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Chicago Trips & Tours

62 trips from 600 tour companies with 96 reviews

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. Average rating of 4.8 for all Chicago trips.

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Maples and Monuments tour

Cultural

by
4.3 | Great | 30 Reviews
9 Days
$ 157 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
$ 1,409

Highlights

  • Walking tour of Toronto
  • 360 Tower with TILT experience, Chicago
  • Night illumination tour, Washington, DC
  • Voyage to the Falls boat tour, Niagara Falls
  • 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, 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
$ 151 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, Yellowstone National Park, York, Yosemite National Park, Santa Fe, Sierra Nevada, Death Valley National Park
From
$ 6,499

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

Trekking & Expeditions, Cultural, Nature & Wildlife

4.8 | Excellent | 100+ Reviews
6 Days
$ 144 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
$ 862

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
Best of the USA Tour–San Fran to San Fran tour

Nature & Wildlife

4.8 | Excellent | 100+ Reviews
43 Days
$ 151 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, Yellowstone National Park, York, Yosemite National Park, Santa Fe, Sierra Nevada, Death Valley National Park, Philadelphia
From
$ 6,499

Highlights

  • Look for wildlife in yellowstone and yosemite
  • Learn about navajo culture in the southwest
  • Rock out in memphis
  • Follow the trail of independence from philadelphia to washington dc
  • Get a taste of cowboy culture
More
Chicago to San Francisco Road Trip tour

Cultural, Nature & Wildlife, Trekking & Expeditions

4.8 | Excellent | 100+ Reviews
16 Days
$ 112 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, Lake Tahoe, San Francisco, Yellowstone National Park, Yosemite National Park
From
$ 1,799

Highlights

  • Camp along the mississippi river
  • Hike the badlands
  • Marvel at yellowstone's geysers
  • Chill out at lake tahoe
  • Meet the wildlife of grand teton national park
  • Explore the streets of san francisco
More
Coast to Coast Camping Westbound tour

Cultural, Nature & Wildlife, Trekking & Expeditions

4.8 | Excellent | 100+ Reviews
22 Days
$ 114 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, Lake Tahoe, New York, Niagara Falls, San Francisco, Yellowstone National Park, York, Yosemite National Park
From
$ 2,512

Highlights

  • Explore the big apple
  • Feel the spray of niagara falls
  • Brush shoulders with cowboys in america's west
  • Camp under the star-filled skies of the plains
  • Hike in beautiful yellowstone and yosemite national parks
More
Epic Adventure (Until Mar 2019) tour

Local Immersion & Homestays

by
3.9 | Great | 20 Reviews
55 Days
$ 161 per day
Type: Group Tour
Lodging:
Basic - 2 star

Basic - 2 star Lodging LevelYou'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.

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, Albuquerque, Boston, Charleston, Chicago, Cleveland, Dallas, Grand Canyon, Las Vegas, Los Angeles, Memphis, Miami, Montreal, Monument Valley, New Orleans, New York, Niagara Falls, Panama City, Philadelphia, Quebec, Texas, Toronto, York, Zion National Park
From
$ 8,849

Highlights

  • Experience some of the world's largest hotels & casinos
  • Go wild in Vegas with a Party Bus
  • Visit Fort Worth Stockyards
  • Visit the Sixth Floor Museum
  • Visit the World Trade Center
  • See the famous neighbourhoods of New York such as Soho, Greenwich Village and TriBeCa
  • See Wall Street and the NYSE
  • See Museum Row including the Metropolitan Museum of Art and Guggenheim Museum
  • Visit fashionable Fifth Avenue & see St. Patrick's Cathedral, Rockefeller Center & Tiffany's
  • See Harlem's Apolo Theatre
  • Scenic drive through Maine's wilderness
  • Cross the Canadian Border/Arrive in Quebec
  • Explore the only walled city in North America
  • Stroll the streets on a walking tour
  • Drive through the American Midwest's beautiful farmlands
  • Enjoy an evening in Madison, home to the University of Wisconsin
  • Explore Custer State Park
  • Visit Mt Rushmore
  • Discover a Native American legend at the Crazy Horse Memorial
  • Visit a panoramic viewpoint for photos
  • Capture some incredible photos with a visit to a panoramic viewpoint
More
North by North East tour

Local Immersion & Homestays

by
3.9 | Great | 20 Reviews
13 Days
$ 158 per day
Type: Group Tour
Lodging:
Basic - 2 star

Basic - 2 star Lodging LevelYou'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.

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, Boston, Chicago, Cleveland, Montreal, Niagara Falls, Quebec, Toronto
From
$ 2,059

Highlights

  • Scenic drive through Maine's wilderness
  • Cross the Canadian Border/Arrive in Quebec
  • Explore the only walled city in North America
  • Stroll the streets on a walking tour
More
The Sumptuous Soul of America (Luxury Gold - Summer 2018) tour

Cultural

4.8 | Excellent | 6 Reviews
14 Days
$ 416 per day
Type: Group Tour
Lodging:
Luxury - 5 star

Luxury - 5 star Lodging LevelThe highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.

