24 Hours In Chicago, Illinois - Updated 2022


Chicago is known as the Midwest’s cultural and commercial powerhouse. The city is teeming with rich art and culture. Of course, as a visitor in Chicago, you would want to experience it all. If you only have a single day in Chicago, then it is definitely not possible to take in everything that the city has to offer. However, you can still make use of the 24 hours in the city and try to hit all the record stores, art galleries and museums around the town. This article aims to handpick the best things you can do with 24 hours in the city. As such, continue reading and prepare for the ultimate day out in Chicago.

1. Big Bus Chicago Hop-On Hop-Off tour (from USD 44.0)

The Big Bus Chicago Hop-On Hop-Off tour shows you Chicago in a nutshell. Hop on this bus for panoramic top-deck views of iconic skyscrapers in the city, as well as Lake Michigan. If you wish, hop off the bus to explore famous attractions like Magnificent Mile, Field Museum and Adler Planetarium. Flexible sightseeing in the Windy City is a breeze with Big Bus Chicago. This tour has 14 stops, with the flexibility to spend as much time as one wants in any of the stops. There is live commentary on board allowing visitors to get an insight into the city’s colorful history. The full circuit takes about two hours, but because visitors can hop off and back on as many times as they want, they can easily spend a day exploring the city’s sights this way.

Chicago Hop-On Hop-Off Big Bus Tour

Duration: 2 hours

1062 reviews

2. Bobby's Bike Hike Chicago (from USD 54.99)

24 hours in chicago | bobby's bike hike chicago

This is a three-hour bike tour which takes visitors around the lakefront neighborhoods. This is a guided bicycle excursion in which visitors will be able to see several parks and beaches as well. This tour is appropriate for a variety of ages, interests, and fitness abilities. Get the chance to see the Gold Coast mansions, Lincoln Park Zoo and the charming Old Town Historic District. Bikes and helmets are provided and you can make use of the city’s bike paths. Visitors are reminded to wear comfortable clothing during this tour.

Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

Duration: 3 hour

25 reviews

3. Spirit of Chicago Sunset Dinner Cruise (from USD 122.0)

Enjoy the sea breeze and a tour of Chicago during sunset with this tour. Through the Spirit of Chicago Sunset Dinner Cruise, guests get a three-hour sunset cruise experience, sightseeing and dancing along the shores of Lake Michigan. Savor incredible views as you sail past the Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field. During the course of the trip, visitors also get to enjoy a sumptuous buffet. A live DJ is on standby, who will play a selection of dance favorites. This cruise begins at the city’s Navy Pier in the evening. Guests can also enjoy a few drinks at their own cost. During the summer months, guests can upgrade their sunset dinner cruise to a fireworks dinner cruise. Guests can enjoy a spectacular fireworks display on Wednesdays and Saturdays.

Chicago Signature Dinner Cruise on Lake Michigan

Duration: 3 hours

161 reviews

4. Gangsters and Ghosts tour in Chicago (from USD 35.0)

Try out something different while in Chicago and experience this Gangster and Ghosts tour. This is a fun and informative experience which is best suited for adults. Your guide is a historian and he will take you through the Chicago Loop which was once a hub for bootleggers, speakeasies and infamous gangsters. Get the chance to visit gangster hangouts as well as haunted sites like Palmer House, Congress Hotel and Death Alley. Visiting these places will give guests an insight into Chicago’s dark and eerie areas. Listen to ghost stories from your guide and check out what used to be secret underground tunnels used by bootleggers. Do remember to bring along a camera so that memories can be captured. The total tour lasts for two to two and a half hours, and it is a walking tour through the city’s downtown district.

Gangsters and Ghosts Tour in Chicago

Duration: 2 hours

2708 reviews

5. Chicago Tastes of Chinatown Walking Food tour (from USD 74.0)

Fancy a gastronomical experience? Spend some time in this city exploring the food scene in Chicago’s Chinatown. This tour lasts for about three hours and it’s a guided walking tour. Explore the various cuisines originating from various parts of China and learn how the Chinese culture has greatly influenced Chicago. Enjoy tastings from restaurants and other food venues in Chinatown, giving you a sample of the kinds of Chinese cuisines served. The tour starts at the Chinatown gate in Chicago and it begins with a sampling of dumplings. Next, visitors get to sample food from the Xi'an region, with the opportunity to stop by markets and souvenir shops. Also, get the chance to try Beijing-style duck, Szechuan hot pot and a custard tart from the oldest bakery. This is a memorable tour for those interested in the Chinese food scene in Chicago.

