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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
Alaska Airlines logo Alaska Airlines
Frontier Airlines logo Frontier Airlines
Scandinavian Airlines logo Scandinavian Airlines
Air Arabia logo Air Arabia
Japan Airlines logo Japan Airlines
Air Transat logo Air Transat
Turkish Airlines logo Turkish Airlines
avianca logo avianca

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 561. Don’t miss out!

37%
Toronto Chicago
Air Canada Air Canada
One way
Economy
Tue, Nov 10
CAD 242
CAD 386
64%
Vancouver Chicago
WestJet WestJet
One way
Economy
Wed, Dec 16
CAD 197
CAD 551
-62%
Calgary Chicago
Air Canada Air Canada
One way
Economy
Wed, Nov 11
CAD 971
CAD 599
54%
Montreal Chicago
United Airlines United Airlines
One way
Economy
Wed, Dec 16
CAD 205
CAD 449
66%
Edmonton Chicago
Air Canada Air Canada
One way
Economy
Tue, Nov 10
CAD 222
CAD 656
49%
Saskatoon Chicago
Air Canada Air Canada
One way
Economy
Sat, Oct 31
CAD 224
CAD 441
60%
Winnipeg Chicago
Flair Airlines Flair Airlines
One way
Economy
Sun, Nov 1
CAD 285
CAD 716
57%
Ottawa Chicago
Porter Airlines Porter Airlines
One way
Economy
Sat, Nov 21
CAD 279
CAD 650
71%
Kelowna Chicago
Air Canada Air Canada
One way
Economy
Fri, Nov 13
CAD 227
CAD 788

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 259) and highest in October (CAD 335).

CAD 335
CAD 297
CAD 259
CAD 221
    Cheapest
  • CAD 335
    Oct
  • CAD 315
    Nov
  • CAD 300
    Dec
  • CAD 259
    Jan
  • CAD 267
    Feb
  • CAD 300
    Mar
  • CAD 298
    Apr
  • CAD 283
    May
  • CAD 290
    Jun
  • CAD 293
    Jul
  • CAD 292
    Aug
  • CAD 276
    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 357) and highest in October (CAD 467).

CAD 467
CAD 412
CAD 357
CAD 302
    Cheapest
  • CAD 467
    Oct
  • CAD 422
    Nov
  • CAD 419
    Dec
  • CAD 380
    Jan
  • CAD 362
    Feb
  • CAD 385
    Mar
  • CAD 378
    Apr
  • CAD 395
    May
  • CAD 391
    Jun
  • CAD 404
    Jul
  • CAD 388
    Aug
  • CAD 357
    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 318
CAD 296
CAD 273
CAD 251
  • CAD 284
    Mon
  • CAD 273
    Tue
  • CAD 288
    Wed
  • CAD 284
    Thu
  • CAD 281
    Fri
  • CAD 290
    Sat
  • CAD 318
    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
Mon, Nov 2- Mon, Nov 9
8 day trip
Toronto
Chicago
CAD 255
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8 day trip
Sat, Dec 5- Sat, Dec 12
8 day trip
Montreal
Chicago
CAD 306
Search
5 day trip
Thu, Dec 10- Mon, Dec 14
5 day trip
Calgary
Chicago
CAD 314
Search
3 day trip
Fri, Oct 30- Sun, Nov 1
3 day trip
Edmonton
Chicago
CAD 382
Search
4 day trip
Fri, Nov 13- Mon, Nov 16
4 day trip
Kelowna
Chicago
CAD 411
Search
8 day trip
Thu, Nov 5- Thu, Nov 12
8 day trip
Vancouver
Chicago
CAD 421
Search
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Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight price CAD 161
Cheapest return ticket price CAD 286
Cheapest month January
Peak season for travel July
Flight distance 701.97km
Average flight time 2 hours 7 minutes
Popular airline Porter 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 November. The average price of flight tickets to Chicago in November is CAD 373.
  • Flight tickets to Chicago are the cheapest in January compared to other months, the average price is CAD 656.
  • 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.