10 Outdoor Activities in Chicago That You Shouldn't Miss

November 28, 2021 Vivienne Hutton

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. Chicago Architecture Center

Excellent
85%
Good
12%
Satisfactory
1%
Poor
1%
Terrible
1%
Overall Ratings

5.0 based on 2,708 reviews

Chicago Architecture Center

The Chicago Architecture Center (CAC), formerly the Chicago Architecture Foundation, is a nonprofit cultural organization with tours, exhibitions, programs and events for all ages. Visit the CAC on Wacker Dr. to view our 4,000-building scale model of Chicago, shop in our award-winning store or participate in a fun LEGO® building event in our ArcelorMittal Design Studio. Choose from 85 tours by boat, walking, bus, or even L train, including the CAFC River Cruise aboard Chicago's First Lady Cruises. Tours depart daily and are led by CAC's expert docent guides. Every October, check out CAC's free annual Open House Chicago festival. Proceeds from CAC’s tours and gift shop, as well as grants, sponsorships and donations, support this educational mission.

2. City Running Tours-Chicago

Excellent
97%
Good
3%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 241 reviews

City Running Tours-Chicago

Our PERSONALIZED RUNNING TOURS are completely customizable to the day, time, distance and sights you want to see. Your personal running guide will pick you up from where you are staying, run at your pace, provide water and have a camera in case you feel like capturing the moment. At the completion of the run we will return you to where you are staying and you walk away with a souvenir goody bag.

3. Urban Kayaks

Excellent
81%
Good
16%
Satisfactory
1%
Poor
0%
Terrible
2%
Overall Ratings

5.0 based on 487 reviews

Urban Kayaks

Kayak Tours, Rentals, and Lessons on the Chicago River. Located on the Chicago Riverwalk. Enter Riverwalk at Columbus and Wacker. The second location on the lakefront at Monroe Harbor.

4. Shoreline Sightseeing

Excellent
83%
Good
14%
Satisfactory
2%
Poor
1%
Terrible
0%
Overall Ratings

5.0 based on 5,434 reviews

Shoreline Sightseeing

TripAdvisor ranked Shoreline Sightseeing as the #1 Most Booked Tour in America! Shoreline Sightseeing is Chicago's leader in river and lake cruises! Featuring state-of-the-art tour boats and expert guides, Shoreline presents the Chicago skyline as you've never seen it before. With so many options among our lake and river cruises, we're sure to offer a tour your whole group will love. Our famous Architecture River Tours are led by knowledgeable and entertaining guides showcasing the city's rich architectural heritage. We also offer skyline lake tours, romantic sunset tours, and exciting fireworks cruises from which to see dazzling displays throughout the summer. Themed offerings include wine tasting cruises, brew cruises, 4th of July options, and St. Patrick's Day cruises. So set sail with Shoreline today, where every day is a celebration of Chicago!

5. Bobby's Bike Hike Chicago

Excellent
93%
Good
6%
Satisfactory
1%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 3,553 reviews

Bobby's Bike Hike Chicago

Bobby's Bike Hike Chicago is a great value - providing signature guided bicycle tours, year-round walking tours, and delicious food and culture tours. We have various tours designed for a wide variety of interests, ages, and skill levels. Check out our brand-new, season walking & food tours(Bobby's Hikes). Bobby tours Chicago in style with deluxe Schwinn Comfort bikes complete with cushy seats, fat tires, and annoying bells :). Our hand-selected guides are chock full of historical information which is sure to inform and entertain you on your journey. Our folks in the shop are friendly and helpful and they will take the time to teach you the ropes before sending you on your way. Tours include the Lakefront Neighborhoods Tour which was Voted Best Chicago Tour seven years in a row, the City Lights at Night Tour which is a healthy way to explore Chicago at night, Bobby's 'Tike' Hike for families with younger riders, and the Bikes, Bites, & Brews Tour which is a food sampling tour. If you want to learn about Chicago's seedier past, check out the Southside Chicago Gangster Tour. If you want the best views in Chicago, check out our brand-new Museums & Parks at Sunset Tour. We also offer year-round walking and food tours, including the Chicago Favorites Food Tour, Public Art & Architecture Tour, and the Holiday Hike - Season Sampling Tour. All walking tours make use of Chicago's elaborately unique indoor pedway system in inclement weather.

6. Free Tours by Foot

Excellent
89%
Good
10%
Satisfactory
1%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 1,201 reviews

Free Tours by Foot

Free Tours by Foot offers pay-what-you-like tours of Chicago, focusing on walking tour, self-guided bike tours and ghosts tours. Name your own price, including free. Pay-what-you-like tours are tours for every budget.

7. Chicago’s First Lady Cruises

Excellent
87%
Good
11%
Satisfactory
2%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 5,221 reviews

Chicago’s First Lady Cruises

Only the Chicago Architecture Center and Chicago's First Lady Cruises can showcase Chicago's world renowned city architecture with style, class and comfort on the official Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady. Open-air and air-conditioned seating is available. Learn about the architecture and design of over 50 buildings as described by CAC-certified volunteer docents/guides on this 90-minute tour that showcases all three branches of the Chicago River. Full-service bar aboard each vessel. All tours depart from the Chicago Riverwalk at Michigan Ave. and Wacker Dr. (southeast corner of the Michigan Avenue Bridge). Look for our blue awning.

8. Chicago River Boat Architecture Tours

Excellent
89%
Good
8%
Satisfactory
3%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 440 reviews

Chicago River Boat Architecture Tours

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river.

9. Tours and Boats

Excellent
94%
Good
5%
Satisfactory
1%
Poor
1%
Terrible
0%
Overall Ratings

5.0 based on 131 reviews

Tours and Boats

We've partnered up with some of the city's best, non-droning guides to offer fun and informed boat tours. These Windy City experts usher groups of travelers to myriad landmarks while sharing anecdotes that paint a vibrant picture of the city's history. During the company's sightseeing river tours, their boat float by well-known structures while travelers learn about the city's famed architecture.

10. See it All Chicago Tours

Excellent
85%
Good
11%
Satisfactory
3%
Poor
1%
Terrible
0%
Overall Ratings

5.0 based on 512 reviews

See it All Chicago Tours

UPDATE: FOR MAXIMUM SAFETY AT THIS TIME, PLEASE CONSIDER OUR NEW PRIVATE TOUR. JUST YOU AND YOUR FAMILY AND FRIENDS. TEMPORARY LOW PRICE! See it ALL Chicago tours invites you to join us on one of our award winning Chicago mini bus tours. See Chicago in luxury, as you ride in one of our large windowed, climate controlled mini buses. Fun and informative guides, stops at several picturesque areas and the ability to ask your guide questions at any time make this a very popular tour. You will not only see the downtown sights, but also visit several interesting neighborhoods, including The Gold Coast and Lincoln Park. Three photo stops make this a tour that is not to be missed! Pickups and drop offs are available from most downtown hotels for the Mini Bus Tour. If you are going on the combination Mini Bus and Chicago River Architecture tour, the tour will conclude at the boat dock at Michigan Ave. and Wacker Drive. Almost all downtown hotels are within one mile of that location.

ThingsTodoPost © 2018 - 2024 All rights reserved.