Chicago will always be one of my favorite cities. I grew up visiting my grandparents here and have fond memories of swimming in Lake Michigan and visiting the museums. My own parents moved to the Chicago suburbs when my kids were young, and I loved taking them into the city and creating lasting childhood memories for them as well. Putting this post together was a fun excuse to dive deep into my archives to find pictures of past visits when my kids were so little!
Over the years, I’ve also taken girls’ trips to Chicago and traveled here for volleyball tournaments, so I’m no stranger to the city! After numerous visits, I have finally put together the ultimate Chicago bucket list, featuring the best places to go and things to do in the city!
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25 Bucket List Places to Go & Things to Do in Chicago
Table of Contents
- Millennium Park
- Wrigley Field
- Architecture Boat Tour
- Chicago Riverwalk
- North Avenue Beach
- Navy Pier
- Shedd Aquarium
- Lincoln Park
- Magnificent Mile
- Willis Tower Skydeck
- Chicago Deep Dish Pizza
- Chicago “L” Train
- Field Museum
- Chicago Theater
- Grant Park
- Lakefront Trail
- Chinatown
- Garrett’s Popcorn
- Adler Planetarium
- McDonald’s Global Headquarters
- Rooftop Cinema Club
- Ed Debevic’s
- Promontory Point
- Second City Comedy Club
- Gangsters & Ghosts Walking Tour
Millennium Park
See the world-famous Cloud Gate sculpture, affectionately nicknamed “The Bean”, at Millennium Park. You can also splash in the Crown Fountain, enjoy an outdoor concert in the summer, and go ice skating in the winter.
Wrigley Field
Wrigley Field is an iconic landmark. It has been the home of the Chicago Cubs since 1916 and is the second-oldest major league ballpark in the United States. Enjoy America’s favorite pastime and order a Chicago-style hot dog while cheering on the Cubs!
Architecture Boat Tour
One of the best ways to experience Chicago and learn about its fascinating history is on an Architecture Boat Tour. The Chicago River cuts through the center of the city, and a boat cruise offers a unique view of the skyline. You’ll pass by iconic historic landmarks while listening to informational and entertaining commentary.
Chicago Riverwalk
In addition to a river cruise, you can also walk and take in the views along the 1.25-mile waterfront path that winds along the Chicago River through the heart of the city.
North Avenue Beach
Relax, swim, play, and enjoy the views at Lake Michigan’s most popular urban beach. This beach is located in Lincoln Park and is free to visit. It features a long stretch of sandy beach, volleyball courts, and kayak and jet ski rentals.
Navy Pier
Navy Pier is one of Chicago’s premier tourist attractions. It features the Centennial Wheel, the Chicago Children’s Museum, Pier Park, the Chicago Shakespeare Theater, the Flyover Chicago flight simulation ride, and a handful of waterfront restaurants and shops. You can even take a thrilling speedboat ride around Lake Michigan!
Shedd Aquarium
Visit the 5-million-gallon aquarium with over 32,000 aquatic animals. It is considered one of the oldest non-governmental aquariums in the US and offers unique animal encounters and immersive experiences. The Wild Reef is one of our favorite exhibits where you can observe sharks.
Lincoln Park
Lincoln Park is one of the most popular neighborhoods in Chicago. The park itself is home to the free Lincoln Park Zoo, the Conservatory & Gardens, the Nature Boardwalk, the Alfred Caldwell Lily Pool, the photogenic Honeycomb Pavilion, the Endangered Species Carousel, the Nature Museum, and North Avenue Beach.
Magnificent Mile
This one-mile stretch of North Michigan Avenue is lined with luxury shops, restaurants, and upscale hotels. It is Chicago’s version of Fifth Avenue in New York City. Our kids love the Harry Potter Shop and the American Girl Store, which are both located here.
Willis Tower Skydeck
Take in the panoramic views of Chicago from “The Ledge” glass observation box 103 stories above the city. The best time to visit is at sunset when the sky is glowing, and the city lights begin turning on. There is also an interactive museum where you can learn about the history of Chicago.
Chicago Deep Dish Pizza
You can’t come to Chicago and NOT eat a slice of legendary Chicago deep-dish pizza. This pizza is unique because the cheese and toppings are on the bottom, and the sauce is on the top. Pequod’s and Girodono’s are arguably the best places in the city to get a thick slice of Chicago deep-dish pizza. Each pizza is cooked to order and takes some time, so be patient. It will be worth the wait!
