Cycling Tours, Hiking & Trekking, Tour Reviews, ToursFright Hike: Chicago Halloween Bike Tour / August 5, 2026 ★ 5.0Fright Hike: Chicago Halloween Bike TourFrom $547 reviews
Gangster & Mob Tours, Private, Tour Reviews, ToursPrivate Al Capone Gangster Tour in Chicago / August 5, 2026 ★ 4.5Private Al Capone Gangster Tour in ChicagoFrom $5397 reviews
Tour Reviews, Tours, Walking ToursChicago: Magnificent Mile Walking Tour / August 5, 2026 ★ 4.5Magnificent Mile Walking TourFrom $357 reviews
Ghost Tours, Tour Reviews, ToursChicago: Ghost Bus Tour of Haunted Locations / August 5, 2026 ★ 4.2Ghost Bus Tour of Haunted LocationsFrom $546 reviews
Cycling Tours, Food, Food & Drink, Tour Reviews, ToursChicago: Downtown Family Food Tour by Bike with Sightseeing / August 5, 2026 ★ 4.9Downtown Family Food Tour by Bike with SightseeingFrom $797 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
3-Hour Experiences, Gangster & Mob Tours, Private, Tour Reviews, Tours, VIPChicago: 3-Hour Private Speakeasy Cocktail VIP Tour / August 5, 2026 ★ 5.03-Hour Private Speakeasy Cocktail VIP TourFrom $9507 reviews
Tour Reviews, Tours, Walking ToursWalking Tour: Pilsen Chicago – Creativity & Community / August 5, 2026 ★ 5.0Walking Tour: Pilsen Chicago – Creativity & Community7 reviews
Cycling Tours, Tour Reviews, ToursChicago Amazing Lakefront Bike Tour / August 5, 2026 ★ 3.5Chicago Amazing Lakefront Bike TourFrom $448 reviews
2-Hour Experiences, Evening Experiences, Segway Tours, Tour Reviews, Tours2 Hour Chicago Pier Fireworks & Evening Segway Tour / August 5, 2026 ★ 5.02 Hour Chicago Pier Fireworks & Evening Segway TourFrom $777 reviews
1-Day Tours, Breweries, City Tours, Drinking Tours, Tour Reviews, ToursChicago to Milwaukee Day Trip with Brewery Tour & City Highlights / August 5, 2026 ★ 5.0Chicago to Milwaukee Day Trip with Brewery Tour & City HighlightsFrom $1258 reviews
Architecture River Cruises, Architecture Tours, City Tours, Cruises & Boat Tours, Tour Reviews, Tours, VIPChicago Luxury Minibus City Tour and Architecture River Cruise / August 5, 2026 ★ 4.5Chicago Luxury Minibus City Tour and Architecture River CruiseFrom $498 reviews
Architecture Tours, Historical Tours, Tour Reviews, Tours, Walking ToursSmall Group History And Architecture Walking Tour of Chicago / August 4, 2026 ★ 4.5Small Group History And Architecture Walking Tour of ChicagoFrom $648 reviews
Historical Tours, Tour Reviews, ToursHistorical Fireboat River Tour / August 4, 2026 ★ 5.0Historical Fireboat River TourFrom $479 reviews
Tour Reviews, Tours, Walking ToursThe Deep Pockets Of Graceland Cemetery Walking Tour / August 4, 2026 ★ 5.0The Deep Pockets Of Graceland Cemetery Walking TourFrom $459 reviews
Drinking Tours, Historical Tours, Tour Reviews, Tours, Walking ToursWalking Tour: Historic Chicago Pubs in River North and the Loop / August 4, 2026 ★ 5.0Walking Tour: Historic Chicago Pubs in River North and the LoopFrom $659 reviews
Canoes & Kayaks, Tour Reviews, ToursChicago: Moonlight Paddle Tour on the Chicago River / August 4, 2026 ★ 4.2Moonlight Paddle Tour on the Chicago RiverFrom $589 reviews
Cruises & Boat Tours, Tour Reviews, Tours, Walking Tours, Willis Tower Skydeck TicketsChicago Highlights Walking Tour with Skydeck & Cruise / August 4, 2026 ★ 4.2Chicago Highlights Walking Tour with Skydeck & CruiseFrom $1898 reviews
Guided, Pizza Tours, Tour Reviews, Tours, Walking ToursChicago: Downtown Pizza Guided Walking Tour with Tastings / August 4, 2026 ★ 5.0Downtown Pizza Guided Walking Tour with TastingsFrom $739 reviews
3-Hour Experiences, Gangster & Mob Tours, Private, Tour Reviews, ToursChicago: Private 3-Hour Al Capone Gangster Tour / August 4, 2026 ★ 4.8Private 3-Hour Al Capone Gangster TourFrom $8809 reviews
Architecture Tours, Tour Reviews, Tours, Walking ToursChicago Walking Tour: See Inside Art Deco Masterpieces / August 4, 2026 ★ 4.9Chicago Walking Tour: See Inside Art Deco MasterpiecesFrom $358 reviews
