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15 Best City Tours In Chicago

The best of Chicago.

The 15 best city tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.

15 Best City Tours In Chicago

Delicious Donuts & City Sights: Chicago's Original Donut Tour - Stop-by-stop: Doughnut Vault, Firecakes, Stan’s, and Do-Rite
Chicago, City Tours, Food & Culinary Tours, Tour Reviews, Tours

Delicious Donuts & City Sights: Chicago’s Original Donut Tour

Chicago City Tour with Architecture River Cruise Option - The Loop, shopping streets, and The Bean area: a quick hit without the walking pain
Chicago, Chicago River Architecture Cruises, City Tours, Cruises & Boat Tours, Sightseeing & City Tours, Tour Reviews, Tours

Chicago City Tour with Architecture River Cruise Option

2.Chicago City Tour with Architecture River Cruise Option

Small-group Chicago architecture tour by minibus, with optional open-top river cruise. Hit the Loop, skyline views, and top icons fast.

5.0

“My family and I had the best time! Rick did such a fantastic job in showing us around Chicago and learning about the history of such a marvellous city! A 10/10 tour will definitely be coming back to do again”

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Chicago City Minibus Tour - Palmer House Pickup: A Clean Start Right Where You’ll Want To Be
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Chicago City Minibus Tour

4.Chicago City Minibus Tour

See Chicago highlights in 2 hours on an air-conditioned minibus with live narration, key photo stops, and easy downtown pickup.

5.0

“great way to see the city, it felt like a private tour! our guide was very knowledgeable, friendly, & fun!”

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City Cruises Chicago: Signature Lunch Cruise on Lake Michigan - Where You Start: Navy Pier Without the Wrong-Boat Stress
Chicago, City Tours, Cruises & Boat Tours, Dinner & Cocktail Cruises, Lake Michigan Cruises, Lunch Experiences, Tour Reviews

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

5.City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

A 2-hour small-group lunch cruise on Lake Michigan from Navy Pier with buffet lunch, DJ entertainment, and skyline views.

4.0

“It was not clear exactly where the ship was. I only saw 600 E Grand Avenue, we were at the pier at 11:45 for a 12:30 sailing. It took us 44 minutes to find the boat. We got there at 12:29 and just made it. I would have been extremely angry if I lost over…”

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City Cruises Chicago: 75-min Speedboat Architecture Cruise - Civic Opera House to Trump Tower: Bridges, Parks, and Wacker Street Views
Chicago, Chicago River Architecture Cruises, City Tours, Cruises & Boat Tours, Speedboat & Jet Boat Rides, Tour Reviews

City Cruises Chicago: 75-min Speedboat Architecture Cruise

Chicago's Ultimate City Bike Tour - Meeting at Bobby’s and getting your bike sorted
Bike Tours, Chicago, City Tours, Cycling Tours, Tour Reviews, Tours

Chicago’s Ultimate City Bike Tour

7.Chicago’s Ultimate City Bike Tour

A 3-hour Chicago bike tour for $59, riding mostly bike paths along Lake Michigan and major museums, with time for photos and stories.

5.0

“You get to see all the touristy sights. Our tour guide Dan was so knowledgeable with a great sense of humour. Beautiful scenery. Would highly recommend”

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City Cruises Chicago: Lake Michigan Lunch or Dinner Cruise - Boarding at Navy Pier: the part that trips people up
Chicago, City Tours, Cruises & Boat Tours, Dining Experiences, Dinner & Cocktail Cruises, Dinner Experiences, Lake Michigan Cruises, Lunch Experiences, Tour Reviews

City Cruises Chicago: Lake Michigan Lunch or Dinner Cruise

Chicago Private Custom City Tour with Hotel Pick Up - The Loop and Downtown: 45 minutes that helps everything else make sense
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Chicago Private Custom City Tour with Hotel Pick Up

9.Chicago Private Custom City Tour with Hotel Pick Up

Chicago private custom city tour with hotel pickup. See Millennium Park, Loop, Lincoln Park, Hyde Park and Wrigley Field in 3–4 hours.

5.0

“This private tour is totally worth it! We had a driver and a guide take us around various parts of the city in a very spacious Landrover. Matt our guide was very knowledgeable and Harold our driver was great at maneuvering around the traffic which there was a lot of during the Memorial Day weekend.…”

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Chicago: City Minibus Tour with Optional Architecture Cruise - Grant Park and Buckingham Fountain: the classic Chicago postcard
Chicago, Chicago River Architecture Cruises, City Tours, Cruises & Boat Tours, Hop-On Hop-Off & Bus Tours, Sightseeing & City Tours, Tour Reviews, Tours

Chicago: City Minibus Tour with Optional Architecture Cruise

Embers of the Windy City: Chilling Chicago Ghost Tours - Lincoln Park after dark: what the vibe is really like
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Embers of the Windy City: Chilling Chicago Ghost Tours

Chicago Food Tour: Taste the City’s Most Iconic Eats - Meeting at the Chicago Theatre and Staying On Time
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Chicago Food Tour: Taste the City’s Most Iconic Eats

Best of Chicago: Architecture & Highlights City Private Tour - The Chicago Pedway: indoor shortcuts that make winter feel optional
Chicago, City Tours, Private, Private & Custom City Tours, Sightseeing & City Tours, Tour Reviews, Tours

Best of Chicago: Architecture & Highlights City Private Tour

City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise - Brunch vs lunch vs dinner: what actually changes
Chicago, City Tours, Cruises & Boat Tours, Dining Experiences, Dinner & Cocktail Cruises, Dinner Experiences, Lunch Experiences, Tour Reviews

City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise

City Cruises Chicago: Fireworks Signature Dinner Cruise - Buffet Dinner: What’s Included and How to Eat Like You Mean It
Chicago, City Tours, Cruises & Boat Tours, Dining Experiences, Dinner & Cocktail Cruises, Dinner Experiences, Tour Reviews

City Cruises Chicago: Fireworks Signature Dinner Cruise

15.City Cruises Chicago: Fireworks Signature Dinner Cruise

A Chicago Lake Michigan fireworks dinner cruise with a buffet, DJ, and Navy Pier views. Smart casual, weather-dependent fireworks, great value.

4.0

“The wrong boat is listed on the confirmation email, it had the Spirit of Chicago when it was the Spirit of Navy Pier. They do not honor dress code, sport casual no gym shoes or flip flops-that’s not true because there were a plether of each. The bathrooms do not lock, I was urinating and…”

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More City Tours In Chicago

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Explore Chicago

From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.