Christmas, Private, Tour Reviews, Walking ToursChicago Private Christmas & Christkindlmarket Walk / August 12, 2026 ★ 5.0Chicago Private Christmas & Christkindlmarket WalkFrom $7281 reviews
Guided, Private, Tour Reviews, Tours, Walking ToursChicago Loop Private Walking Tour with a Guide / August 11, 2026 ★ 1.0Chicago Loop Private Walking Tour with a GuideFrom $1321 reviews
Private, Tour Reviews, WorkshopsPrivate Shooting and Spinning DIY Painting Class in Chicago / August 11, 2026 ★ 5.0Private Shooting and Spinning DIY Painting Class in ChicagoFrom $991 reviews
Private, Tour Reviews, ToursChicago Private Instagram Car Tour (Private & All-Inclusive) / August 11, 2026 ★ 5.0Chicago Private Instagram Car Tour (Private & All-Inclusive)From $7501 reviews
Cruises & Boat Tours, Lake Michigan Cruises, Private, Sailing, Tour ReviewsPrivate Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise / August 11, 2026 Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline CruiseFrom $492 reviews
Private, Private Drivers, Tour ReviewsOne-Way Private Transfer from Downtown Chicago To MDW by Sedan / August 11, 2026 ★ 5.0One-Way Private Transfer from Downtown Chicago To MDW by SedanFrom $1332 reviews
Private, Private Drivers, Tour ReviewsPrivate SUV Transfer Between O’Hare airport & Downtown Milwaukee WI / August 11, 2026 ★ 5.0Private SUV Transfer Between O’Hare airport & Downtown Milwaukee WIFrom $6002 reviews
Private, Tour Reviews6-Hour Private SUV Transportation Service in Chicago / August 11, 2026 ★ 5.06-Hour Private SUV Transportation Service in ChicagoFrom $1,2002 reviews
Private, Private Drivers, Tour ReviewsMeet and Greet Private Sedan Transfer from ORD to Downtown Chicago / August 11, 2026 ★ 5.0Meet and Greet Private Sedan Transfer from ORD to Downtown ChicagoFrom $2402 reviews
Private, Private Drivers, Tour Reviews, VIPPrivate Luxury 6-Pax SUV Limo Transfer from or to Chicagoland Airport and Suburb / August 11, 2026 ★ 3.0Private Luxury 6-Pax SUV Limo Transfer from or to Chicagoland Airport and Suburb2 reviews
Private, Tour Reviews, Tours, Walking ToursPrivate Wicker Park and Bucktown Walking Tour / August 10, 2026 ★ 5.0Private Wicker Park and Bucktown Walking TourFrom $1952 reviews
Photography Sessions, Private, Tour ReviewsPrivate Photography Session with Local Photographer in Chicago / August 10, 2026 ★ 5.0Private Photography Session with Local Photographer in ChicagoFrom $3252 reviews
Museums, Private, Tour Reviews, Tours, Walking Tours, ZoosLincoln Park Nature Museum & Zoo Private Walking Tour / August 10, 2026 ★ 5.0Lincoln Park Nature Museum & Zoo Private Walking TourFrom $2502 reviews
City Tours, Private, Tour Reviews, ToursPrivate City Tour 6-10ppl / August 9, 2026 ★ 5.0Private City Tour 6-10pplFrom $7702 reviews
Private, Tour ReviewsShooting + Spinning Private Art Experience / August 9, 2026 ★ 5.0Shooting + Spinning Private Art ExperienceFrom $972 reviews
Private, Tour Reviews, Tours, Walking ToursBest of Chicago: Private Walking Tour with a Local / August 9, 2026 ★ 5.0Best of Chicago: Private Walking Tour with a LocalFrom $482 reviews
Private, Tour Reviews, Tours, Walking Tours️ Chicago Instagram Walking Tour (Private & All- Inclusive) / August 9, 2026 ★ 5.0️ Chicago Instagram Walking Tour (Private & All- Inclusive)From $2362 reviews
Private, Private Drivers, Tour ReviewsMeet and Greet Private SUV Transfer from MDW to Downtown Chicago / August 9, 2026 ★ 5.0Meet and Greet Private SUV Transfer from MDW to Downtown ChicagoFrom $3002 reviews
Private, Private Drivers, Tour ReviewsPrivate SUV Transfer from Chicago Downtown to Midway airport / August 9, 2026 ★ 5.0Private SUV Transfer from Chicago Downtown to Midway airportFrom $2403 reviews
Guided, Private, Tour Reviews, Tours, Walking ToursChicago Highlights Private Walking Tour With A Guide / August 8, 2026 ★ 3.9Chicago Highlights Private Walking Tour With A GuideFrom $1293 reviews
City Tours, Private, Tour Reviews, ToursPrivate Holiday City Tour / August 8, 2026 ★ 5.0Private Holiday City TourFrom $4993 reviews
