and Get up to C$15 OFF
◊ Applies to bookings for 3+ travelers. Book by Jun 30, 2018.  Learn more
Best Price Guarantee

Find our lowest price to destinations worldwide, guaranteed

Easy Booking

Search, select and save - the fastest way to book your trip

24/7 Customer Care

Get award-winning service and special deals by calling 1-888-766-3163

Free Mobile App

Our deals are mobile,
just like you

Book Flights from Toronto to Chicago

Find great value on flights from Toronto to Chicago with CheapOair! Plan a vacation to Chicago and savour breath-taking view of its skyline from Sears Tower which is the tallest building in North America and boasts of wonderful architecture. Enjoy the exotic wildlife at Lincoln Park Zoo and also take out time for Shedd Aquarium which is home to rare marine species including dolphins. Taste delicious American and Asian cuisines at restaurants in Greektown or explore Lincoln Square to enjoy rare collection of wines. Whatever type of vacation you are looking for, CheapOair will help you save big on flights to Chicago!

  • When does the first flight of the day depart from YTO? 8:20AM United Airlines Flight #843
  • When does the last flight depart to CHI? 8:55PM Porter Airlines Flight #6114
  • What is the travel distance between Toronto and Chicago?437 miles
  • What is the price range for flights from YTO to CHI? C$299 - C$348
  • How many weekly flights are there are between YTO to CHI?There are 99 weekly flights between YTO and CHI.
  • How many daily flights fly between Toronto to Chicago? There are 13 daily flights between YTO and CHI
  • Which is the busiest day in terms of passengers flying from YTO to CHI?Sunday
  • In last 30 days, what is the %age of CHI visitors who spent less than 3 days in the city?83.33 %
  • Which is the nearest airport to Chicago, Illinois?Midway International Airport
  • Which is the nearest airport to Toronto, Ontario?Billy Bishop Toronto City Airport
  • How much does the cheapest return flight from YTO to CHI cost? C$299

Chicago Travel Tools

  • Enjoy great savings on airfares with our Cheap Flights to Chicago
  • Saving big on Chicago hotels has never been easier! With CheapOair finding the right Montreal hotel that suit your need as well as budget is as easy as closing your eyes!
  • Make your trip comfortable as well as budget friendly with CheapOair discounted Chicago car rentals. Book now and save big!

User Reviews

5I love Chicago!

Chicago is such a great place to visit; awesome restaurants, great shopping! - Anita  May 03, 2018
5Visited Chicago to see family

Awesome trip as visited family in Chicago for holiday. Weather was extremely cold (went down to -21C) and would suggest visiting Chicago during May. - Atif  Jan 03, 2018

Submit a Review