MyPortfolio Call Us Open Menu
Contact UsClose

Chicago Vacations

You've found the smartest way to book Chicago packages. Click a price below to see our unique "vacation grid". It's very fast and has a calendar format for easy comparison. Our agents have been to Chicago - call us and we'll help you decide which hotel is right for you.

View Classic Grid

No Advance Testing required at this time.

Loading Search Form
loading form
  • Select Start Dateclose
    Select Additional Dates Close

    Click more departure dates that work for you.

    • Occupancy Information Close

      Select Number of Adults and Child Age AT THE TIME OF TRAVEL

    • We will sort the results by the best matches

      Your Preferences Close

      Select up to 3 of your preferences in order of importance.

      Update Preferences
    • Advanced Search Options

    Best Prices for Vacation Packages To Chicago - per person incl. taxes

    Direct Extensions of Agents Who've Been to Chicago


    In the office now

    Map Location of Chicago

    show map
    Click to view map

    Chicago Vacations

    Chicago, also known as the “Windy City,” is an ideal choice for a weekend getaway! Renowned for its towering skyscrapers, scintillating dishes, vibrant nightlight, and world-class museums and cultural attractions, a Chicago vacation promises to be unforgettable. Whether you are dreaming about a solo travel, planning a family getaway, or itching for a romantic escape, we can help you find affordable flights to Chicago. Visit Chicago and enjoy the great outdoors with a sightseeing tour. Make your way to esteemed museums and galleries like the Shedd Aquarium and the Art Institute of Chicago. Then at night, cozy up at a local bar for a delicious cocktail – whatever you wish to do, you’ll find it all in Chicago. 

    Getting Around: Chicago O’Hare International Airport (ORD) and Midway International Airport (MDW) are the two main gateways for Chicago visitors. O’Hare is located 17 miles from the downtown area and serves over 67 million passengers to and from over 200 destinations around the world. Meanwhile, Midway is located 10 miles from downtown Chicago and offers value-oriented leisure and business travel to over 60 destinations. 

    Chicago is a walkable city with an easy-to-navigate downtown grid. From the airport, visitors can opt for either a cab service, the Chicago Transit Authority (CTA), or Go Airport Express. Looking for a fun way to travel around Chicago? Consider taking the Chicago Water Taxi by Wendella Boats and Shoreline Water Taxi. 

    Where to Stay: Chicago has something in store for everyone. From luxurious accommodations such as The Peninsula Chicago to affordable options like Hotel Blake, there is something for everyone! 

    Weather: Winters in Chicago come with snow and averages -1C to 3C. In spring, temperature typically ranges from 10C to 15C, with a rainfall average of 3.5 to 3.8 inches. Thinking about visiting during the summer? Summers in Chicago hovers around 26C to 33C. On the other hand, fall starts around 21C and gradually drop to 7C as it gets closer to the colder months.


    • Willis Tower 
    • Field Museum
    • Shedd Aquarium
    • Art Institute of Chicago 
    • Adler Planetarium 
    • Lincoln Park Zoo 
    • Navy Pier
    • The Magnificent Mile 

    Start your North American getaway today by giving us a call at 1-800-665-4981!

    Chicago Pictures and Video - click to enlarge images or play videos

    Photos and Videos

    Vacation Packages offered from many airports across Canada

    Vacation Packages to many destinations

    Send me a link to this page