Things to do in Chicago, Illinois (IL): The Best Outdoor Activities

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.

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!

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.

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.

Join us for a 2 hour private Chicago sailing charter, for groups of 2-6, departing from Burnham Harbor 5 times per day, 7 days per week. Please visit our website, call, text, or email and BOOK a Chicago sailing tour today! https://saltydogchicago.com.

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.

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.

Chicago Running Tours & More offers scheduled and private tours. Our scheduled tours are at or just over the 5k distance and range from 90 minutes to 2 hours. Our guides have been trained by a "certified" Chicago Professional Tour Guide. Join us for a morning SCHEDULED run: Grant Park 5k at 8 a.M. Sundays & 7:15 a.M. Thursdays. Chicago River Navy Pier 5k at 7:15 a.M. Tuesdays and Fridays. Chicago Tragic Events at 8 a.M. Saturdays and 7:15 a.M. Sundays. We have a limit of 15 participants for our scheduled runs. Our PRIVATE tours include 1) City in a Garden (5.62 Miles), 2) Tower to Tower (6 miles), 3) Run to Wrigley (6.48 Miles), 4) Devil in the White City (8.1 Miles) Participants who complete all 4 private routes receive a 26.2 Finishers certificate and a long sleeve tech finishers shirt. Come join us for the best tour experience in Chicago while you take care of your cardio needs at the same time.

Climb aboard Chicago's largest sailing catamaran, Latitude Adjustment. 3rd Coast Charters offers private cruises and lessons for all ages and all occasions. You can enjoy your own exclusive experience with our catered Corporate Outings, Bachelor or Bachelorette parties and family gatherings utilizing our optional Yacht Concierge. From morning brunch to moonlight cruises and everything in-between, 3rd Coast Charters give you and your guests an experience that will last a lifetime. Make your special occasion memorable with one of our private cruises. Captain and crew promise a great day or evening out on the water plus concierge and catering options available to make it truly unforgettable!