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

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!

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.

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.

Bobby's Bike Hike is a great value - providing signature guided bicycle and food tours of Little Rock's Riverfront and Historic Neighborhood attractions, appropriate for a variety of ages and fitness levels. Bobby's Bike Hike tours Little Rock in style, with brand-new Schwinn Comfort bicycles, 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. Bobby's folks in the shop are friendly and helpful and we will take the time to teach you the ropes before sending you on your way. Tours include the Historic Neighborhoods Tour and Bobby's 'Tike' Hike for families with younger riders, and our 'Pork & Bourbon' Tour sampling local unique southern treats.

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.

Great place for water sports and biking.

Tall Ship Windy is Chicago's Official Tall Ship! Many sailing trips daily, May - Sept rain or shine! To see current schedule online, visit our website and click "buy tickets" We have a full service bar aboard This is a fun adventure, for all ages! Open May through September

Offering Architectural Cruises, covering the north and south branches of the Chicago River, Historical Lake and River, Cocktail Cocktail Cruises and Firework Cruise offered in the evening, all cruises are 90 minutes, and have complimentary Starbucks Coffee and soft drinks.

Wateriders is seasonally closed until April of 2019. As the pioneers of kayaking on the Chicago River, Wateriders has been hosting kayak tours for 21 years. Guests get an unbeatable view of the city's beautiful interior skyline as they paddle through the architectural canyon of downtown Chicago. Both guided tours and open rentals are available. Located on the riverwalk behind the East Bank Club in the River North neighborhood, Wateriders is ideally situated for making the most out of one's adventure, and is easily accessible by all means of transportation. Discounted garage parking available less than 2 blocks away,