The 10 Best Outdoor Activities in Downtown / The Loop, Illinois (IL)

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!

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.

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.

Capture Chicago's iconic locations with us! We will show you how to use your camera controls to get stunning photos of Chicago's best known areas. Select from Millennium Park Safaris, Bike Safaris, Night Safaris at Navy Pier, or Lincoln Park Zoo Safaris. And if you love photography and traveling, then consider joining us for a regional, national or international safari!

Just Sailing Ltd. exists to facilitate incredible sailing adventures on Lake Michigan. We loooove sailing. We love sailing because it is simultaneously exciting and relaxing. We love sailing because its fun when its warm and sunny, and its fun when its rainy and gray. We love sailing because it is the fastest way to get out of the city, into the quiet of the majestic Great Lakes. We love sailing because it allows us to feel the power of natural forces, and harness them with skill and intuition.

Sailboat charters in Chicago on Lake Michigan for up to 6 people.

Experience the other side of Lake Shore Drive We offer completely customized boat Charters and Rentals. We have multiple boats ranging from 37' to 50' in length. Cruises start at 1.5 hours for a wonderful skyline tour of Chicago.

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!