The 15 Best City Tours in Chicago

Delicious Donuts & City Sights: Chicago's Original Donut Tour - Walking Through Chicago’s Loop Between Tastings

★★★★★★★★★★5.0 · 1,389 reviews · 2 hours (approx.) · from $70Our pick

Sample Chicago donuts, hear local stories, and see Loop landmarks on a two-hour walking tour with vegan and allergy-friendly options.

“This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.”

Check availability →Read our full review

Chicago Architecture Tours, Chicago River Cruises, City Tours, Cruises & Boat Tours, Tour Reviews, Tours

Chicago City Tour with Architecture River Cruise Option

2.Chicago City Tour with Architecture River Cruise Option

★★★★★★★★★★5.0 · 705 reviews · 2 to 4 hours (approx.) · from $49

See Chicago by climate-controlled minibus, with Loop landmarks, skyline stops, expert guides, and an optional 75-minute architecture cruise.

“It was fabulous. The tour guides were amazing and fun carefree way to learn about the city. Will do it again”

Check availability →Read our full review

Chicago Speedboat Rides, City Tours, Lake Michigan Cruises, Tour Reviews

City Cruises Chicago: Seadog Lakefront Speedboat Ride

3.City Cruises Chicago: Seadog Lakefront Speedboat Ride

★★★★★★★★★★4.4 · 642 reviews · 30 - 75 minutes · from $42

Review of Chicago’s Seadog speedboat ride, with skyline views, history, music, splashes, family tips, and Extreme Thrill details.

“The only bad thing about this was that it didn’t last long enough. Loved it. Got soaked just what I expected and wanted, nearly lost my eyelashes due to the speed of the boat. Would defo recommend this.”

Check availability →Read our full review

Chicago Sightseeing Bus & Driving Tours, City Tours, Tour Reviews, Tours

Chicago City Minibus Tour

4.Chicago City Minibus Tour

★★★★★★★★★★5.0 · 516 reviews · 2 hours (approx.) · from $49

See Chicago’s skyline, landmarks, parks, and neighborhoods on a two-hour minibus tour with live stories and four photo stops.

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

Check availability →Read our full review

Chicago Dinner Cruises, City Tours, Cruises & Boat Tours, 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

★★★★★★★★★★4.0 · 348 reviews · 2 hours (approx.) · from $66

Review the City Cruises Chicago lunch cruise, with Lake Michigan views, buffet dining, DJ entertainment, practical tips, and honest value advice.

“Really great experience, food fantastic, cruise so pretty as you can see the Chicago skyline and Navy Pier. Only negative experience music was geared to only one age group although there were all ages abc ethnicity.”

Check availability →Read our full review

Chicago Dinner Cruises, City Tours, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Lunch Experiences, Tour Reviews

City Cruises Chicago: Premier Lunch or Dinner Cruise

6.City Cruises Chicago: Premier Lunch or Dinner Cruise

★★★★★★★★★★4.3 · 334 reviews · 2 - 3 hours · from $88

Dine on a three-course meal aboard the Odyssey, with Lake Michigan views, Chicago landmarks, a live DJ, and a 360-degree observation deck.

“Everything was Wonderful from the beginning to end. The servers and Heather were all great!”

Check availability →Read our full review

Chicago Architecture Tours, Chicago Speedboat Rides, City Tours, Cruises & Boat Tours, Tour Reviews

City Cruises Chicago: 75-min Speedboat Architecture Cruise

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

★★★★★★★★★★4.5 · 268 reviews · 1h 15m · from $61

See Chicago’s landmark architecture from a Seadog speedboat, passing through the harbor locks before a fast Lake Michigan finish.

“We went in afternoon and weather was perfect. Thanks to Kat and Tom and our tour guide so sorry I forget his name. Very well run and are about safety.”

Check availability →Read our full review

City Tours, Cycling Tours, Tour Reviews, Tours

Chicago’s Ultimate City Bike Tour

8.Chicago’s Ultimate City Bike Tour

★★★★★★★★★★5.0 · 233 reviews · 3 hours (approx.) · from $59

Ride Chicago’s lakefront and Loop with a guide, seeing major landmarks, public art, and skyline views on a relaxed three-hour bike tour.

