
Chicago, Illinois
Chicago Architecture River Cruise
Cruise Chicago's harbor lasting 1 hour 15 minutes (approx.) with views of Chicago River from the water.
★ 4.8 (17010 reviews)
From $53.70
Chicago, Illinois
Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the scenery front and center. Expect a steady pace, local context, and a comfortable rhythm that lets you focus on the landscape.
Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop delivers a guided hiking experience with a relaxed Illinois, the route focuses on standout viewpoints and comfortable timing so you can enjoy the setting without feeling rushed.
We classify the skill level as All levels with steady footing, with the day structured around a flexible half-day window. Guides adapt the flow for the group, offering helpful context and optional pauses while keeping the outing smooth and approachable.
Scenery and local insight are the highlights. Expect thoughtful stops, clear guidance, and a route that balances exploration with comfort.
Affiliate disclosure: This booking link is an affiliate link. If you book, we may earn a commission at no extra cost to you.

Chicago, Illinois
Cruise Chicago's harbor lasting 1 hour 15 minutes (approx.) with views of Chicago River from the water.
★ 4.8 (17010 reviews)
From $53.70

Chicago, Illinois
Sail Chicago's bay lasting 2 hours (approx.) with views of Chicago River from the deck of a private or small-group yacht.
★ 4.7 (2440 reviews)
From $49

Chicago, Illinois
Sail Chicago's bay lasting 1 hour 30 minutes (approx.) with views of Chicago River from the deck of a private or small-group yacht.
★ 4.5 (1692 reviews)
From $45

Chicago, Illinois
Sail Chicago's bay lasting 1 hour (approx.) with views of Navy Pier from the deck of a private or small-group yacht.
★ 4.4 (951 reviews)
From $33

Chicago, Illinois
Sail Chicago's bay lasting 1 hour 30 minutes (approx.) with views of Navy Pier from the deck of a private or small-group yacht.
★ 4.8 (842 reviews)
From $55

Chicago, Illinois
Lift off over Chicago on a helicopter flight lasting 15 minutes (approx.) with aerial views of skyline and landmark rooftops.
★ 4.9 (412 reviews)
From $249

Chicago, Illinois
Lift off over Chicago on a helicopter flight lasting 15 minutes (approx.) with aerial views of skyline and landmark rooftops.
★ 4.9 (638 reviews)
From $189

Chicago, Illinois
Taste local specialties while exploring historic downtown around Loop District on a guided walking route.
★ 4.8 (367 reviews)
From $89

Chicago, Illinois
Taste local specialties while exploring historic downtown around River North on a guided walking route.
★ 5.0 (87 reviews)
From $299

Chicago, Illinois
Explore Chicago and Millennium Park on a guided route with well-placed stops for views and photos.
★ 5.0 (118 reviews)
From $245

Chicago, Illinois
Follow a curated route between hand-selected estate wineries such as Route Planning across Chicago's vineyard country.
★ 5.0 (76 reviews)
From $350

Chicago, Illinois
Explore Chicago and Chicago Pedway on a guided route with well-placed stops for views and photos.
★ 4.8 (441 reviews)
From $65

Chicago, Illinois
Cycle through Chicago, linking Millennium Park, on a guided bike route with neighborhood context and photo stops.
★ 4.9 (1189 reviews)
From $60

Chicago, Illinois
Cycle through Chicago, linking West Loop, on a guided bike route with neighborhood context and photo stops.
★ 4.9 (767 reviews)
From $75

Chicago, Illinois
Explore Chicago and Magnificent Mile on a guided route with well-placed stops for views and photos.
★ 5.0 (24 reviews)
From $425

Chicago, Illinois
Cruise Chicago's harbor lasting 2 hours 30 minutes (approx.) with views of Navy Pier from the water.
★ 4.6 (512 reviews)
From $180

Chicago, Illinois
Sail Chicago's bay lasting 2 hours (approx.) with views of Burnham Harbor from the deck of a private or small-group yacht.
★ 5.0 (54 reviews)
From $450

Chicago, Illinois
Explore Chicago and Biograph Theater on a guided route with well-placed stops for views and photos.
★ 4.6 (179 reviews)
From $42

Chicago, Illinois
Cycle through Chicago, linking Lincoln Park, on a guided bike route with neighborhood context and photo stops.
★ 4.9 (263 reviews)
From $55

Chicago, Illinois
Explore Chicago and Art Institute of Chicago on a guided route with well-placed stops for views and photos.
★ 4.7 (256 reviews)
From $45

Chicago, Illinois
Sail Chicago's bay lasting 1 hour 30 minutes (approx.) with views of Chicago River from the deck of a private or small-group yacht.
★ 4.9 (174 reviews)
From $89

Chicago, Illinois
Taste local specialties while exploring historic downtown around Chicago Loop on a guided walking route.
★ 4.9 (1012 reviews)
From $89
Chicago, Illinois
Spray Paint 'n' Sip- Chicago is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the scenery front and…
Chicago, Illinois
Art Institute of Chicago Skip-the-Line Tour (Semi-Private) is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple…
Chicago, Illinois
Art Institute of Chicago Skip-the-Line Tour (Private) is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and…
Chicago, Illinois
Private Luxury Yacht (12 Person Max) is a self-guided equipment rental in Chicago, Illinois. This equipment rental includes flexible duration options, clear pickup details, and rental terms so you can explore at your own pace.
Chicago, Illinois
The World Within (Part One): Dazzling Interiors™ of the Loop is a guided outdoor experience based in Chicago, Illinois that keeps the logistics…
Chicago, Illinois
Miami Beach Ultimate City Bike Tour is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the scenery front…
Chicago, Illinois
Captain Trooper Moores is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the scenery front and center.…
Chicago, Illinois
The Christmas Tree Crawl: The Magic of Chicago at the Holidays is a guided outdoor experience based in Chicago, Illinois that keeps the logistics…
Chicago, Illinois
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour is a guided outdoor experience based in Chicago, Illinois that keeps the…
Chicago, Illinois
All That Glam: Chicago’s Art Deco Masterpieces is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the…
Chicago, Illinois
Glow- A Neon Street Art Workshop is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the scenery front and…
Chicago, Illinois
Captain Nick Bieker is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the scenery front and center.…
Chicago, Illinois
Art Institute of Chicago Tour with Skip-the-Line Tickets (Semi Private) is a guided outdoor experience based in Chicago, Illinois that keeps the…
Chicago, Illinois
The World Within (Part Two): Secret Interiors of the Riverfront is a guided outdoor experience based in Chicago, Illinois that keeps the logistics…
Chicago, Illinois
Marvels & Masterpieces: An Engineer's Guide to Chicago Architecture is a guided outdoor experience based in Chicago, Illinois that keeps the…
Chicago, Illinois
Bikes, Bites & Brews: Chicago's Signature Dishes Bike Tour is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple…
Chicago, Illinois
Chicago in the Roaring '20s: Art Deco, Flappers, Gangsters, & Prohibition is a guided outdoor experience based in Chicago, Illinois that keeps the…
Chicago, Illinois
Captain Pat Erwin is a guided outdoor experience based in Chicago, Illinois that keeps the logistics simple and the scenery front and center. Expect…