Canada's Leading International Student Tour Operator!



From: $429.00

Number of days: 4

Join our tour of Chicago, a city that wears its American heart proudly on its sleeve. Built on an unrivalled tradition of jazz and blues, amazing architecture, a beautiful harbourfront and a mile of shopping, Chicago offers much to its visitors.  Visit the iconic Chicago Zoo for free, Lincoln Park, Navy Pier, and more! Optional activities include visiting the famous Skydeck, standing at 1353 feet tall, enter a glass cube sticking 4.3 feet outside, or join us on a boat cruise down the Chicago River, learning all about Chicago`s history and unique architecture! On the way back, enjoy very cheap shopping at an outlet mall and duty free!

We are looking forward to seeing you soon!

Please select the MONTH and DATE in the calendar below.

Blow around the Windy City, where the pizza is deep dish, the comedy clubs are hilarious, and the music is soulful.  Shop for top brands on the Magnificent Mile, or walk down and visit the arts and cultural centres along the Cultural Mile.  Feast on deep dish pizza, enjoy a classic Chicago hotdog, or order your "cheeseburger, cheeseburger, cheeseburger" at The Billygoat Tavern.  Your trip includes luxury coach transportation, 3 nights quad hotel accommodation, city tours, all taxes and an ISX tour leader to add to the fun!

  • Motorcoach transportation
  • 3 nights hotel (quad accommodation)
  • 3 breakfasts
  • Tours of Chicago neighborhoods and sights
  • Lots of free time to explore downtown Chicago, The Magnificent Mile, and more.
  • An ISX tour leader
  • Optional activities

PLAN YOUR JOURNEY - We are looking forward to welcoming you on your BEST. TRIP. EVER. but we would hate it if you miss your trip. To help plan your journey and not be late please check the TTC website for closures and delays.

Trip price (starting at): $429 *

*Tax included 

Some countries are eligible to travel to the United States under the visa waiver program. Remember, it is your responsibility to make sure you have the correct documentation for crossing the border as per our terms and conditions. If you are unsure please contact our office. If your country is not listed below, you will need a visa to travel to the US. You must be a citizen or national of the following countries* to be eligible to travel to the United States under the VWP.

Andorra, Australia, Austria, Belgium, Brunei, Chile, Czech Republic, Denmark, Estonia, Finland, France, Germany, Greece, Hungary, Iceland, Ireland, Italy, Japan, Latvia, Liechtenstein, Lithuania, Luxembourg, Malta, Monaco, Netherlands, New Zealand, Norway, Poland, Portugal, San Marino, Singapore, Slovakia, Slovenia, South Korea, Spain, Sweden, Switzerland, Taiwan*United Kingdom** Please check here for the current countries

**To be eligible to travel under the VWP, British citizens must have the unrestricted right of permanent abode in England, Scotland, Wales, Northern Ireland, the Channel Islands, and the Isle of Man. 


  • 7:30am: Depart from Toronto - 100 Queens Park (ROM), ouside of Museum subway station
  • 10:00am: Go through US Immigration (I-94 Card/$6 Border fee)
  • 11:30am: Drive to Chicago
  • Lunch stop, enjoy movies and music
  • 9:0pm: Arrive in Chicago
  • Check into hotel
  • Free time for dinner near the hotel


  • 7:30am: Wake up call
  • 8:30am: Breakfast at the hotel
  • 9:30am: Depart from the Hotel
  • 10:30am: Enjoy Gangsters Tour of Chicago
  • 12:00 pm: See Chicago from the 360 Chicago*
  • 2:30pm: Meet your Tour leader to walk to the architectural boat cruise of Chicago
  • 3:15pm: Enjoy an Architectural Boat Cruise of Chicago*
  • 5:00 pm: Meet the bus Outside the Wrigley Building
  • Enjoy the beautiful view of Chicago
  • Visit the University of Chicago
  • 7:30pm: Drive to Navy Pier
  • 10:30pm: Meet at the Drop-off point to return to the Hotel


  • 7:00am: Wake up call
  • 8:00am: Breakfast at the Hotel
  • 9:00am: Depart from the Hotel
  • 9:30am: Visit the Sky Deck Tower at the Willis Building*
  • 11:00am: Lunch Break on N.Clark
  • 12:00 pm: Free time at Lincoln Park Zoo
  • 2:30 pm: Visit Millennium Park
  • 3:00pm: Visit the Art Institute*
  • 7:30pm : Join your tour leader for a group dinner
  • 9:30pm: Bus Returns to the Hotel
  • Ask your Leader about Chicago Nightlife (+21 ID required)


  • 7:00am: Wake up call and breakfast at the Hotel
  • 8:30am: Leave the Hotel
  • Drive to Toronto
  • 1.5 Hours at Outlet Shopping Mall at Michigan City
  • Duty free shopping
  • Go through the Canadian border
  • 10:00pm: Approximate time of return to Toronto
  • Please note: Itinerary is subject to change due to unforeseen circumstances

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