Experience Chicago

Giving you all the history, mystery and fun that the Windy City has to offer!

Home of the 1908 World's Fair and the 1st Skyscraper

Travel planning isn’t always an easy task for groups. There’s a lot to consider such transportation, hotels, site entries, meals, and more, and it all has to fall in line for the trip to work for everyone’s enjoyment. If you’re not up for that task, we would like to take that on that task for your group and save you time and frustration trying to do the planning on your own. A Traveler’s Rest representative will assist you through the whole process from planning to returning safely home with your group.

School class trips – Band trips – Scouting groups – Theater groups – Church groups – Bank groups – Reunion groups – Military groups – Park district groups – Scholar groups – Senior groups

Why choose Experience Chicago?

It’s a legitimate question when there are several other travel companies offering similar services service to St. Louis.

  • You’ll be supporting a small but experienced family company that is independently  owned.
  • Competitive pricing because we’re a smaller company and don’t have all of the corporate expenses to feed. 
  • Knowledgeable and professional guides with years of experience. 
  • We offer educational and historical programs for students and groups for an interactive experience the other companies don’t offer.

Perhaps our biggest advantage over other student travel companies is that we have been escorting tour groups to Midwest cities like St. Louis for years. We work with the St. Louis Convention & Visitor’s Bureau, historical sites and attractions, and we know all the nuances and policies of securing proper site reservations and getting in and out of the sites. Group travel is our wheelhouse.

Ready to start planning your St. Louis Experience trip?

A Traveler’s Rest rep will assist you through the entire process

Step 1: Contact us with specific details about your group.
Step 2: Select the sites you want to visit.
Step 3: Select your meal/hotel options.
Step 4: Review your itinerary with your rep.
Step 5: Price out your trip/Sign contract
Step 6: Sell your trip to your group members.
Step 7: Pay for all trip members
Step 8: Final review of travel plans
Step 9: Show up on time for departure                          
Step 10: Enjoy your Chicago Experience!

Willis Tower Window Walk

Cost of Tours

There’s a number of factors that influence the cost of experience tours; gas prices, entry fees, program costs, food prices, etc. We want your business, so we work to give you the experience tour that you would expect, but also to keep our prices low and competitive.

Included in the price:

Not included:

Site Reservations

What You Need To Know:

Included In The Price:

  • There is only a specific number of allowable group tour slots at the sites per day. 
  • We work diligently to get you the site reservations you want for your group. 
  • Group reservations are guaranteed on a first come first serve basis.
  • Best advice is to make your site request with us as soon as possible. 
  • Many groups get their itineraries set 4-6 months prior to the date of travel.

Adler Planetarium

Partial List of sites to Choose

frank-lloyd-wright-home-near-chicago (1)
Frank Lloyd Wright Home

Sites & Attractions:

  • Chicago Water Tower 
  • Willis Tower Skydeck
  • Hancock Tower Observatory
  • Millennium Park & the Bean
  • Grant Park & Buckingham Fountain
  • The Magnificent Mile
  • Brookfield Zoo
  • Lincoln Park Zoo
  • Navy Pier
  • Frank Lloyd Wright Homes
  • Chicago Botanical Gardens
  • Wrigley Field
  • United Center
Shedd Aquarium
Shedd Aquarium


  • Museum of Science & Industry
  • The Field Museum
  • Adler Planetarium
  • The Shedd Aquarium
  • Chicago Art Institute
  • Children’s Museum
  • Various Ethnic Museums
  • Illinois Holocaust Museum

*This is a partial list of museums, sites and attractions. Inquire about additional sites.

Navy Pier
Navy Pier


  • Navy Pier
  • Lake Michigan Cruise
  • Theater Shows
  • Sports Games
  • Food Tours
  • Ghost Tours
  • Gangster Tours 
  • Chicago River Architectural Cruise
  • Six Flags Over Mid-America

Educational programs available at all listed museum sites

Numerous Yummy Food Options

Partial List of Programs to Choose (30-60 minute programs)

Some programs are free others have a cost and there’s a range of various programs to choose from. Tell us what interests you and we’ll tell you what’s available. 

