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This Weekend's Flight Deals from Toronto to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $167 One Way, $287 Round Trip from Toronto to Chicago

Prices starting at $287 for return flights and $167 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.

Need A Hotel In Chicago After Your Flight?

Hotels In Top Chicago Neighborhoods

Near North Side
176 hotels

Kinzie Hotel

4.0 out of 5.0


The Loop
87 hotels


River North
82 hotels

ACME Hotel Company

3.5 out of 5.0


Stay Near Exciting Chicago Attractions

More About Flying To Chicago from Toronto

Route Information for Flights from Toronto to Chicago

Origin Airport IATA CodeYTO
Destination Airport IATA CodeCHI
Distance436 mi
Direct Flight AirlinesAmerican Airlines, Qatar Airways, Alaska Airlines, Air Canada, Qantas, SAS, Royal Jordanian, Finnair, Copa Airlines, Air New Zealand, United Airlines
Earliest Flight Arrival1:25PM UTC
Latest Flight Arrival11:20PM 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.

Flights from Toronto to Chicago - Frequently Asked Questions

Are there non-stop flights from Toronto to Chicago?

Work out your ideal travel dates, because there is. You can fly from Billy Bishop Airport to Midway Intl. Airport (MDW) in one simple journey with Porter Airlines.

What is the shortest flight from Toronto to Chicago?

It can take just 2 hours and 37 minutes to jet from Pearson Intl. Airport (YYZ) to O'Hare Airport. Kick back and enjoy those window views, because you'll be landing in a heartbeat.

What airlines fly from Toronto to Chicago most frequently?

Porter Airlines offers the most services from Toronto to Chicago, with 99 monthly flights.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.