
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
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.
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
Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop is a guided outdoor experience based in Chicago, Illinois that keeps the…
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
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…