  • St. Louis Zoo
  • St. Louis Science Center
  • Cahokia Mounds
  • Union Station Aquarium Complex
Experience Chicago 1


Good food is an important part of travel, we make every effort to ensure everyone gets fed and enjoys their meals. 

We make every effort to make sure that food allergies and special diets are respected, however, per your contract we cannot be responsible for an individual’s diet or food allergy. Restaurants we use do try to accommodate for food allergies and dietary restrictions, but it is not always possible. We highly suggest that if someone has a severe food allergy and has diet restrictions that they bring their own food for best assurance of their health and safety. 

It is suggested that we get your site reservations secured first. It easier to decide the best meals options based on the sites reservations and time slots you get. Several St. Louis sites have group meal options and on-site restaurants.

Lunch and Dinner Options:

  • Hot breakfast is typically included with hotel.
  • Several dine-in lunch/dinner options and boxed lunch/dinner options
  • Some sites offer meal vouchers with group entry.

These sites have on-site group meal capabilities:

  • National Jefferson Expansion Memorial Arch & Museum
  • Union Station Aquarium
  • St. Louis City Museum
  • St. Louis Science Center and Imax 
  • St. Louis Zoo 
  • Grant’s Farm
  • Six Flags Amusement Park

Other Options:

  • Lunch/Dinner cruise on board a paddle-wheeler on the Mississippi River
  • Golden Corral Buffet
  • Emo’s Pizza
  • Old Spaghetti Factory

Sample Itineraries

There are a number of factors that can influence travel plans so each of our itineraries are customized to fit the needs of your group. Some sites can be quick visits, but a number of sites are multi-hour visits.

We are unable to guarantee that you will get site reservations in the order you select due to reservations already in the system taking up time slots. We will do our best for you, but best advice here is to be flexible and get your requests to us as soon as possible. Single or multiple day itineraries possible.

Chicago has a wide range of activities for a wide range of interests that displaying sample itineraries wouldn’t do justice to the numerous possibilities. It really depends on the make-up up your group and the time you have to visit. Contact your TRT rep to brainstorm the possibilities for your group and to receive sample itineraries.

1 Day

  • Arrive in Chicago
  • Museum of Science & Industry
  • Lunch
  • Drive the Magnificent Mile
  • Photo opp at the Bean
  • Willis Tower Skydeck 
  • Navy Pier
  • Lake Michigan Dinner Cruise
  • Home

1 Day (Alternate)

  • Arrive in Chicago
  • Shedd Aquarium
  • Stingray Activity
  • Lunch
  • Field Museum of Natural History
  • Willis Tower Skydeck
  • Photo opp at the Bean
  • Home

2 Days

Day 1

  • Arrive in Chicago
  • Drive the Magnificent Mile
  • Photo opp at the Bean
  • Willis Tower Skydeck
  • Lunch
  • Shedd Aquarium
  • Beluga Whale Educational Program
  • Photo opp Buckingham Palace
  • Dinner
  • Theater Show

Day 2

  • Hotel breakfast
  • Museum of Science & Industry
  • Lunch
  • Chicago River Architectural Cruise
  • Navy Pier
  • Dinner
  • Home
Need a 3 day Itinerary

3 Days

Day 1

  • Union Station Aquarium
  • Behind the Scenes Aquarium Program, on-site lunch
  • Bush Stadium Tour
    St. Louis City Museum, on-site dinner

Day 2

  • National Jefferson Expansion Museum and Arch, on-site lunch
  • Cahokia Mounds
  • St. Louis Zoo
  • Dinner on the Hill
  • Ted Drewes Frozen Custard

Day 3

  • Merrimac Caverns
    On to Hannibal, Mo.
  • Lunch
  • Mark Twain Home &
  • Museum
  • Mark Twain Cave
  • Dinner
  • Home

Group Tour Request

We’ve escorted individuals, families, politicians, generals, admirals, rock stars, all kinds of groups, and nearly 60,000 school kids since 2005!