Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Earn rewards on top of your airline miles with Orbitz Rewards

Search for flights on more than 400 airlines

Sign up to receive text alerts about your trip

Selected fares from Toronto to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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.


Save more with Chicago Flight + Hotel packages

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.

*Savings based on all holiday package bookings with Flight + Hotel on from January through December 2017, 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. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

Dec 31, 2018

The staff at the Canadian airport were not as friendly or helpful on my return flight.

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.

Sep 15, 2018

I thoroughly enjoyed my United flight. I may just change my mind on air travel.

Sep 11, 2018

Overhead bins were pretty small. Couldn't fit my "standard" carry on into it

Sep 11, 2018

they give you snacks and free booze

Sep 3, 2018

Could use better directions at airport. Signage is poor to direct passengers to correct line. We were directed by staff to a lone we stood in for half hour. Got to counter only to find out we had been put in the non-USA international flights. Then had to stand in correct line for another halff hour. We weren't the only passengers incorrectly directed. Otherwise, check-in and boarding went fine.

Aug 28, 2018

The change of airport at the last minute was not appreciated.

Aug 14, 2018

Flight delayed by over an hour