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United States · solo travel

Solo Travel in Chicago: Small-Group Tours & Safe Experiences

Lakefront runs, deep-dish lunches, river architecture cruises at golden hour. Solo-friendly small-group tours, walking food tours, day trips and workshops in Chicago — meet other travelers, keep your independence, book everything in one place.

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Small-group tours & solo-friendly activities in Chicago

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1h 30m

Small-Group Sightseeing Boat Tour in Chicago

The ultimate custom sightseeing experience in Chicago!

  • Top-rated · 5.0★
  • Free cancellation
From $89 a person
1h to 1h 30m

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River.

  • Top-rated · 4.8★
  • Bestseller
From $39 a person
Join us in the daytime or evening for City lights and breathtaking views
45 min

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire.

  • 4.7★ · 3360 reviews
  • Bestseller
From $28 a person
This tour cruises the Chicago River and Lake Michigan.
1h 30m

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all.

  • 4.7★ · 2360 reviews
  • Bestseller
From $45 a person
Explore Chicago's legendary architecture and history.
1h 30m

Chicago River 90-Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy...

  • Top-rated · 4.7★
  • Bestseller
From $45 a person
Segways are fun and easy to ride!
2h

Chicago Landmarks & Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago?

  • Top-rated · 5.0★
  • Free cancellation
From $70 a person
3h

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour.

  • Free cancellation
  • Half-day
From $48 a person
Berczy Park
3h

Show me the City! A Small Group Walking Tour of Toronto

Show Me the City is rated one of the top 10 rated walking tours in North America.

  • Top-rated · 4.9★
  • Free cancellation
From $40 a person
Guide greets a small-group of travelers in Plaza de Mayo, Beunos Aires, for a sightseeing city tour.
3h to 5h

Buenos Aires Small-Group City Tour

This service is unique due to its specific characteristics: small groups of people per tour, one language per vehicle, and an excellent profile and preparation of the tour guides.

  • Top-rated · 4.8★
  • Bestseller
From $38 a person
The Chicago River, as seen from our stop on wacky Wacker Drive
2h to 4h

Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city.

  • Top-rated · 4.8★
  • Free cancellation
From $50 a person
Cathedral Valley
8h

Small Group Tour of Pikes Peak and the Garden of the Gods from Denver

Take a guided tour through the most picturesque locations in Colorado Springs.

  • Top-rated · 4.9★
  • Bestseller
From $189 a person
2h

Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago.

  • Top-rated · 4.9★
  • Free cancellation
From $35 a person
1h 30m

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides!

  • Top-rated · 4.8★
  • Bestseller
From $37 a person
2h

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Discover Chicago at your own pace with Big Bus.

  • Bestseller
  • Free cancellation
From $49 a person
3h

Milan Duomo & The Last Supper Skip-the-Line Small Group Tour

This experience gives you guaranteed access to Milan Duomo and The Last Supper, two spots that usually sell out long in advance.

  • 4.6★ · 2990 reviews
  • Bestseller
From $162 a person
A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.
3h

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history.

  • Top-rated · 4.9★
  • Free cancellation
From $80 a person
Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!
3h

Chicago Favorites Ultimate Food and Walking Tour

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour.

  • Top-rated · 4.8★
  • Bestseller
From $85 a person
1h 30m

Small-Group La Scala Museum Tour in Milan

Located right in the heart of the city, just a few steps away from the Duomo and the Galleria Vittorio Emanuele II, stands the true "Temple of Music": La Scala Theatre and its...

  • 4.6★ · 710 reviews
  • Free cancellation
From $55 a person
2h

Chicago Walking Tour: Historic Treasures of Chicago

Learn about the great architectural landmarks of Michigan Avenue and State Street.

  • Top-rated · 4.9★
  • Free cancellation
From $35 a person
1h 30m

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past.

  • Top-rated · 5.0★
  • Free cancellation
From $35 a person
Beverly Hills
4h 30m

Small-Group Tour of Chicago Neighborhoods: North and South Side

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks.

  • 4.5★ · 53 reviews
  • Free cancellation
From $125 a person
Chicago Food Tour
2h

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider stories...

  • Top-rated · 4.8★
  • Free cancellation
From $87 a person
Buenos Aires City Council
3h

Small Group Tour of Buenos Aires Historic

Welcome to the Small-Group Walking Tour of Downtown Buenos Aires!

  • Free cancellation
  • Instant confirmation
From $15 a person
3h

New Orleans Small-Group City Tour by Van

Come hang out with a local for 2.5 to 3 hours and find out why they are so passionate about living in New Orleans.

  • Top-rated · 4.8★
  • Free cancellation
From $69 a person

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