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Chicago Trips & Tours

All Chicago tours, river cruises, expedition cruises, and adventure trips. Find the best guided trips and expert planned vacation and holiday packages from over 600 tour companies. 56 trips found. 96 reviews with an average rating of 4.8 for all Chicago trips. See all Chicago Reviews

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Maples and Monuments tour

Cultural

by
4.3 | Great | 30 Reviews
9 Days
$ 167 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Canada, United States, Chicago, Cleveland, Niagara Falls, Toronto
From
$ 1,499

Highlights

  • Entry to the Rock & Roll Hall of Fame Museum
  • Voyage to the Falls Boat Tour
  • Washington DC Night Illumination Tour
  • Entry to 360 Chicago Tower incl. TILT experience
  • Driving tour of Chicago
  • Walking tour of Toronto
  • Driving tour of Philadelphia
More
America From Broadway to Hollywood Summer 2018 - CostSaver tour

Cultural, Education / Learning

4.5 | Great | 100+ Reviews
24 Days
$ 150 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Canada, United States, Chicago, Cleveland, Grand Canyon, Las Vegas, Los Angeles, New York, Niagara Falls, York
From
$ 3,595

Highlights

  • Badlands National Park
  • Bryce Canyon
  • Chicago
  • Des Moines
  • Gettysburg
  • Grand Canyon
  • Jackson
  • Keystone
  • Los Angeles
  • New York
  • Niagara Falls
  • Sioux Falls
  • Washington, D.C.
  • Yellowstone National Park
  • Zion National Park
More
Route 66 with Albuquerque International Balloon Fiesta Summer 2018 tour

Cultural, Education / Learning

4.5 | Great | 100+ Reviews
15 Days
$ 266 per day
Type: Group Tour
Lodging:
Premium - 4 star

Premium - 4 star Lodging Level3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: United States, Albuquerque, Grand Canyon, Las Vegas, Los Angeles, St. Louis
From
$ 3,995

Highlights

  • Scenic drive along Will Rogers Highway, Desert View Drive
  • Orientation of Chicago
  • View the outdoor installations at Cadillac Ranch, the Petrified Forest National Park
  • Visit the Route 66 Association Hall of Fame and Museum, St. Louis, Meramec Caverns, Branson, Will Rogers Memorial Museum, Clinton, Albuquerque, Grand Canyon National Park, Las Vegas, Los Angeles
More
Presidents & Parks tour

Cultural

by
4.3 | Great | 30 Reviews
21 Days
$ 231 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: United States, Chicago, Grand Canyon, Las Vegas, Monument Valley
From
$ 4,850

Highlights

  • Las Vegas party bus
  • Entry to the Rock & Roll Hall of Fame Museum
  • Tour of the famed Mitchell Corn Palace arena
  • Washington DC Night Illumination Tour
  • Entry to Custer State Park
  • Entry to 360 Chicago Tower incl. TILT experience
  • Entry to Yellowstone National Park
  • Jeep tour of Monument Valley with Navajo guide
  • Entry to Grand Teton National Park
  • Driving tour of the Las Vegas Strip
  • Day trip to Grand Canyon National Park
  • Visit Crazy Horse Memorial
  • Visit Mount Rushmore National Memorial
  • Experience sunset at Dead Horse Point outside Moab
  • Jackson Hole Shootout
  • Chuck Wagon Dinner Show
More
From the Windy City to the Big Easy Summer 2018 - CostSaver tour

Cultural, Education / Learning

4.5 | Great | 100+ Reviews
11 Days
$ 181 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: United States, Chicago, Memphis, Nashville, New Orleans
From
$ 1,995

Highlights

  • Chicago
  • Indianola
  • Frankfort
  • Memphis
  • Memphis
  • Nashville
  • New Orleans
More
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Wild Wild West tour

Cultural

by
4.3 | Great | 30 Reviews
18 Days
$ 233 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: United States, Arches National Park, Chicago, Grand Canyon, Las Vegas, Monument Valley
From
$ 4,199

Highlights

  • Las Vegas party bus
  • Tour of Morning Temple Square tour in Salt Lake City
  • Entry to Custer State Park
  • Entry to 360 Chicago Tower incl. TILT experience
  • Entry to Yellowstone National Park
  • Jeep tour of Monument Valley with Navajo guide
  • Entry to Grand Teton National Park
  • Driving tour of the Las Vegas Strip
  • Day trip to Grand Canyon National Park
  • Visit Crazy Horse Memorial
  • Visit Mount Rushmore National Memorial
  • Experience sunset at Dead Horse Point outside Moab
  • Jackson Hole Shootout
  • Chuck Wagon Dinner Show
More
Route 66 Summer 2018 tour

Cultural, Education / Learning

4.5 | Great | 100+ Reviews
15 Days
$ 260 per day
Type: Group Tour
Lodging:
Premium - 4 star

Premium - 4 star Lodging Level3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: United States, Albuquerque, Chicago, Grand Canyon, Las Vegas, Los Angeles, St. Louis
From
$ 3,895

Highlights

  • Scenic drive along Will Rogers Highway, Desert View Drive
  • Orientation of Chicago
  • View the outdoor installations at Cadillac Ranch, the Petrified Forest National Park
  • Visit the Route 66 Association Hall of Fame and Museum, St. Louis, Meramec Caverns, Branson, Will Rogers Memorial Museum, Clinton, Albuquerque, Grand Canyon National Park, Las Vegas, Los Angeles
More
Capones Trail  tour

Cultural

by
4.3 | Great | 30 Reviews
6 Days
$ 233 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: United States, Chicago, Cleveland, New York, York
From
$ 1,399

Highlights

  • Entry to the Rock & Roll Hall of Fame Museum
  • Washington DC Night Illumination Tour
  • Entry to 360 Chicago Tower incl. TILT experience
More
Best of the USA Tour–New York to New York tour

Cultural, Nature & Wildlife, Trekking & Expeditions

4.8 | Excellent | 100+ Reviews
43 Days
$ 137 per day
Type: Small Group Tour
Lodging:
Camping

Camping Lodging LevelTypically involves most nights sleeping in tents (sometimes permanent tented sites) or in rustic cabins and lodges.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: United States, Austin, Chicago, Death Valley, Grand Canyon, Lake Tahoe, Las Vegas, Memphis, Mesa Verde, Monument Valley, Nashville, New Orleans, New York, Niagara Falls, San Francisco, Santa Fe, Yellowstone National Park, York, Yosemite National Park, Sierra Nevada, Death Valley National Park
From
$ 5,899

Highlights

  • Kick off with free time to explore the big apple
  • Break a sweat in death valley and cool off in the spray of niagara falls
  • Tour miller brewery in milwaukee
  • Dance like a cowboy in jackson
  • Meet the navajo in monument valley
  • Hike in stunning national parks
More
New York to Chicago Road Trip tour

Cultural, Nature & Wildlife

4.8 | Excellent | 100+ Reviews
6 Days
$ 175 per day
Type: Small Group Tour
Lodging:
Camping

Camping Lodging LevelTypically involves most nights sleeping in tents (sometimes permanent tented sites) or in rustic cabins and lodges.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: United States, Chicago, New York, Niagara Falls, York
From
$ 1,049

Highlights

  • See the sights in new york city
  • Feel the spray of niagara falls
  • Revel in the beauty of the finger lakes
  • Sample chicago-style deep-dish pizza
More
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Tours & Operators on Stride Awarded and Featured by:

  • National Geographic, Condé Nast Traveler, Travel + Leisure
  • Outside, The New York Times