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
$ 5,825

Highlights

  • New Orleans: Join a Local Expert to tour one of the city's mysterious above ground cemeteries
  • New Orleans: See the Southern mansions of the Garden District.
  • Chicago: Experience a Highlight Dinner at a classic Chicago chophouse, Gibson's Bar and Steakhouse.
  • Dining Summary: 13 Breakfasts (BB), 1 Lunch (L) and 8 Dinners (DW).
  • Natchez: Learn to make the signature drink of the South, the Mint Julep, before an elegant, four-course Southern dinner in the period surroundings of the Monmouth Historic Inn and Gardens.
  • New Orleans: Join your Travelling Concierge for a Farewell Celebration Dinner accompanied by a lively jazz trio at Arnaud’s.
  • Chicago: Appreciate the variety of impressive styles and achievements in design during your architectural river cruise, as a Local Expert reveals how the city was transformed after the Great Fire of 1871.
  • Memphis: Visit the National Civil Rights Museum.
  • Chicago: Experience a world class Chicago hotel at The Gwen.
  • Louisville: A favourite of Kentucky Derby attendees, The Brown Hotel is an opulent choice amongst travellers who will find a blend of Georgian Elegance, timeless Southern charm and impeccable service.
  • Memphis: The Westin Memphis Beale Street Hotel connects you to the unmistakable sound, culture and history of the blues, whilst offering you a soothing and relaxing retreat.
  • Nashville: Experience the finest in Southern hospitality at Sheraton Grand Nashville Downtown.
  • Natchez: The Monmouth Historic Inn and Gardens offers a unique combination of hospitality, world-class service and luxurious surroundings, set in a historic background.
  • New Orleans: The iconic family-owned Hotel Monteleone offers an unparalleled combination of Southern hospitality, world-class service and historic surroundings inside the French Quarter.
  • St Louis: Four Seasons Hotel St Louis is a five-star hotel with epic views of the Gateway Arch, located in the heart of downtown.
  • Louisville: Visit Churchill Downs on a private tour and meet the world famous horse jockey, Charles Woods Jr.
  • Nashville: Visit the Country Music Hall of Fame and get a private behind the scenes look at the songwriting process with a local songwriter and singer.
More
Splendour in the American Heartland (Summer 2018) tour

Cultural

4.8 | Excellent | 6 Reviews
8 Days
$ 422 per day
Type: Group Tour
Lodging:
Luxury - 5 star

Luxury - 5 star Lodging LevelThe highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.

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, Nashville
From
$ 3,375

Highlights

  • Chicago: Enjoy a sumptuous Highlight Dinner at a classic Chicago chophouse, Gibson's Bar and Steakhouse.
  • Nashville: Enjoy a Farewell Celebration Dinner.
  • Dining Summary: 7 Breakfasts (BB), 1 Lunch (L) and 4 Dinners (DW).
  • Chicago: Experience the greatest highs and best views of the city from the observatory atop 360 Chicago.
  • Bowling Green: The Corvette is America on wheels. The National Corvette Museum pays homage to this most famous sports car.
  • Chicago: Its love affair with state-of-the-art high-rise means its history is written across the sky and there is no better vantage point than from the deck of an architectural river cruise.
  • St Louis: Get a bird's-eye view of the city atop the famed St Louis Gateway Arch.
  • Chicago: Experience a world class Chicago hotel at The Gwen, a Luxury Collection Hotel, and soak in the energy and glamour of Chicago in the 1930s.
  • Louisville: A favorite of Kentucky Derby attendees, The Brown Hotel is an opulent choice amongst travellers, visitors, and locals to the Louisville downtown.
  • Nashville: Experience the finest in Southern hospitality at Sheraton Grand Nashville Downtown.
  • St Louis: Four Seasons Hotel St Louis is a five-star hotel with epic views of the Gateway Arch in the heart of downtown's entertainment district and Lumière Place Casino.
  • Louisville: Discover the secrets involved in the making of the South's signature spirit at a bourbon distillery with your Master of Malt expert before enjoying a sample.
  • Nashville: Attend a live taping of America's longest running live radio program at the Grand Ole Opry.
  • St Louis: Join an exclusive guided tour of the Fabulous Fox Theatre.
More
Music and Heritage tour

Cultural

by
4.4 | Great | 100+ Reviews
20 Days
$ 146 per day
Type: Private Guided
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, Lake Michigan, Memphis, Nashville, New Orleans, St. Louis
From
$ 2,914

Highlights

  • Explore millennium Park where you'll find the Jay Pritzer Pavilion, Crown Fountain, Cloud Gate, Lurie Garden and McCormick Tribune Plaza
  • Enjoy sightseeing at the Navy Pier, an amusement park on the shore of Lake Michigan
  • Visit St. Charles, a charming little town on the Missouri River
  • See magnificent Mile and the 360 Chicago attraction of the John Hancock Tower
  • Visit the National Civil Rights Museum, the Bass Pro Pyramid or the Fire Museum
  • Visit to the Mississippi State Capitol, built in 1901, and the Mississippi Governor's House
More
Grand Northern tour

Local Immersion & Homestays

by
3.9 | Great | 20 Reviews
26 Days
$ 153 per day
Type: Group Tour
Lodging:
Basic - 2 star

Basic - 2 star Lodging LevelYou'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.

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, Boston, Chicago, Cleveland, Grand Canyon, Las Vegas, Montreal, New York, Niagara Falls, Quebec, Toronto, York, Zion National Park
From
$ 3,985

Highlights

  • Scenic drive through Maine's wilderness
  • Cross the Canadian Border/Arrive in Quebec
  • Explore the only walled city in North America
  • Stroll the streets on a walking tour
  • Drive through the American Midwest's beautiful farmlands
  • Enjoy an evening in Madison, home to the University of Wisconsin
  • Explore Custer State Park
  • Visit Mt Rushmore
  • Discover a Native American legend at the Crazy Horse Memorial
  • Visit a panoramic viewpoint for photos
  • Capture some incredible photos with a visit to a panoramic viewpoint
More
Music and Heritage tour

Cultural

by
4.4 | Great | 100+ Reviews
19 Days
$ 172 per day
Type: Private Guided
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
From
$ 2,472
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