“This is a great way to get an overview of the city. Including hidden gems your won’t find on your own.”

Check availability →Read our full review

Chicago Dinner Cruises, City Tours, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Lake Michigan Cruises, Lunch Experiences, Tour Reviews

City Cruises Chicago: Lake Michigan Lunch or Dinner Cruise

9.City Cruises Chicago: Lake Michigan Lunch or Dinner Cruise

★★★★★★★★★★4.0 · 217 reviews · 2 hours · from $66

Review of City Cruises Chicago’s Lake Michigan buffet cruise, with skyline views, DJ entertainment, rooftop games, dining, price, and practical tips.

“It was so nice!! Artisha was our server she is amazing and never missed a beat with whatever we needed or asked of her!!”

Check availability →Read our full review

City Tours, Private, Tour Reviews, Tours

Chicago Private Custom City Tour with Hotel Pick Up

10.Chicago Private Custom City Tour with Hotel Pick Up

★★★★★★★★★★5.0 · 201 reviews · 3 to 4 hours (approx.)

Explore Chicago by private vehicle with hotel pickup, guided stops at Millennium Park, Wrigley Field, Hyde Park, and more.

“Scott is very knowledgeable, eloquent, and keep you interested throughout the driving in the streets of Chicago. He will tell you stories that will blow up your mind.”

Check availability →Read our full review

Chicago Architecture Tours, Chicago Sightseeing Bus & Driving Tours, City Tours, Cruises & Boat Tours, Tour Reviews, Tours

Chicago: City Minibus Tour with Optional Architecture Cruise

11.City Minibus Tour with Optional Architecture Cruise

★★★★★★★★★★4.8 · 141 reviews · 2 - 4 hours · from $48

See Chicago’s key sights by climate-controlled minibus, with photo stops and an optional 75-minute architecture cruise on the river.

“Informative as well as humorous - good driver - good way to see downtown highlights as well as the nice area near Lincoln Park. Highly recommend.”

Check availability →Read our full review

Chicago River Cruises, City Tours, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Lunch Experiences, Tour Reviews

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

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

★★★★★★★★★★4.7 · 128 reviews · 2 hours - 150 minutes · from $84

Review of City Cruises Chicago’s dining cruise, with riverfront architecture, chef-prepared meals, brunch mimosas, practical tips, and value advice.

“Great experience, receiving a voucher due to us not being able to go out. But just the experience, food, staff and captain were amazing! Our server Jamie gave us the best experience. We will be visiting again in the summer!”

Check availability →Read our full review

Chicago Ghost Tours, City Tours, Tour Reviews, Tours

Embers of the Windy City: Chilling Chicago Ghost Tours

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

★★★★★★★★★★4.5 · 121 reviews · 1 hour (approx.) · from $32Best value

Explore Lincoln Park’s haunted parks, pubs, and crime sites on a one-hour Chicago ghost walk with lively storytelling and small groups.

“It was a nice walk around Lincoln park. Just wished you could go into places! Tour guide was very nice.”

Check availability →Read our full review

City Tours, Food, Food & Drink, Tour Reviews, Tours

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

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

★★★★★★★★★★5.0 · 111 reviews · 2 hours (approx.) · from $78

Sample Chicago hot dogs, deep-dish pizza, and Italian beef while walking the Loop with a local guide in a small group.

“Fantastic tour! Loved learning about the local “flavors” of Chicago! Tour guide was very knowledgeable and friendly.”

Check availability →Read our full review

Chicago Architecture Tours, City Tours, Private, Tour Reviews, Tours

Best of Chicago: Architecture & Highlights City Private Tour

15.Best of Chicago: Architecture & Highlights City Private Tour

★★★★★★★★★★5.0 · 94 reviews

Walk Chicago’s architectural core from the Chicago Theatre to Cloud Gate, with local stories, Pedway access, train fare, and tastings.

“Great walking tour, learnt many facts & tasted some local treats. Rich was a great guide, we were even treated to his rendition of a couple of songs & some music to walk the Pedway!!! Highly recommend”

Check availability →Read our full review