$139 Cheap flight deals from Toronto (YTO) to Chicago (CHI)

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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.

Sun, Oct 5 - Tue, Oct 21
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$398 Roundtrip, found 23 hours ago
$398
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Sun, Oct 5 from Billy Bishop Toronto City to Midway Intl., returning Tue, Oct 21, priced at $398 found 23 hours ago
Sun, Oct 5 - Tue, Oct 21
YYZ
Pearson Intl.
MDW
Midway Intl.
$409 Roundtrip, found 23 hours ago
$409
Roundtrip
found 23 hours ago
Select WestJet flight, departing Sun, Oct 5 from Pearson Intl. to Midway Intl., returning Tue, Oct 21, priced at $409 found 23 hours ago
Sat, Oct 4 - Tue, Oct 14
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$564 Roundtrip, found 2 hours ago
$564
Roundtrip
found 2 hours ago
Select WestJet flight, departing Sat, Oct 4 from Pearson Intl. to O'Hare Intl., returning Tue, Oct 14, priced at $564 found 2 hours ago
Sun, Oct 5 - Tue, Oct 21
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$812 Roundtrip, found 23 hours ago
$812
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Sun, Oct 5 from Billy Bishop Toronto City to O'Hare Intl., returning Tue, Oct 21, priced at $812 found 23 hours ago

Airfares from $139 One Way, $234 Round Trip from Toronto to Chicago

Prices starting at $234 for return flights and $139 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.

Tue, Nov 18 - Sat, Nov 22
YTZ
Toronto
MDW
Chicago
$234 Roundtrip, found 1 hour ago
$234
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Tue, Nov 18 from Toronto to Chicago, returning Sat, Nov 22, priced at $234 found 1 hour ago
Sat, Dec 27 - Fri, Jan 2
YYZ
Toronto
ORD
Chicago
$241 Roundtrip, just found
$241
Roundtrip
just found
Select United flight, departing Sat, Dec 27 from Toronto to Chicago, returning Fri, Jan 2, priced at $241 just found
Sat, Oct 25 - Wed, Oct 29
YYZ
Toronto
MDW
Chicago
$275 Roundtrip, found 3 hours ago
$275
Roundtrip
found 3 hours ago
Select WestJet flight, departing Sat, Oct 25 from Toronto to Chicago, returning Wed, Oct 29, priced at $275 found 3 hours ago
Sat, Oct 25 - Tue, Oct 28
YKF
Kitchener
ORD
Chicago
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Oct 25 from Kitchener to Chicago, returning Tue, Oct 28, priced at $280 found 2 days ago
Sat, Oct 25 - Tue, Oct 28
YHM
Hamilton
ORD
Chicago
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Oct 25 from Hamilton to Chicago, returning Tue, Oct 28, priced at $280 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
3.5-star property

The Whitehall Hotel, BW Premier Collection

8.2/10 Very Good! (3,575 reviews)

Nov 21 - Nov 24

3 night stay

Hamilton (YHM) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was $515, price is now $406 per person
$406
per person
found 1 day ago
Generous breakfast, beautiful room. Convenient to go everywhere.

Reviewed on Sep 3, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,427 reviews)

Nov 21 - Nov 24

3 night stay

Hamilton (YHM) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was $701, price is now $474 per person
$474
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0-star property

Hilton Garden Inn Chicago Downtown/Magnificent Mile

8.4/10 Very Good! (3,910 reviews)

Nov 21 - Nov 24

3 night stay

Hamilton (YHM) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was $650, price is now $493 per person
$493
per person
found 1 day ago
It was close to everything that we came to look for

Reviewed on Sep 28, 2025

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More About Flying To Chicago from Toronto

Route Information for Flights from Toronto to Chicago

Origin Airport IATA Code
YTO
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

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 Orbitz.com 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 Orbitz.com for great deals on air tickets from Toronto to Chicago, vacation packages, and all of your travel needs.

Frequently asked questions

Are there non-stop flights from Toronto to Chicago?
Yep, your unforgettable vacation is just one easy flight away. Wonderful news, isn't it? Take to the skies aboard one of the 3 carriers that fly nonstop from Toronto, ON (YYZ-Pearson Intl.) to ORD. Top options include:

  • Air Canada
  • United Airlines
  • American Airlines

What is the shortest flight from Toronto to Chicago?
It can take just 1 hour and 50 minutes to fly from YYZ to ORD. Settle in and enjoy those window views, because you'll be disembarking in the blink of an eye.
What airlines fly from Toronto to Chicago most frequently?
Air Canada (AC) is one of the carriers with the most flights from YYZ to ORD. It offers 152 flights on this route every month. Taking a vacation is one of life's greatest pleasures, and this carrier will get you where you need to go. Also consider the great fares from United Airlines (UA). Offering 91 flights each month between Toronto and Chicago, they make the journey just as enjoyable as the destination.
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 2021 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 from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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More Destinations

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.