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How To Spend 24 Hours in Chicago

June 19, 2023

Are you trying to figure out what to do with 24 hours in Chicago, Illinois? There are so many fun things to do in downtown Chicago that it can be tough to decide. You could hit up Oak Street for a lavish, upscale shopping spree. Or visit the historic Robie House, located in Hyde Park. Or maybe grab the "Best Burger in Chicago" at Ditka's Restaurant on Chestnut Street. The opportunities for excitement are endless, so here's a narrowed-down list of what to do. Downtown Chicago's best day-long itinerary begins now.

Kick Off Your Day With Breakfast and Sightseeing

Undoubtedly, eating a hearty breakfast can be one of the best ways to jump-start your day. So, it's clear that the first thing you should do while visiting Chicago is grab a yummy breakfast before sightseeing.

One popular spot is Batter & Berries in Lincoln Park. This cafe offers made-from-scratch breakfast food items. The restaurant is well known around town for its French toast flights, which come with blueberry, lemon, caramel, and strawberry flavors.

If you want organic or vegan options, try M. Henry in Edgewater for the Vegan Epiphany made with organic tofu, sautéed sweet onions, and rapini. Once you're fueled up, explore what to do in downtown Chicago next.

Dive Into Art and History

Chicago has a rich history as a melting pot of cultures, and you can witness some of that legacy at the Art Institute and in nearby Grant Park. If you're visiting Chicago solo, a stop at Grant Park is also one of the best things to do in Chicago alone.

Explore the Art Institute of Chicago

See one of the largest museums in America, the Art Institute of Chicago, at 111. S Michigan Ave. Located in downtown Chicago, it’s one of America's oldest and grandest museums. The Art Institute of Chicago houses over 300,000 pieces. Within its walls, you'll see famous works by legendary artists such as Claude Monet, Vincent van Gogh, Grant Wood, and Pablo Picasso.

Stroll Through Grant Park's Serene Green Spaces

Grant Park, often called "Chicago's Front Yard," is over 300 acres of beautiful public park area in the Loop. The park was named after President Ulysses S. Grant in 1901. Here, you can enjoy the lakefront views and visit other attractions as well.

You can walk through Millennium Park and take selfies with the iconic "Bean." After that, head over to Maggie Daley Park, where you can jump into some recreational sports thanks to a climbing wall, a miniature golf course, and even a seasonal ice-skating rink. Next, you can venture to the southeastern part of Grant Park to check out the Field Museum, Shedd Aquarium, or Adler Planetarium. Be sure to stroll around the lovely Grant Park Rose Gardens before you leave.

Enjoy State-of-the-Art Tour Boats

Public transportation in Chicago includes water taxis, but you can also discover fun guided boat tours. If you want to catch a glimpse of the exquisite architecture that the Windy City is known for, take a ride on the Shoreline Sightseeing Architectural River Tour. You can start the tour from two different docks, Michigan Avenue or Navy Pier.

You'll be led by a professional guide who will educate you about many Chicago sights, all from a unique vantage point on the water. While floating down the Chicago River, you'll see sights like the Wrigley Building and the Tribune Tower. The tour lasts up to 75 minutes, and you'll see over 40 of the city's iconic buildings and landmarks, including the historic Chicago Water Tower.

Witness Breathtaking Views

You can catch amazing views of the skyline in Chicago from two different locations: the 360 CHICAGO observation deck and Skydeck Chicago.

360 CHICAGO Observation Deck

If you go to 360 CHICAGO at the former John Hancock Center on Michigan Avenue, you can see the city from over 1,000 feet in the air. TILT is a first-of-its-kind platform that "tilts" you out over the city. You can also grab a local drink at the CloudBar and see interactive exhibits about the history and architecture of Chicago while you're at the top.

Skydeck Chicago

You must see the tallest building in Chicago, the Willis Tower. The Willis Tower, formerly the Sears Tower, sits 110 stories tall. You can go to the 103rd floor and catch some of the city's most breathtaking views (not to mention a couple of surrounding states) from Skydeck, one of America's highest observation decks. The Ledge is made of transparent glass, if you're brave and want an even better view.

Savor Chicago's Culinary Delights and Catch a Show

It's hard to top that vista, but dinner and a show might come close. Mosey on over to the eclectic neighborhood of Wicker Park, and you can find many unique places to eat. Big Star offers Mexican cuisine and has some of the best tacos in the area. They offer quality bourbon, classic rock music, and an open patio outside. If you are more interested in juicy hamburgers, stop at Small Cheval. Small Cheval is a retro hamburger-and-fries joint with a casual patio where you can sit and enjoy your meal.

You can also choose one of the more upscale restaurants that Wicker Park offers. Schwa offers a special, multi-course meal, but be sure to make a reservation. After dinner, catch a show at The Den Theatre or Broken Nose Theatre, which bring theater to everyone with pay-what-you-can admission fees.

Conclude With a Vibrant Nightlife Experience

Now, what to do in Chicago at night? Chicago has an active nightlife scene. From dance clubs on rooftops to cocktail bars and nightclubs all over the city, you can find something fun to do to wrap up the perfect day in Chicago.

First, visit The Underground in River North, which has a 1920s speakeasy vibe. Then, go to Lincoln Park, play some old-school arcade games, and grab a beer at Replay Lincoln Park.

Plan Your Next Unforgettable Chicago Adventure

Now that you have a sense of the fun you can have in Chicago, it's time to talk about your next trip. Chicago CityPASS® tickets grant you discounted admission to some of Chicago’s most popular things to do.

Chicago Lodging

To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you:

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