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The Best Two Week (14-Day) Organized Tours from Chicago

Guided Group Tours, Vacation Packages, or Planned Itineraries

the USA

Looking for the perfect two-week packaged tour departing from Chicago? We've carefully analyzed all of the possible 14 and 15 day tour options from Chicago in the USA based on price, service, guest ratings, comfort, cuisine, and activities in order to find the absolute best organized tour options available. Whether you're seeking a relaxing getaway or an action-packed expedition, these two-week guided organized tours, holiday packages, and tour packages offer the perfect amount of time to indulge in the best of both worlds. From captivating excursions to tantalizing meals, get ready to experience the ultimate escape that will leave you with unforgettable memories and a renewed sense of wanderlust. Great for museums & attractions, food, nightlife, and music, the USA is a terrific destination. So, check out our curated list of tours departing from Chicago to get started with your next trip.


The Top 3 Tours:

  • 15 Days, $5350.94

  • 14 Days, $6318.00

  • 15 Days, $4445.00
USA
The Best 2-Week Tours from Chicago through the USA

Including guided tours, organized tours, holiday packages, all-inclusive vacations, and guided itineraries.

All tour prices are listed in US Dollars before taxes, and come from a base price that is reported by TourRadar. Peak season prices can vary significantly, particularly in destinations where seasonal travel fluctuates dramatically. While we do our best to evaluate all tours to maintain accuracy, always confirm the details directly with TourRadar or the tour company before booking. The information provided on this website is sourced directly from TourRadar and may change at any time.

Organized by Travelling Time 15 Days Chicago to Nashville 9 Destinations
  • Great for Culture Lovers

This tour visits Nashville, Bowling Green, Central City, Louisville, Cleveland, Detroit, Memphis, Chicago, Muscle Shoals, and Tupelo.

  • In-depth Cultural
  • Fully Guided

By Travelling Time
Travelling Time offers local cultural tours through the U.S.. Many of the tours fall into the mid-range price category.



$5,351
on TourRadar

Organized by Travel Talk 14 Days Chicago to San Francisco 22 Destinations
Great for:
  • Culture Lovers
  • History Enthusiasts

This tour visits Chicago, Sioux Falls, Keystone, Badlands National Park, Mount Rushmore National Memorial, Rapid City, Bighorn National Forest, Cody, Yellowstone National Park, Grand Teton National Park, Salt Lake City, Bryce Canyon National Park, Grand Canyon National Park, Flagstaff, Seligman, Las Vegas, Mojave Desert, Beverly Hills, Los Angeles, Santa Barbara, Santa Maria, Carmel, San Francisco, and Monterey.

  • In-depth Cultural
  • Historical
  • Fully Guided

By Travel Talk
Travel Talk is a large international travel company offering trips all over the world. Budget travelers will appreciate the relative affordability of the company's offerings.



$4,423
on TourRadar

Organized by On The Go Tours 15 Days Chicago to Los Angeles 21 Destinations
  • Great for Culture Lovers

This tour visits Chicago, St. Louis, Tulsa, Oklahoma City, Amarillo, Albuquerque, Gallup, Canyon de Chelly National Park, Holbrook, Monument Valley, Page, Grand Canyon National Park, Williams, Seligman, Kingman, Las Vegas, Barstow, Mojave Desert, Beverly Hills, Santa Monica, and Los Angeles.

  • In-depth Cultural
  • Family
  • Fully Guided

By On The Go Tours
On The Go Tours is a large multi-national travel company which offers trips to destinations around the world. Many of their tours are priced in the mid-range category.



$4,445
on TourRadar

Organized by On The Go Tours 14 Days Chicago to San Francisco 23 Destinations
  • Great for Culture Lovers

This tour visits Chicago, Sioux Falls, Sioux City, Badlands National Park, Mount Rushmore National Memorial, Deadwood, Cody, Yellowstone National Park, Grand Teton National Park, Salt Lake City, Bryce Canyon National Park, Grand Canyon National Park, Flagstaff, Seligman, Las Vegas, Beverly Hills, Los Angeles, Solvang, Santa Barbara, Carmel, Monterey, and San Francisco.

  • In-depth Cultural
  • Family
  • Fully Guided

By On The Go Tours
On The Go Tours is a large multi-national travel company which offers trips to destinations around the world. Many of their tours are priced in the mid-range category.



$4,140
on TourRadar

Organized by Journaway 14 Days Chicago to Miami 4 Destinations
  • Great Value: the daily price is lower than average for two-week tours from Chicago in the USA.
  • In Depth: you'll spend a longer amount of time in each place.
  • Independence: immerse yourself in the culture with self guided travel.

Great for:
  • History Enthusiasts
  • Cycling Enthusiasts

This tour visits Chicago, New York City, Washington DC, and Miami.

  • Sightseeing
  • Historical
  • Self-Guided
  • Bike and Barge

By Journaway



$1,867
on TourRadar

How much do two-week tours from Chicago cost?

The average daily price of 2-Week Tours from Chicago in the USA is $280 per day. Prices can vary widely due to the included amenities, length of the trip, number of guests on the tour, and many other factors. If you want more information about prices, we have put together a complete analysis of the costs of 2-Week Tours from Chicago in the USA here.