Chicago “L” Train
Chicago’s unique elevated train line, referred to as the Chicago “L”, has become an iconic fixture in Chicago’s cityscape. Service first began in 1892, and the trains have now been rumbling above the city streets for over a century. Hop on board and take in the sights from the famous Downtown Loop that was completed in 1897.
Field Museum
This world-renowned natural history museum was always my favorite place to visit when I was younger, and my kids loved it as well. The massive T. rex skeleton and Titanosaur Maximo are a big draw, as well as the mummies exhibit.
Chicago Theater
Watch a performance in the Theater District and snap a photo of the iconic six-story high Chicago Theater marquee. The Chicago Theater first opened in 1921, and its lavish interior earned it the nickname, the “Wonder Theater of the World”.
Grant Park
Grant Park is lovingly referred to as “Chicago’s front lawn”. This sprawling green space is perfect for a summer picnic and also hosts festivals and events throughout the year. The Maggie Daley Park is located in the northeastern portion of Grant Park and has an awesome playground, rock climbing walls, a children’s play garden, mini-golf, and an ice skating path in the winter.
Lakefront Trail
One of our favorite things to do in the city is rent a bike and ride along this beautiful 18-mile paved urban trail. The trail follows along the shore of Lake Michigan and boasts awesome city and lake views. It also connects to popular beaches, parks, and attractions, including Lincoln Park, North Avenue Beach, Shedd Aquarium, Field Museum, and Navy Pier. There are several cafes and concession stands along the trail as well.
Chinatown
If you’re craving a steaming bowl of authentic noodles, head to Chinatown! This vibrant neighborhood moved to its current location in 1912 and is anchored by the iconic Chinatown Gate. Some of the best restaurants include MCCB Restaurant and QXY Dumplings.
Garrett’s Popcorn
Garrett’s Popcorn has become a Chicago institution. Female entrepreneur, Gladys Otto Garrett, opened the first small-batch popcorn shop in Chicago in 1949. Its signature “Garrett Mix” combination with cheese corn and caramel corn was introduced in the 1970s and has been one of Chicago’s most beloved snacks ever since!
Adler Planetarium
Learn about the universe at America’s first planetarium! Adler Planeterium features interactive exhibits, historic artifacts, immersive experiences, and dome theaters for digital sky shows. You can also view planets from Chicago’s largest public telescope at the Doane Observatory.
McDonald’s Global Headquarters
This is unlike any McDonald’s you’ve ever been to before! It features a rotating menu with international dishes from around the world, like the Teriyaki Chicken Sandwich from Japan, Sweet Potato Fries from Costa Rica, McPizza Bites from Italy, Biscoff McFlurry from Belgium, Salted Caramel Dipped Cone from South Korea, and the Big Tasty Mushroom Burger from Saudi Arabia.
Rooftop Cinema Club
Enjoy a summer movie under the stars at the Rooftop Cinema Club. This outdoor theater is located on the rooftop of Fulton Market with great views of the twinkling city skyline. The theater features comfortable seating, wireless headphones for sound, and food & drink concessions.
Ed Debevic’s
Ed Debevic’s is Chicago’s most famous retro-themed diner. The original diner first opened in 1984, and it has since expanded to include locations around the US and even Japan. The menu consists of classic diner food like burgers, fries, and shakes. But the real draw is the snarky waitstaff who dish out witty remarks and climb on the tables to sing and dance. It’s quite the experience!
Promontory Point
Have a summer barbecue and roast s’mores on the firepits at the scenic Burnham Park on Promontory Point. This man-made peninsula juts out onto Lake Michigan and offers panoramic views of the Chicago skyline. It’s one of our favorite places to watch the sunset!
Second City Comedy Club
Second City is one of the top improv comedy clubs and schools in the world. It first opened in 1959 and is where many of the top comedians first got their start, including Chris Farley, Tina Fey, Amy Poehler, John Belushi, Bill Murray, Mike Myers, and many more. Make sure you book tickets for a show when you’re in Chicago!
Gangsters & Ghosts Walking Tour
Learn about Chicago’s fascinating dark history on this Gangsters & Ghosts Walking Tour. The tour takes you through the Chicago Loop district, where you’ll hear stories about notorious crimes, visit haunted locations, and learn how Al Capone and the mob shaped Chicago’s history.
I hope this list helps inspire you as you plan your trip to Chicago!
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