Whitesox website.

9. Wrigley Field

Or catch the Chicago Cubs play a game at the historic Wrigley Field. Chicago is blessed with two major league baseball teams. Wrigley Field is the second-oldest ballpark in the major league. It sits in a residential neighborhood of Chicago close to Lake Michigan.

10. Chicago Architecture River Cruises

One of the best things to do in Chicago is to take a tour of the city on the Chicago River. The Chicago Architecture River Cruise, also included with the CityPASS is one of the top attractions in the city. Chicago, known for its rich architectural history, is home to some of the world’s most iconic buildings and world-famous architects.

During the 90-minute sightseeing boat tour, you will see and learn the history of over 50 buildings, bridges, and historic sites. You’ll hear all about Chicago from the Great Chicago Fire to the modern city that rose out of its ashes. There are some 50 buildings located on the Chicago River from historic gems to state of the art skyscrapers.

• Fun Fact: Chicago has a large Irish community and during Saint Patrick’s Day the city dyes the Chicago River green to celebrate. check out these Facts About St. Patrick’s Day

11. Chicago Riverwalk

Take a stroll along the Chicago River downtown on the Chicago Riverwalk. The Chicago Riverwalk is a 1.25 mile long path that runs through There are shopping, dining, and museums along the path. Plus, it is easy to catch a boat tour from the Riverwalk to take in the sites in comfort.

Take a Chicago Food Tour

A great way to explore Chicago by foot is to book a guided food tour. This guided tour takes you from the Chicago Theater to the Chicago Pedway where local commuters move about the city’s underground tunnels. You’ll then walk from City Hall to the Chicago Riverwalk where you’ll see famous landmarks such as the Marina Towers, the Britannica Building, and the Willis Tower.

It’s then on to part two of the Chicago City tour with food tastings in the River North Neighborhood to sample Chicago staples like the Chicago hot dog, popcorn, and Chicago style deep-dish pizza. Bring your appetite because tehre’s a lof to food on this tour.

13. John Hancock Center

Offering the best views of the city skyline is the observation deck of the John Hancock Center. Get a thrill at Tilt where you get a downward facing view of the city from 1,030 feet up in the air. Grab a drink at bar 94 and take in the 360 degree views of the skyline and Lake Michigan from its 17,000-square foot observation deck.

14. The Magnificent Mile

The ‘Mag Mile’ is a mile long street boasts over 460 retailers including restaurants, major department stores, popular brands, luxury labels and designers as well as three vertical shopping centers, museums and the Loyola University. It is one of the most popular shopping districts in the city.

This 13-block stretch of North Michigan Avenue is one of the city’s cultural hubs. You can also see historical gems like the Water Tower and Pumping Station as well as two of the survivors of the 1871 Chicago Fire. Get the full experience complete with lake views by walking the entire mile.

See more of Chicago by booking a tour with ‘Inside Chicago Walking Tours’; they do an incredible job of telling Chicago’s story in an engaging, entertaining way. They’ll tell you some fascinating details about different buildings and areas in the city.

15. The Second City

This legendary comedy club launched the careers of Bill Murray, Eugene Levy, John Belushi and Catherine O’hara and so many more great comedians of our time. Located in the Lincoln Park neighborhood of Chicago, this is one of the top rated things to do in Chicago.

The Second City in Chicago is the original comedy club, but there are Second City’s in Toronto and Hollywood. It was the inspiration for Saturday Night Live and you name a comedian, chances are they worked on their comedy chops here.

17. Garfield Park Conservatory

Garfield Park Conservatory is one of the largest gardens under glass in the world. What makes it even more of a feat is that is was built in 1908. It is often referred to as a “landscape art under glass”

Inside it feels like a tropical rainforest with palm trees and ferns sprawling across 10 acres of gardens, and ponds both indoors and out.

18. Museum of Contemporary Art

Filled with interactive exhibits, performances, and programs, the Museum of Contemporary Art is a must-stop on your visit. The MCA is one of the worlds largest art museums, housing over 2,000 works. They take pride in featuring new and experimental work in all types of media.

Over the summer Virgil Alboh’s “Figures of Speech” exhibit drew thousands of visitors who viewed this gender-bending artist/designer’s work.  In fact, the exhibit was extended a few more weeks in September 2019, so audiences could take in the Chicago natives work.

19. Museum of Science and Industry

Located in the Hyde Park area of Chicago in the former Palace of Fine Arts from the  1893 World’s Columbian Exposition, the Museum of Science and Industry is the largest of its kind in the Western hemisphere. See a World War II German submarine that was captured during World War II, walk through a replica of a coal mine and run on a human sized hamster wheel.

One of the coolest new exhibits in the Museum of Art and Industry is the 100 Lego sculptures created by artist Nathan?Sawaya. See recreations of masterpieces such as The Mona Lisa, Michaelangelo’s, David, and a giant dinosaur made out of Lego.

20. Field Museum

Families always love a Natural History Museum and the Field Museum of Chicago has everything from an Egyptian tomb to dinosaur exhibits. Opened in 1894, the field museums showcases exhibits dating back 4.6 billion years. From China to Ancient Egypt you’ll trace the history of the world. The star attraction is the most complete T-Rex fossil ever discovered.

