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Fares from $104 One Way, $179 Round Trip from Toronto to Chicago

Prices starting at $179 for return flights and $104 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Toronto

Flights from Toronto to Chicago - Frequently Asked Questions

Are there non-stop flights from Toronto to Chicago?

You're in luck — there are 3 airlines which offer direct services from Toronto, ON Airport (YYZ-Pearson Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.). Here are some of the best:

  • Air Canada
  • United Airlines
  • American Airlines
What is the shortest flight from Toronto to Chicago?

It can be as a short and sweet as 1 hour and 48 minutes. If you strongly believe your vacation hours should be spent 'vacationing' rather than flying, you'll enjoy the flight from Toronto to Chicago.

What airlines fly from Toronto to Chicago most frequently?

The airlines that offer the most frequent flights between Toronto, ON Airport (YYZ-Pearson Intl.) and Chicago, IL Airport (ORD-O'Hare Intl.) include Air Canada (AC). This well-known option operates 182 flights on the route each month. United Airlines (UA) will also get you to your destination in comfort. Offering 88 flights per month between Toronto and Chicago, it's another popular airline to look into.

Route Information for Flights from Toronto to Chicago

Origin Airport IATA CodeYTO
Destination Airport IATA CodeCHI
Distance436 mi
Direct Flight AirlinesAmerican Airlines, Air Canada, JAL, Alaska Airlines, Aer Lingus, Qantas, ANA, Air New Zealand, United Airlines, British Airways
Earliest Flight Arrival12:50PM UTC
Latest Flight Arrival10:42PM UTC

Flights Review

Dec 30, 2019

What could have turned into a nightmare with delays, transitioned smoothly thanks to United. Unlike my horrible experience with AA earlier that week.

Nov 28, 2019

Staff during the flight very friendly. But after arriving in Toronto all staff of AirCanada seemed to be in a hurry and couldn't spend one second in helping me find my gate. When I asked help many of them were very rude, but not all of them.

Nov 26, 2019

Love Porter Airlines!

Oct 6, 2019

Air Canada has always been great to my family.

Sep 30, 2019

Yes, I strongly dislike having to pay for my bag. I’d prefer one free checked bag and charge for second bag. You want customers to fly your airline and travelers need luggage so figure out a better way.

Jul 30, 2019

Thanks for great service!

Jun 16, 2019

Just late leaving Toronto so just barely made it to my connection.

Dec 1, 2018

Will continue to fly with United Airlines for future trips

Oct 2, 2018

Porter is great

Sep 19, 2018

My husband’s missing luggage was delivered one day after we returned home. As it was not delivered within the four hour window, he tried to call to find out the status of delivery, but only heard recording message. He practically waited the whole time at home and listened for door bell ringing. Despite the delay in getting his luggage, we had positive experience flying Porter for the first time.

Travel from Toronto to Chicago

Travelers from Toronto often enjoy visiting Chicago for weekend trips or longer vacations to experience the exciting attractions, enlightening cultural events, and incredible shopping opportunities the Windy City has to offer. When planning a trip from Toronto to Chicago, search for great deals on flights, hotels, and tickets to local attractions.

Leaving Toronto

When heading to Chicago, you'll fly out of Toronto Pearson International Airport, which is located about 17 miles from downtown. Taxis, buses, and the LINK train are all popular ways to get to the airport from central Toronto. Alternately, you can hop on the Express airport shuttle, which makes regular stops throughout the downtown area. If you plan to drive yourself to the airport, you can choose from the value parking garage or the value parking lot, both located just minutes from the terminals on the LINK line.

Visiting Chicago

Chicago has two airports: Chicago O'Hare International Airport and Chicago Midway International Airport. Both airports are served by public buses, and O'Hare has a stop for the CTA Blue line. You can also head into town via taxi or rent a car at the car rental facilities located at both airports. Once in Chicago, check out the Chicago Historical Society museum to get a better idea of the history and culture of the city, then head out to explore. Visit Navy Pier and Lincoln Park Zoo, or relax at Hyde Park before heading out to the theater district to catch a performance. Summer is a popular time to visit Chicago due to the pleasant weather; temperatures average in the low 80s during the day and in the 60s at night. Winters can be cold, with highs near freezing temperature and lows in the 20s, but prices drop significantly during this time.

Your Trip to Chicago

Whether you spend your Chicago vacation investigating the many museums of the city, shopping on the Magnificent Mile, or soaking up culture at local art galleries, you are sure to have a blast in the Windy City. Whatever your vacation budget, check for great deals on air tickets from Toronto to Chicago, vacation packages, and all of your travel needs.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.