Photography Sessions, Private, Tour ReviewsPrivate Vacation Photoshoot with Photographer in Chicago / August 8, 2026 ★ 3.5Private Vacation Photoshoot with Photographer in ChicagoFrom $1543 reviews
Private, Private Drivers, Tour ReviewsPrivate Transfer from Chicago Airport (ORD) / August 8, 2026 ★ 3.5Private Transfer from Chicago Airport (ORD)From $763 reviews
Half-Day, Observation Decks, Private, Tour Reviews, ToursWelcome to Chicago: Private Half-Day Tour with 360 Observation Deck / August 8, 2026 ★ 5.0Welcome to Chicago: Private Half-Day Tour with 360 Observation DeckFrom $2403 reviews
Guided, Private, Tour Reviews, Tours, Walking ToursPrivate Downtown Chicago TV and Movie Sites Guided Walking Tour / August 8, 2026 ★ 4.5Private Downtown Chicago TV and Movie Sites Guided Walking TourFrom $1323 reviews
Airport Transfers, Private, Private Drivers, Tour ReviewsOne-Way Private Airport Transfer by Sedan / August 7, 2026 ★ 4.0One-Way Private Airport Transfer by Sedan4 reviews
Cooking Classes, Pizza Tours, Private, Tour Reviews, WorkshopsTraveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class / August 7, 2026 ★ 5.0Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking ClassFrom $594 reviews
2-Hour Experiences, Private, Tour Reviews, Tours2 Hour Private Chicago Soul House Tour / August 7, 2026 ★ 4.02 Hour Private Chicago Soul House Tour4 reviews
Private, Private Drivers, Tour ReviewsChicago O`Hare Airport (ORD) to Chicago hotel/address – Arrival Private Transfer / August 7, 2026 ★ 5.0Chicago O`Hare Airport (ORD) to Chicago hotel/address – Arrival Private TransferFrom $754 reviews
Private, Private Drivers, Tour ReviewsPrivate SUV Transfer from Chicago Downtown to O`Hare airport / August 7, 2026 ★ 5.0Private SUV Transfer from Chicago Downtown to O`Hare airportFrom $2404 reviews
Private, Private Drivers, Tour ReviewsPrivate SUV Transfer Between O’Hare airport & Downtown Madison WI / August 6, 2026 ★ 5.0Private SUV Transfer Between O’Hare airport & Downtown Madison WIFrom $8004 reviews
Airport Transfers, Private, Private Drivers, Tour ReviewsPrivate Transfer ORD Airport to Chicago / Milwaukee / Oak Brook / August 6, 2026 ★ 3.5Private Transfer ORD Airport to Chicago / Milwaukee / Oak BrookFrom $454 reviews
Drinking Tours, Gangster & Mob Tours, Nightlife, Private, Pub Crawls, Tour ReviewsPrivate Speakeasy Pub Crawl in Chicago with Local Historian / August 6, 2026 ★ 4.5Private Speakeasy Pub Crawl in Chicago with Local HistorianFrom $1015 reviews
Guided, Private, Tour Reviews, ToursPrivate Chicago Guided Tour with Hotel Pickup / August 6, 2026 ★ 5.0Private Chicago Guided Tour with Hotel PickupFrom $8445 reviews
Architecture Tours, Private, Tour Reviews, ToursPrivate Chicago Architecture Tour / August 6, 2026 ★ 5.0Private Chicago Architecture TourFrom $5395 reviews
Private, Private Drivers, Tour ReviewsORD Airport Private Transfer to/from Chicago / August 6, 2026 ★ 4.8ORD Airport Private Transfer to/from ChicagoFrom $856 reviews
Private, Private Drivers, Tour Reviews, VIPChicago 4-Hour Sightseeing Transfer by Luxury Private Sedan / August 6, 2026 ★ 4.5Chicago 4-Hour Sightseeing Transfer by Luxury Private SedanFrom $1905 reviews
Architecture Tours, Private, Tour Reviews, Tours, Walking ToursPrivate Chicago Architecture Walking Tour / August 6, 2026 ★ 5.0Private Chicago Architecture Walking TourFrom $2116 reviews
Food, Private, Tour Reviews, ToursPrivate Chicago Foodie Tour / August 6, 2026 ★ 5.0Private Chicago Foodie TourFrom $2886 reviews
Private, Tour Reviews, ToursPrivate Frida and Friends Tour in Pilsen / August 6, 2026 ★ 4.5Private Frida and Friends Tour in Pilsen6 reviews
Architecture Tours, Private, Tour Reviews, ToursChicago: Private Architecture Tour – 3 or 6 Hours / August 5, 2026 ★ 4.0Private Architecture Tour – 3 or 6 HoursFrom $7806 reviews
Architecture Tours, Private, Tour Reviews, Tours, VIPPrivate Frank Lloyd Wright Architectural Tour by Luxury Vehicle / August 5, 2026 ★ 3.5Private Frank Lloyd Wright Architectural Tour by Luxury VehicleFrom $3007 reviews