21. Lincoln Park

Lincoln Park is one of the best places in Chicago to enjoy the great outdoors. There are many things to do in Lincoln Park from perusing the exotic flowers and plants of the Lincoln Park Conservatory to seeing the animals and flamingoes of the Lincoln Park Zoo and walking along the Lakefront Trail. You can really spend an entire day in just this one neighborhood.

This expansive park and neighborhood houses the Peggy Notebaert Nature Museum and the Chicago History Museum and the Armitage and Halsted is one of the popular shopping districts in the city with plenty of shops and boutiques.

The Lincoln Park Zoo is said to have a haunting in its bathroom and you can visit it by taking the Lincoln Park Ghost Tour. The bathrooms mirrors at Lincoln Park Zoo is said to be home to the ghost of the Woman in White. Visit 8 historic sites including the forgotten burial ground, and learn about the gangsters of Chicago and the spirit that haunted Al Capone.

Where to Eat in Chicago

Whether you crave street food or fine dining, there are many Chicago restaurants to choose from. Don’t miss the world-famous Chicago Red Hot or a Chicago Deep Dish Pizza, like the one I had at Lou Malnati’s.  Check out where to eat in Chicago by local writer Lisa Lubin.

Purple Pig

How could you go wrong with a restaurant having a tag line like ‘Cheese, Swine and Wine’ – all our favorite things! Located in Downtown Chicago, the Purple Pig is my choice for the best things to do in the city.

Try the charcuterie board or Ham Croquettes, Salt-Roasted Beets with Whipped Goat Cheese + Pistachio Butter, Lamb Ribs Harissa BBQ, Lime Yogurt + Fregola, Pork Belly + Tenderloin Ginger Glaze, Carrot + Espresso.  No matter what you order it’ll be extremely well-curated.  

Lou Mitchell’s

The skillet eggs, hot coffee and heaping stacks of pancakes have been a staple of this historical diner since 1923. Specializing in breakfast, lunch, and brunch, this Chicago staple is not to be missed. Plus kids will love the free Milk Duds and adults will enjoy their delicious donut holes.

Michael Jordan’s Steak House

If you love steak then this is the place to be. Located in the InterContinental Hotel it features an extensive wine list.  Steak choices come in Slagel Farms NY Strip, New York Strip, Fillet Mignon and an Aged Porterhouse. The menu has an exhaustive list of starters and sides but save room for the signature 23 layer chocolate cake.

Rooftop Bars

In case you haven’t noticed Chicago also has a happening bar scene where craft cocktails are all the rage. In a city as amazing as Chicago, you should enjoy your drink with a view.

• Suggested rooftop bars for great views of the city include:
  • Try LH on 21 at London House
  • Cindy’s Rooftop at Chicago Athletic Association Hotel
  • The Raised Bar, Chicago.

Lou Malnati’s

Never leave Chicago without trying at least one deep-dish pizza, a Chicago staple for as long as one can remember. Lou Malnatti’s does deep-dish pizzas very well. Start with a delicious green goat cheese salad and finish with your selected pizza. Wash it all down with house made Iced tea – they have gluten-free pizza as well. 

Portillo’s Hot Dogs

Portillo’s has been around since the early ’60s and it’s the best place to try one of Chicago’s famous hot dogs. Enjoy it any way you like with chili, hot peppers or just plain.  Don’t like the “dog” then there’s salads, pasta, and chicken on the menu as well. The line ups at Portillo’s is long at lunchtime but they do move fast. 

Where to Stay in Chicago

Wondering what hotel complements your stay in Chicago? In one of the most prime locations in the city, the InterContinental Chicago is a destination on its own with a door on the Magnificent Mile. Walking into the InterContinental Chicago, you step back in time – to old Chicago with all its glitz and glamour.  

The Intercontinental Chicago has one of the best views of Chicago. Enjoy breathtaking views from the Tower Lounge on the 32-floor; a steak in the sophisticated atmosphere of Michael Jordan’s Steak House. Or visit the master sommelier who creates wine tastings paired with perfect treats at Eno Wine Room.

While there enjoy the 1920’s era pool or a relaxing massage at the spa. The InterContinental is centrally located to everything the Magnificent Mile has to offer – from shops to dining and all the attractions.

See more reviews of Chicago on TripAdvisor / Booking.com

Getting Around the City of Chicago

The fastest and most efficient way to get around Chicago is using the L-Train. The elevated train system also operates out to O’Hare International Airport.

You can also get around Chicago from May to Oct/Nov (depending on weather) via water taxi. Uber operates in Chicago.

Another way we love to get around when visiting a city for the first time is to book a hop on hop off bus tour. It let’s you see all the city highlights with one affordable bundle. This double decker bus goes by the Willis Tower, Wrigley building, the Shedd Aquarium and Field Museum as well as driving down the Magnificent Mile. You’ll also travel across the Michigan Avenue Bridge over the Chicago River connecting the north and south sides of Chicago.

Purchase 24 or 46 hour tickets and hop on or off as you choose to see the top tourist attractions in Chicago.

As you can see, there are so many amazing things to do in Chicago and we’ve barely scratched the surface. But if you are planning a trip to the Windy City, this guide is a great start for first time visitors to see the best that Chicago has to offer.

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