Chicago's Chinatown Food and Walking Tour

Duration: 3 hours

78 reviews

6. Chicago Skydeck Experience Ticket (from USD 36.0)

chicago skydeck experience ticket

This is a two-hour tour which provides visitors with an exhilarating experience and a great time. One can enjoy the views of the whole of Chicago from the top of the Willis Tower. In order to reach the top, one will need to ride 103 floors to the Skydeck and step out onto The Ledge. The Ledge is a glass-paneled box with vertical views to the ground below. Through this experience, visitors also get the chance to learn about Chicago’s rich cultural history with museum-quality exhibits. Visitors also get the chance to watch a movie which explains the history of the Willis Tower as well as other architectural wonders of Chicago.

Travel tip by Chicago Local Expert - John
Posted on: Feb 19, 2021

With just 24 hours in Chicago, going up to the Skydeck is a great choice as long as the weather is clear. With some of the best views of the city, walk out onto the glass and grab a selfie or post an Instagram/Snapchat story to document your trip! Make sure to book your ticket online in advance and select a time slot for when the weather is predicted to be best.

Chicago: Willis Tower Skydeck and The Ledge Ticket

1872 reviews

7. Art Institute of Chicago (from USD 35.0)

Book the fast pass for a visit to the Art Institute, known as Chicago’s world-class art museum. It is also the second-largest museum in the United States. The museum is located in Grant Park and it features a wide range of impressionist, post-impressionist, modern and contemporary works. If you are interested in the arts scene in Chicago, then this one is a must-see place in the city. Works by Pollack, van Gogh, Renoir, Monet and Picasso are all featured. Skip long lines at the General Admission lines and gain priority access to the galleries and special exhibitions. Complimentary tours are available daily at noon, and guests under 14 years enter for free. This museum is also family friendly as there are some kid-friendly art activities that take place in a separate section of the museum.

Art Institute of Chicago Fast Pass Admission in Grant Park

Duration: 3 hours

48 reviews

8. Helicopter Night Flight Experience (from USD 145.0)

helicopter night flight experience

Explore Chicago by night in the air. Take this splendid helicopter flight above Chicago after dark and get a good view of the sights in the city. Get the chance to browse the exhibits that explain the history of this destination. Also get the opportunity to grab the controls on a flight simulator and maneuver through a virtual landscape as you take off. After all the safety checks are done, your helicopter will ascend into the night sky and the pilot will ensure you get unobstructed views of the landmarks in the city. Fly over McCormick Place and Lake Shore Drive and finally over the azure waters of Lake Michigan. As you explore the city from the air, your pilot will provide you with a live commentary. This tour makes for an ideal romantic evening out.

Chicago: City Lights Helicopter Experience

Duration: 15 minute

36 reviews

9. Chicago Architecture Walking Tour: Historical Masterpieces of the Loop (from USD 30.0)

This is a two-hour walking tour which will allow visitors to experience Chicago’s architectural history and highlights. With a knowledgeable guide, visitors get the opportunity to tour through Loop District. During this tour, enjoy the bustling streets of the diverse city and stand in awe of the beautiful architecture. This walking tour will prove to be memorable for visitors who will go home with tons of memories. There are three separate tour routes. Each one takes visitors through different parts of Chicago. As you explore this fascinating destination, unravel some of the hidden gems of the city in the beautiful alleys and back alleys.

Chicago, the Loop: Guided 2-Hour Architecture Walking Tour

Duration: 2 hours

25 reviews

10. Chicago Tickets (formerly John Hancock Observatory) (from USD 30.0)

chicago tickets (formerly john hancock observatory)

Get a panoramic view of the beautiful city of Chicago by booking a 360 Chicago tour. This 90-minute tour allows visitors to enjoy the best views of the city. The 360 Chicago, which was formerly known as the John Hancock Observatory, rises to a spectacular height of 94 stories. One would be able to take pictures of beautiful lakes as well as the Windy City itself. Get superior lake views with close-up vistas of Chicago’s amazing skyscrapers. Guests can select their preferred date of visit and book the tickets online.

Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

496 reviews

Chicago in 24 hours

In 24 hours, there is so much to do and see in Chicago. Take a look at the varied options for tours that are offered in the city, and make your bookings. Go ahead and enjoy Chicago with whatever time you have.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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I'm a mother to 2 wonderful young kids and enjoy travelling with my family. Having travelled to many countries across the world, I am particularly keen on trying out new cuisine and sightseeing...Read more

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