Things to Do in Chicago: 72 Hour Guide

With 72 hours in Chicago, you can dive deep into the city’s top historic attractions, restaurants, shopping areas, and a lot more in the downtown core.

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If you’ve got 72 hours to spend in Chicago and are on the hunt for awesome things to do, then step right up. Home of the original Ferris Wheel — created for the 1893 Chicago World’s Fair — the city has been all about wowing visitors in a big way for a long time. Discover the attractions that rock and cool places to eat and stay during your trip to the Windy City.

Day 1: Downtown/The Loop

If you’re not into architecture so much, you just might do a 180 after a trip to Chicago, where hotels and office buildings cut eye-catching figures across the skyline and are just as awesome inside. Standout hotels in Chicago’s Loop/Downtown area include the Chicago Athletic Association, which pumps new life into an 1893 Venetian Gothic building, Virgin Hotels Chicago, the ultra-modern Radisson Blu Aqua, and the historic Palmer House Hilton.

Morning Agenda

Zip on over to Millennium Park to see “Cloud Gate,” a curving, shiny stainless steel sculpture, also called “the Bean.” Designed by British artist Anish Kapoor, it’s 66 feet long and more than 30 feet high, with a 12-foot-high arch in the center — plenty high to stand underneath and snap a selfie. On the park’s north and south sides, don’t miss the super-cool modern art works in the outdoor Boeing Galleries.

View from below of a opper, turquoise Lion statue outside of the Field Museum in Chicago, an impressive stone building on a sunny day.

How to Spend the Afternoon

Jam-packed with 24 million cool pieces of the past and from the planet, Chicago’s Field Museum has tons of awesome stuff to check out during an amazing afternoon. Don’t miss the two rooms and artifacts from a 5,000-year-old Egyptian tomb, 14 mummies from Egypt and Peru, a study of the Tsavo man-eating lions, and finds from a sunken 12th-century Chinese ship. Plus, the museum’s Grainger Hall of Gems is bling central with rare jewels and gold objects that will blow your mind.

Aerial view of the Chicago skyline at sunset shows iconic skyscrapers and buildings downtown and throughout the city.

Nightly Events

Zoom up to Skydeck on the 103rd floor of Willis Tower, where you can test your grit on the Ledge, a glass balcony that juts out about 4 feet, for thrilling views of the city. Have dinner at the Metropolitan Club’s Globe dining room, where you can scope out the Windy City from the 67th floor. It’s open to the public on weekends and serves modern American eats.

Day 2: The Magnificent Mile

The Magnificent Mile includes North Michigan Avenue and the area right around it. Here, you’ll find hotels like the Peninsula, LondonHouse, the InterContinental, the Park Hyatt, the Sofitel Chicago, and the Tremont.

Start Your Morning Exploring

Book it to DuSable Bridge (also known as the Michigan Avenue Bridge) and along North Michigan Avenue to get a load of some of the city’s most most-famous buildings, including the Wrigley Building, 333 North Michigan, 875 North Michigan Avenue (previously known as the John Hancock Center), and Tribune Tower. Treat yourself to a French breakfast at Pierrot Gourmet at the Peninsula or a sushi and smoothie brunch at NoMi Kitchen at the Park Hyatt.

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Afternoon Activities

Shop till you drop at North Michigan Avenue’s designer boutiques and major department stores. Marvel at Shedd Aquarium’s aquatic life, or learn to throw a curve ball and try on a championship ring replica at the Chicago Sports Museum.

Close up view of a sausage dish with white beans and chanterelles at the Purple Pig restaurant in Chicago.

Night Time Entertainment

Dig into dinner at the Purple Pig, a Michigan Avenue eatery with its own award-winning take on cheese and cured meats. If you’re craving no-frills eats, then chow down on Chicago-style hot dogs at Portillo’s or classic deep-dish pizza at Lou Malnati’s.

View of the red and white Centnnial Ferris wheel and cityscape at Chicago’s Navy Pier on a clear summer morning.

Day 3: River North/Streeterville

The hotels of River North/Streeterville include the Langham Chicago, which sits in a cool skyscraper designed by star architect Ludwig Mies van der Rohe, the Westin Chicago River North, and the trendy ACME Hotel.

Early Morning Events

Choose from a creative menu of pancakes, egg dishes, and more at Yolk on East Ohio Street for breakfast. Next, book it to Navy Pier and take a spin on the 196-foot-high Centennial Wheel.

An Afternoon in Chicago

Spend the afternoon at Streeterville’s Museum of Contemporary Art and eyeball attention-grabbing works by artists like Doris Salcedo, Olafur Eliasson, Louise Bourgeois, and Josef Albers, from the museum’s motherlode of more than 2,500 pieces. When you’re ready for a bite to eat, grab lunch at the museum’s bright, modern restaurant, Marisol, which serves seasonal Midwestern eats.

How to Spend Your Final Night in Chicago

When the sun goes down, book seats for an evening show at the top-rated Chicago Shakespeare Theater on Navy Pier. Besides the classic plays by the Bard, enjoy hit plays — including musicals — by major playwrights like Samuel Beckett and Jessica Swale.

What are some cool and exciting things you’ve checked out in Chicago? Tag Dollar Car Rental in your latest Instagram photos to show off!

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