Destinations
All tours (81–100 of 154)
Chicago: Adults-Only Ghost Tour & Haunted HistoryAdults-only ghost tour through Chicago's darkest history: Iroquois Theatre tragedy, haunted hotels, Al Capone's ghost. Local guide, 2+ hours, wheelchair accessible.
- 48 reviews
- 4.25★
- Duration
- 1h 30m
- Every day
- 20:30
Chicago: Willis Tower & Cloud Gate Half-Day Architecture TourHalf-day Chicago architecture tour covering Willis Tower, Marina City, Cloud Gate & Millennium Park. Small groups, expert guide, bottled water included. Starts 9am downtown.
- 46 reviews
- 4.96★
- Duration
- 2h 30m
- start times · Tue–Sun
- 2
Christmas Tree Crawl Chicago: Holiday Decorations TourWalk downtown Chicago's holiday decorations on a guided Christmas treasure hunt covering 1.5 miles of trees, traditions and little-known stops.
- 44 reviews
- 4.86★
- Duration
- 2h
- start times · Thu–Sun
- 2
Haunted Chicago Segway Tour: Ghosts & GangstersGlide past Chicago's most haunted sites and mob-run speakeasies on a 2-hour Segway tour with a certified guide: ghost stories, Al Capone's underworld.
- 38 reviews
- 4.71★
- Duration
- 2h
Lake Michigan Kayak & SUP Rental: Downtown Chicago at Ohio Street BeachKayak and paddleboard rentals at Ohio Street Beach near Navy Pier. Calm Lake Michigan waters, downtown skyline views, life jackets included. 1–2 hours, beginner-friendly.
- 26 reviews
- 4.81★
- Duration
- 1h–2h
Midway to Chicago: Private Luxury SUV Transfer CurbsidePrivate car service from Midway Airport to Chicago hotels and destinations. Licensed drivers, GPS tracking, 24/7 support, fixed pricing. 16+ years, 5x Excellence.
- 21 reviews
- 5.00★
Chicago O'Hare to Midway: Private Sedan Transfer & PickupPrivate sedan transfer between Chicago O'Hare and Midway airports or downtown hotels. Licensed drivers, $350K insurance, curbside pickup, 24/7 service. Fixed price.
- 21 reviews
- 5.00★
Chicago: 2-Hour Luxury Minibus Tour & Skyline ViewsTwo-hour guided minibus tour of Chicago's skyline, Grant Park, Cloud Gate and Lake Michigan views. Climate-controlled comfort, live guide, photo stops included.
- 20 reviews
- 4.90★
- Duration
- 2h
- start times · Every day
- 4
Chicago Lakefront Electric Bike Tour & Skyline ViewsElectric bike tour along Chicago's lakefront with stops at Navy Pier, Grant Park, and Field Museum. Includes helmets, water, snacks. Best skyline photo spot included.
- 18 reviews
- 4.56★
- Duration
- 45m–1h
Chicago O'Hare Airport Transfer: Private Sedan & PickupPrivate sedan transfer between Chicago downtown and O'Hare Airport. Professional driver, luxury vehicle, 24/7 service. Fixed price for up to 3 passengers, no shared rides.
- 17 reviews
- 5.00★
Chicago O'Hare & Midway: Private Airport Transfer Luxury SUVPrivate airport transfer between Chicago downtown and O'Hare or Midway. Professional drivers, 24/7 service, up to 7 passengers, fixed pricing. FBI-vetted, fully insured.
- 16 reviews
- 5.00★
Chicago to Milwaukee: Harley Museum & Brewery TourDay trip from Chicago to Milwaukee with Harley-Davidson Museum, Miller Brewery tour and tasting, Milwaukee Art Museum, and Public Market. Expert guide and transport included.
- 13 reviews
- 4.38★
- Duration
- 8h–10h
- Fri and Sat
- 08:00
Indoor Skydiving Chicago-Naperville: 2 Flights with InstructorTry indoor skydiving at iFLY Naperville near Chicago with two one-on-one flights in a vertical wind tunnel.
- 13 reviews
- 4.08★
- Duration
- 1h 15m
- start times · Wed–Sun
- 21
O'Hare to Chicago: Private Luxury SUV Transfer & MeetPrivate car service from O'Hare Airport to Chicago hotels. Driver meets you at baggage claim with real-time tracking, luggage help, and water. Fixed pricing, 24/7 availability.
- 13 reviews
- 4.69★
Chicago: Architecture, Mob History & Pedway Underground TourSpanish-guided walking tour of Chicago's Loop, Riverwalk, and Pedway. Covers Al Capone history, Rookery Building, Cloud Gate, and Chicago Cultural Center. Full day tour.
- 11 reviews
- 5.00★
- Duration
- 3h
- Mon–Fri
- 10:30
Chicago: Self-Guided Audio Tour & 15 AttractionsSelf-guided audio tour of Chicago's top attractions including Field Museum, Millennium Park and Navy Pier. Explore at your own pace with 6-day access to audio guides and map.
- 9 reviews
- 3.89★
- Duration
- 3h–9h
- start times · Every day
- 6
Kayaking near Chicago: Starved Rock tandem tours with eaglesPaddle tandem kayaks through Starved Rock's sandstone canyons on the Illinois River, spotting bald eagles and lotus flowers with a guide.
- 7 reviews
- 4.43★
- Duration
- 2h
Chicago Walking Tour of Highlights: Free bike or kayak rentalTwo-hour guided walk through Millennium Park, Cloud Gate, Riverwalk and Magnificent Mile with free 2-hour bike or kayak rental valid within 3 days.
- 7 reviews
- 5.00★
- Duration
- 2h
- Every day
- 15:30
Horseback Riding in Mississippi: Calm Horses, Petting ZooHorseback riding in Mississippi with calm horses, petting zoo animals and a wrangler who leads each rider.
- 7 reviews
- 5.00★
- Duration
- 1h
Private Chicago Foodie Tour: Taste 5 Iconic EatsPrivate walking food tour through Chicago with a local guide, tasting Portillo's hot dogs, Al's Italian Beef, deep dish pizza.
- 6 reviews
- 5.00★
- Duration
- 4h
- start times · Every day
- 3