We partner with TourRadar because they offer the world's largest selection of multi-day organized tours, offering seamless travel experiences while supporting local businesses. It's the perfect way to explore new destinations with ease and confidence.




$280
Average Price Per Day
5
Tours Analyzed
0
Average Rating
4
Tour Companies
32
Average Group Size

Which Tour Companies Offer 2-Week Tours from Chicago?

A number of fantastic tour companies offer two-week tours from Chicago in the USA. These are a few of the best, because they offer the highest rated service, provide the best overall quality, and have the most five-star guest reviews to prove it.


Two Weeks From Destinations in the USA

Wondering where two weeks from tours visit in the USA? With a variety of stops and destinations along the way, there's something for everyone.

Chicago

Chicago is a booming metropolis that sits on the edge of Lake Michigan. It is a thriving and diverse city that has theater, shopping, and high-reaching skyscrapers. It's also home to the Willis Tower (previously the Sears Tower), which at one time was the world's tallest building. Visitors appreciate the many museums, sporting events, and entertainment options around town.

Los Angeles

Los Angeles is a world-famous city with sprawling neighborhoods and a diverse population. In addition to being the home of Hollywood, the city also has many cultural neighborhoods and unique restaurants. Visitors can enjoy behind-the-scenes tours of production companies or wander down Hollywood Boulevard and check out the Walk of Fame. There are also many iconic beach areas including Venice Beach and Malibu.

Las Vegas

Las Vegas is an iconic destination with over-the-top resort hotels, elaborate casinos, grand shows, and a theatrical atmosphere. The city is a popular destination for bachelor and bachelorette parties. It's also a popular conference destination and considered to be a world class entertainment destination.

Grand Canyon National Park

The Grand Canyon is an iconic landmark in the United States. It's located in the state of Arizona and it is surrounded by a national park. The canyon is formed by the Colorado River and the views from the rim are truly breathtaking, particularly at sunrise and sunset. There is an easy stroll along the rim of the canyon, or a much more strenuous hike into the canyon. Along the rim there are many vistas and viewpoints.

More

Other popular destinations for two weeks from tours through the USA include Seligman, Beverly Hills, Sioux Falls, Badlands National Park, and Oklahoma City.


Tour Prices in the USA2-Week Tours from Chicago in North America

Which is cheaper?

Can you save money by traveling independently instead of joining guided two-week tours from Chicago? It's not a simple yes or no. Tours usually include key expenses such as lodging, transportation, meals, entry fees, guides, and activities, which you'd need to manage and pay for individually on your own trip. To figure out the difference, compare the total tour price with the cost of making your own arrangements. Depending on your choices—like opting for budget hotels or premium dining—the cost of a tour might be higher or lower. Be sure to examine the tour inclusions carefully when comparing.

Also, before booking a tour, make sure you know exactly what is included as tour companies sometimes change their itineraries or included amenities to keep them updated with seasonal changes and customer interests.

More Tour Options

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Also, if you're departing from a specific destination, see The Best 3-Day Tours from Las Vegas, The Best 3-Day Tours from San Francisco, The Best 3-Day Tours from New York City, The Best 3-Day Tours from Los Angeles, The Best 3-Day Tours from Asheville, The Best One-Week (7-Day) Tours from Las Vegas, The Best One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from Anchorage, The Best One-Week (7-Day) Tours from Seattle, The Best One-Week (7-Day) Tours from Boston, The Best One-Week (7-Day) Tours from New York City, The Best One-Week (7-Day) Tours from Washington DC, The Best One-Week (7-Day) Tours from Nashville, The Best One-Week (7-Day) Tours from Charleston, The Best One-Week (7-Day) Tours from Denver, The Best One-Week (7-Day) Tours from New Orleans, The Best One-Week (7-Day) Tours from San Francisco, The Best One-Week (7-Day) Tours from Fairbanks, The Best One-Week (7-Day) Tours from Honolulu, The Best One-Week (7-Day) Tours from Rapid City, The Best One-Week (7-Day) Tours from Salt Lake City, The Best One-Week (7-Day) Tours from Jackson, The Best One-Week (7-Day) Tours from Miami, The Best One-Week (7-Day) Tours from Phoenix, The Best One-Week (7-Day) Tours from Chicago, The Best One-Week (7-Day) Tours from Scottsdale, The Best 10-Day Tours from Honolulu, The Best 10-Day Tours from Las Vegas, The Best 10-Day Tours from Boston, The Best 10-Day Tours from Anchorage, The Best 10-Day Tours from Washington DC, The Best 10-Day Tours from Los Angeles, The Best 10-Day Tours from Denver, The Best 10-Day Tours from Nashville, The Best 10-Day Tours from Bozeman, The Best 2-Week Tours from Las Vegas, The Best 2-Week Tours from San Francisco, The Best 2-Week Tours from Los Angeles, The Best 2-Week Tours from New York City, The Best 2-Week Tours from Honolulu, The Best 2-Week Tours from Anchorage, The Best 2-Week Tours from Atlanta, The Best 2-Week Tours from Denver, The Best 2-Week Tours from Miami, The Best 2-Week Tours from Boston, The Best 2-Week Tours from Seattle, The Best 2-Week Tours from Phoenix, or The Best 2-Week Tours from Salt Lake City for more package tour options.

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