$100 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.

Sat, May 3 - Sun, Jun 1
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sat, May 3 from Billy Bishop Toronto City to Midway Intl., returning Sun, Jun 1, priced at $205 found 1 day ago
Sat, May 3 - Tue, May 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$283 Roundtrip, found 3 days ago
$283
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, May 3 from Pearson Intl. to O'Hare Intl., returning Tue, May 13, priced at $283 found 3 days ago
Sun, May 4 - Thu, May 8
YYZ
Pearson Intl.
MDW
Midway Intl.
$398 Roundtrip, found 6 days ago
$398
Roundtrip
found 6 days ago
Select WestJet flight, departing Sun, May 4 from Pearson Intl. to Midway Intl., returning Thu, May 8, priced at $398 found 6 days ago
Sun, May 4 - Thu, May 8
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$571 Roundtrip, found 6 days ago
$571
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Sun, May 4 from Billy Bishop Toronto City to O'Hare Intl., returning Thu, May 8, priced at $571 found 6 days ago

Airfares from $100 One Way, $156 Round Trip from Toronto to Chicago

Prices starting at $156 for return flights and $100 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.

Thu, May 22 - Mon, May 26
YTZ
Toronto
MDW
Chicago
$156 Roundtrip, found 2 days ago
$156
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Thu, May 22 from Toronto to Chicago, returning Mon, May 26, priced at $156 found 2 days ago
Thu, Jun 12 - Mon, Jun 16
YYZ
Toronto
ORD
Chicago
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Air Canada flight, departing Thu, Jun 12 from Toronto to Chicago, returning Mon, Jun 16, priced at $162 found 3 days ago
Mon, Jun 9 - Thu, Jun 19
YYZ
Toronto
ORD
Chicago
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Jun 9 from Toronto to Chicago, returning Thu, Jun 19, priced at $162 found 3 days ago
Thu, Jun 12 - Mon, Jun 16
YYZ
Toronto
ORD
Chicago
$162 Roundtrip, found 6 hours ago
$162
Roundtrip
found 6 hours ago
Select United flight, departing Thu, Jun 12 from Toronto to Chicago, returning Mon, Jun 16, priced at $162 found 6 hours ago
Fri, Jun 6 - Mon, Jun 9
YTZ
Toronto
ORD
Chicago
$199 Roundtrip, found 14 hours ago
$199
Roundtrip
found 14 hours ago
Select Air Canada flight, departing Fri, Jun 6 from Toronto to Chicago, returning Mon, Jun 9, priced at $199 found 14 hours ago

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.

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.