Audio Tours, Guided, Self-Guided Tours, Tour Reviews, ToursChicago Self-Guided Audio Tour / August 4, 2026 ★ 4.0Chicago Self-Guided Audio TourFrom $69 reviews
Cycling Tours, Tour Reviews, ToursChicago Amazing Lakefront Bike Tour / August 4, 2026 Chicago Amazing Lakefront Bike TourFrom $3912 reviews
2-Hour Experiences, Millennium Park Tours, Tour Reviews, Tours, Walking ToursChicago: Downtown Loop & Millennium Park 2 Hour Walking Tour / August 4, 2026 ★ 5.0Downtown Loop & Millennium Park 2 Hour Walking TourFrom $495 reviews
Ghost Tours, Scavenger Hunts, Self-Guided Tours, Tour Reviews, ToursHaunted Chicago Exploration Game and Tour / August 4, 2026 ★ 4.0Haunted Chicago Exploration Game and TourFrom $76 reviews
Guided, Millennium Park Tours, Self-Guided Tours, Tour Reviews, Tours, Walking ToursChicago Millennium Park Self-Guided Walking Tour / August 4, 2026 ★ 4.5Chicago Millennium Park Self-Guided Walking TourFrom $145 reviews
Scavenger Hunts, Self-Guided Tours, Tour Reviews, ToursEastside Chicago The Heist Exploration Game and Tour / August 4, 2026 ★ 4.0Eastside Chicago The Heist Exploration Game and TourFrom $710 reviews
Food, Food & Drink, Tour Reviews, Tours, Walking ToursChicago: River North Walking Food Tour / August 4, 2026 ★ 4.7River North Walking Food TourFrom $9911 reviews
Architecture Tours, Guided, Historical Tours, Tour Reviews, ToursArchitecture & History Guided Tour along the Chicago Riverwalk / August 4, 2026 ★ 5.0Architecture & History Guided Tour along the Chicago Riverwalk12 reviews
Architecture Tours, Tour Reviews, Tours, Walking ToursChicago: Evolution of the Skyscraper Walking Tour / August 4, 2026 ★ 4.9Evolution of the Skyscraper Walking TourFrom $3510 reviews
Ghost Tours, Historical Tours, Tour Reviews, ToursPrairie Avenue Haunted History Tour and Ghost Hunt / August 4, 2026 ★ 5.0Prairie Avenue Haunted History Tour and Ghost HuntFrom $4011 reviews
Breweries, Drinking Tours, Tour Reviews, Tours, Walking ToursOktoberfest Walking Brewery Tour in Logan Square / August 4, 2026 ★ 5.0Oktoberfest Walking Brewery Tour in Logan SquareFrom $2510 reviews
Ghost Tours, Tour Reviews, ToursGhosts of Chicago Family Friendly Ghost Tour / August 4, 2026 ★ 4.0Ghosts of Chicago Family Friendly Ghost TourFrom $2912 reviews
Ghost Tours, Historical Tours, Tour Reviews, Tours, Walking ToursChicago Ghosts & Haunted History Walking Tour / August 4, 2026 ★ 5.0Chicago Ghosts & Haunted History Walking TourFrom $4911 reviews
Tour Reviews, ToursChicago: Downtown Highlights Running Tour / August 4, 2026 ★ 5.0Downtown Highlights Running TourFrom $4910 reviews
Lake Michigan Cruises, Tour Reviews, ToursSmall Group Lake Michigan Tour / August 4, 2026 ★ 5.0Small Group Lake Michigan TourFrom $6013 reviews
Architecture Tours, Historical Tours, Tour Reviews, Tours, Walking ToursChicago History and Architecture Walking Tour / August 4, 2026 ★ 4.6Chicago History and Architecture Walking TourFrom $4913 reviews
Historical Tours, Museums, Private, Tour Reviews, ToursPrivate Chicago History Museum Tour / August 4, 2026 ★ 5.0Private Chicago History Museum TourFrom $16212 reviews
Architecture Tours, Cruises & Boat Tours, Historical Tours, Tour Reviews, Tours, Walking ToursChicago History and Architecture Walking Tour with Boat Cruise / August 4, 2026 ★ 4.5Chicago History and Architecture Walking Tour with Boat CruiseFrom $10410 reviews
Helicopter Tours, Tour Reviews, ToursChicago Helicopter 25-Mile Tour for up to Three Passengers / August 4, 2026 ★ 4.5Chicago Helicopter 25-Mile Tour for up to Three Passengers11 reviews
City Tours, Ghost Tours, Historical Tours, Tour Reviews, ToursThe Devil in the White City: A Haunting History Tour / August 4, 2026 ★ 4.5The Devil in the White City: A Haunting History TourFrom $6417 reviews
Cycling Tours, Food, Food & Drink, Guided, Tour Reviews, ToursChicago: Westside Food Tasting Bike Tour with Guide / August 4, 2026 ★ 4.8Westside Food Tasting Bike Tour with GuideFrom $9916 reviews
