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Most Popular Airlines Flying to Chicago

See which airlines fly to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.
Porter Airlines logo Porter Airlines
Air Canada logo Air Canada
United Airlines logo United Airlines
WestJet logo WestJet
American Airlines logo American Airlines
Delta Air Lines logo Delta Air Lines
Etihad Airways logo Etihad Airways
Frontier Airlines logo Frontier Airlines
Alaska Airlines logo Alaska Airlines
avianca logo avianca
EgyptAir logo EgyptAir
Air Transat logo Air Transat
Aeromexico logo Aeromexico
Sun Country Airlines logo Sun Country Airlines
Japan Airlines logo Japan Airlines
Royal Jordanian logo Royal Jordanian
Scandinavian Airlines logo Scandinavian Airlines

Latest Flight Deals to Chicago

These are the best offers on flights to Chicago you’ll find over the next 60 days, with savings of up to CAD 722. Don’t miss out!

37%
Toronto Chicago
Air Canada Air Canada
One way
Economy
Tue, Nov 10
CAD 261
CAD 417
49%
Vancouver Chicago
WestJet WestJet
One way
Economy
Thu, Oct 15
CAD 301
CAD 585
-6%
Montreal Chicago
Air Canada Air Canada
One way
Economy
Tue, Oct 27
CAD 485
CAD 458
65%
Calgary Chicago
Air Canada Air Canada
One way
Economy
Sun, Oct 11
CAD 203
CAD 578
-23%
Edmonton Chicago
WestJet WestJet
One way
Economy
Sun, Oct 11
CAD 838
CAD 681
76%
Saskatoon Chicago
WestJet WestJet
One way
Economy
Thu, Oct 15
CAD 192
CAD 816
62%
Winnipeg Chicago
WestJet WestJet
One way
Economy
Fri, Oct 16
CAD 240
CAD 636
56%
Ottawa Chicago
WestJet WestJet
One way
Economy
Thu, Oct 15
CAD 274
CAD 628
78%
Victoria Chicago
WestJet WestJet
One way
Economy
Thu, Oct 15
CAD 207
CAD 929

When is the cheapest time to book flights to Chicago?

Departure:

What is the cheapest month to book a one-way flight from Toronto to Chicago?

Average price of one-way tickets from Toronto to Chicago booked on Trip.com over the past 12 months.

For a one-way flight from Toronto to Chicago, fares are lowest in January (CAD 262) and highest in October (CAD 344).

CAD 344
CAD 303
CAD 262
CAD 221
    Cheapest
  • CAD 344
    Oct
  • CAD 318
    Nov
  • CAD 303
    Dec
  • CAD 262
    Jan
  • CAD 270
    Feb
  • CAD 303
    Mar
  • CAD 302
    Apr
  • CAD 286
    May
  • CAD 293
    Jun
  • CAD 296
    Jul
  • CAD 295
    Aug
  • CAD 279
    Sep

What is the cheapest month to book a return flight from Toronto to Chicago?

Average price of return tickets from Toronto to Chicago booked on Trip.com over the past 12 months.

For a return flight from Toronto to Chicago, fares are lowest in September (CAD 361) and highest in October (CAD 487).

CAD 487
CAD 424
CAD 361
CAD 298
    Cheapest
  • CAD 487
    Oct
  • CAD 426
    Nov
  • CAD 424
    Dec
  • CAD 384
    Jan
  • CAD 367
    Feb
  • CAD 389
    Mar
  • CAD 382
    Apr
  • CAD 399
    May
  • CAD 395
    Jun
  • CAD 408
    Jul
  • CAD 392
    Aug
  • CAD 361
    Sep

Which day of the week is cheapest to fly from Toronto to Chicago?

Data is based on the past 12 months and shows the average weekly airfare from Toronto to Chicago on different days of the week according to Trip.com.

Based on Trip.com data from the past 12 months, the cheapest day to fly from Toronto to Chicago is Tuesday. The average fare on this day is usually lower than on other days. Try to avoid flying on Sunday as fares are usually the highest.

CAD 323
CAD 303
CAD 283
CAD 263
  • CAD 290
    Mon
  • CAD 283
    Tue
  • CAD 288
    Wed
  • CAD 294
    Thu
  • CAD 287
    Fri
  • CAD 289
    Sat
  • CAD 323
    Sun

Round-trip fights to Chicago

Whether it's a quick getaway or a business trip to remember, our 3–7 day round trips are perfect for experiencing Chicago affordably.

8 day trip
Thu, Oct 15- Thu, Oct 22
8 day trip
Calgary
Chicago
CAD 299
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5 day trip
Thu, Oct 15- Mon, Oct 19
5 day trip
Kelowna
Chicago
CAD 324
Search
3 day trip
Fri, Oct 16- Sun, Oct 18
3 day trip
Vancouver
Chicago
CAD 341
Search
4 day trip
Thu, Oct 15- Sun, Oct 18
4 day trip
Edmonton
Chicago
CAD 356
Search
4 day trip
Wed, Oct 21- Sat, Oct 24
4 day trip
Montreal
Chicago
CAD 374
Search
8 day trip
Wed, Oct 21- Wed, Oct 28
8 day trip
Toronto
Chicago
CAD 496
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Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight priceCAD 162
Cheapest return ticket priceCAD 266
Cheapest monthDecember
Peak season for travelJanuary
Flight distance701.97km
Average flight time2 hours 6 minutes
Popular airlinePorter Airlines

Frequently asked questions: Booking Chicago flights

  • How long is the flights to Chicago?

    • Approx. 1 hour 54 minutes to fly from Toronto to Chicago.
    • Approx. 3 hours 39 minutes to fly from Calgary to Chicago.
    • Approx. 4 hours 20 minutes to fly from Vancouver to Chicago.
    • Approx. 5 hours 21 minutes to fly from Edmonton to Chicago.
  • You can book cheaper flights in the following ways:
    • Search for tickets to a city or airport near Chicago.
    • Look up different airlines that have flights to Chicago.
    • Browse different departure dates from the same month.
    • Filter for different departure times from the same day.
    • Check for discount information on various social media sites.
    • Explore deals and discounts on airline websites.
  • Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is October. The average price of flight tickets to Chicago in October is CAD 437.
  • Flight tickets to Chicago are the cheapest in December compared to other months, the average price is CAD 616.
  • Popular airlines with flights to Chicago: American Airlines, United Airlines, and Frontier Airlines.

Find Cheap Flights with Trip.com

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Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed on this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within the last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.