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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

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

Chicago Loop walking donut tour with multiple bakery stops, landmark sights, and included samples for a sweet meal. Vegan options available.

Most Popular★ 5.0

“A great experience. Was near to try different donuts from different shops. A good variety and all very tasty. Nick our tour guide was awesome. Friendly, patient, knowledgeable and funny. I highly recommend if you love donuts. Bring hand wipes and some insulin.”

1,389 reviews2 hours (approx.)From $70.00by Underground Donut Tour

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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

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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”

705 reviews2 to 4 hours (approx.)From $49.95by See it ALL Chicago Tours

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City Cruises Chicago: Seadog Lakefront Speedboat Ride - Navy Pier start point and why timing matters
Chicago, City Tours, Speedboat & Jet Boat Rides, Tour Reviews

City Cruises Chicago: Seadog Lakefront Speedboat Ride

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Chicago City Minibus Tour - Palmer House Pickup: A Clean Start Right Where You’ll Want To Be
Chicago, City Tours, Hop-On Hop-Off & Bus Tours, Sightseeing & City Tours, Tour Reviews, Tours

Chicago City Minibus Tour

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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

“Very informative and interesting. You get time to get out and explore. Alan also gave recommendations for Chicago deep dish pizza!”

516 reviews2 hours (approx.)From $49.95by See it ALL Chicago Tours

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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

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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

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6.City Cruises Chicago: 75-min Speedboat Architecture Cruise

A 75-minute Seadog speedboat architecture cruise from Navy Pier. See Chicago River landmarks and Lake Michigan sights with live narration.

★ 4.6

“Sit back, relax, have your camera fully charged! My sister & I sat at the back, I recommend sitting unshaded, unless it's too sunny of a day of course. Drinks, chips & restroom all are on board.”

247 reviewsFrom $44by City Cruises

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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

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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

“Very informative, relaxed and fun bike ride with York. He was great. Easy pace and very flat . Great even for novice cyclists .”

233 reviews3 hours (approx.)From $59.00by Bobby's Bike, Hike & Food Tours - Chicago

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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

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

Chicago Private Custom City Tour with Hotel Pick Up

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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

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

Embers of the Windy City: Chilling Chicago Ghost Tours

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11.Embers of the Windy City: Chilling Chicago Ghost Tours

A $32 small-group Chicago ghost tour through Lincoln Park, with stop-by-stop true crime and haunting stories for a spooky one-hour walk.

★ 4.5

“The tour guide Josephine was the best! She weaved together a little history with each location and we got to know why the area might be haunted.”

121 reviews1 hour (approx.)From $32.00by Windy City Ghosts By US Ghost Adventures

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Chicago Food Tour: Taste the City’s Most Iconic Eats - Meeting at the Chicago Theatre and Staying On Time
Chicago, City Tours, Food, Food & Culinary Tours, Food & Drink, Tour Reviews, Tours

Chicago Food Tour: Taste the City’s Most Iconic Eats

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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

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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

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

City Cruises Chicago River brunch, lunch, or dinner pairs a 3-course meal with glassed-in skyline views and optional narration, DJ, and mimosas.

★ 4.6

“We had a lovely time on our evening cruise, the food and service was excellent, Rudi was so attentive. The weather was perfect to go out on deck and enjoy the scenery and take some wonderful photos. We are two ladies from Sydney Australia and this was a perfect night out, thank you Odyssey Cruises…”

87 reviewsFrom $116by City Cruises

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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

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