10 Things To Do This Weekend In Chicago - Updated 2022


Chicago is among the most populous cities in the United States. It is the most visited city as it is a home to many tourist sites and educational institutions. Being the birthplace of the sky scrapper, Chicago boasts unique architecture of all centuries. Enjoy the Chicago skyline both at night and at dawn, and cruises on Lake Michigan and also the Chicago River. Get to find out the story behind Chicago’s public art and the monuments available. Mingle with the Chicagoans, learn their great accents and culture. The theater performances including comedy shows, kids shows, adult movies and also live performances are among the fun activities the city has to offer. Music festivals like the Chicago Blues and Chicago Jazz take place at different times of the year. Visit this city with your loved ones and enjoy the luxuries that come with it. To get you started as you plan your visit, here is a list of the things to do in Chicago this weekend.

1. Chicago architecture river cruise (from USD 46.0)

Cruise along the Chicago River as you get the history of the city from the tour guides. Discover how Chicago grew from a small settlement to being the big city it is now. You can take pictures of buildings or yourself, as the tour has several pauses. The boat is big enough to carry around 250 passengers and features open-air decks, full-service bars, and granite restrooms. This will be an experience you’ll never forget.

Chicago Architecture River Cruise Guided Tour

Duration: 1 hour 15 minutes

8182 reviews

2. Tastes of Chicago bike tour (from USD 89.0)

Combine a bike tour of downtown Chicago with the city’s most popular culinary pleasures on this 4-hour excursion. It is a 13 miles (20.9 km) tour across Wrigley Ville, the Gold Coast, Old Town, Lakeview and Lincoln Park. The tour is guided by a local guide who will explain the food traditions and history of the towns you’ll go through. Along the way, you’ll stop at the bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.

Chicago Food Tour by Bike with Pizza, Beer, Hot Dogs, Cupcakes

Duration: 4 hours

369 reviews

3. Chicago Lakefront neighborhoods bicycle tour (from USD 54.0)

This is a 3-hour bicycle tour of Chicago’s Lakefront neighborhood. Guests are given a bicycle and helmet, then set out for a drive with a tour guide. The tour goes through elegant homes, Rush Street, Magnificent Mile, and along popular shores of Lake Michigan. The guide will add interesting facts about the neighborhood and the Chicagoans. It is appropriate for guests of all ages.

Bike Tour of Chicago's Lakefront Neighborhoods

Duration: 3 hours

162 reviews

4. Chicago walking tour (from USD 30.0)

You can enjoy Chicago’s architecture by walking around the city for two hours with a certified guide. This walk takes you through the most important period buildings and their critical role in the development of the movement’s signature style. During the course of your walk, you’ll stop to admire a range of exteriors and interiors that define the architectural golden age of the art deco and modern art movements. You will get to learn a lot more than you knew from the internet.

Chicago Walking Tour: Art Deco Skyscrapers Loop

Duration: 1 hour 30 minutes

88 reviews

5. Blue-man group (from USD 56.0)

Blue man group is a popular theatrical show in Chicago. Enjoy their performance at the Briar Street Theater. It is a group perfect for all ages (5+), languages, and cultures. It is one of the city’s longest-running theater shows, updated with a fresh take on today’s technological age. Children will enjoy the mixture of colors and light while adults will love the comedy. Get tickets at the theatre and prepare yourself for an unforgettable experience.

Blue Man Group at the Briar Street Theater in Chicago

Duration: 1 hour 40 minutes

103 reviews

6. Lake Michigan speedboat ride (from USD 34.0)

Have fun in the water by taking a thrilling boat ride tour from Navy Pier. This 30-minute, fast-paced speedboat ride is sure to get your heart racing, with a little history, humor, and information thrown in good measure. You will pass through famous attractions like Willis Tower, Grant Park, and Buckingham Fountain. Cruise back as you enjoy the city’s skyline and views of the landmarks.

30 Minute Lake Michigan Speedboat Ride

Duration: 30 minutes

147 reviews

7. Chicago observation deck (from USD 30.0)

This observatory brings you 1000feet to view the city skyline and also the neighboring states of Chicago. Early risers will be able to view the city from 9.00 am and those who enjoy the evenings have until 10.00 pm. It is a building of 94 floors but is accessed by the fastest lift in North America. This observatory features a tilt (a section of the windows are built to tilt outwards), an architect’s corner café, full bar cocktails, and an interactive technology in seven languages.

360 Chicago Observation Deck Admission Ticket

Duration: 1 to 4 hours

312 reviews

8. Historic Chicago walking bar tour (from USD 39.0)

This short walk allows plenty of time to see Chicago’s famous architecture and pubs on this tour. You will be taken through several pubs, historic buildings, and architecture by an expert guide. Facts about jazz history, social clubs, and prohibition era will be shared by the guide. Have fun socializing and knowing your group through games, nightlife, and other entertainment forms.

Chicago Historic Bar Walking Tour and Educational Pub Crawl

Duration: 2 hours 30 minutes

30 reviews

9. Special Ops Escape Room in Chicago (from USD 40.0)

In the River North area of downtown Chicago, there is an escape house that gives you a 60-minute escape experience. A game called game reality is played in which guests battle against time to solve puzzles, overcome challenges and defeat their doubts. According to your abilities, you and your group will be tested and work together to complete the task.

Special Ops: Mysterious Market Escape Room

Duration: 1 hour 15 minutes

10. Chicago prohibition tour (from USD 55.0)

The prohibition era was a colorful time in Chicago with gangs and mobs running plenty of speakeasies where liquor flowed. This tour takes you to four bars and pubs that defied the alcohol ban. You will learn about Chicago’s crime of the 1920’s; crime scenes and murder stories will also be told. Guests will be able to purchase recommended 1920’s cocktails and signature drinks. You will be taken around the four bars by a coach and a designated driver because the bars are tough to find.

Chicago Adults-Only Historic Bar and Speakeasy Tour

Duration: 3 hours 30 minutes

10 reviews

Enjoy a unique weekend in Chicago!

We hope this list has inspired your weekend plans. Whether you’re visiting or a resident looking for something new, we’re certain you’ll enjoy all these activities this weekend. Book these popular tours early, to avoid disappointment and have a fantastic weekend ahead!

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

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