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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
American Airlines logo American Airlines
WestJet logo WestJet
Delta Air Lines logo Delta Air Lines
Etihad Airways logo Etihad Airways
Frontier Airlines logo Frontier Airlines
Jetblue Airways logo Jetblue Airways
Royal Jordanian logo Royal Jordanian
Air Transat logo Air Transat
Aeromexico logo Aeromexico
Sun Country Airlines logo Sun Country Airlines
Cathay Pacific logo Cathay Pacific
EgyptAir logo EgyptAir
avianca logo avianca
Alaska Airlines logo Alaska Airlines
Japan Airlines logo Japan 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 HK$1,060. Don’t miss out!

54%
Toronto Chicago
Porter Airlines Porter Airlines
One way
Economy
Sat, Sep 5
HK$157
HK$342
63%
Vancouver Chicago
WestJet WestJet
One way
Economy
Thu, Sep 10
HK$220
HK$595
30%
Calgary Chicago
WestJet WestJet
One way
Economy
Tue, Sep 1
HK$356
HK$510
49%
Montreal Chicago
Air Canada Air Canada
One way
Economy
Thu, Sep 17
HK$195
HK$386
-26%
Edmonton Chicago
WestJet WestJet
One way
Economy
Mon, Aug 24
HK$802
HK$637
60%
Winnipeg Chicago
WestJet WestJet
One way
Economy
Thu, Oct 1
HK$229
HK$577
67%
Saskatoon Chicago
WestJet WestJet
One way
Economy
Thu, Sep 24
HK$214
HK$654
61%
New Delhi Chicago
Etihad Airways Etihad Airways
One way
Economy
Mon, Sep 21
HK$691
HK$1,751

When is the cheapest time to book flights to Chicago?

Departure:

What is the cheapest month for one-way flights from Toronto to Chicago?

The average one way ticket price paid by Trip.com users from Toronto to Chicago in each month over the past 12 months.

Based on Trip.com data, the cheapest month to fly from Toronto to Chicago is January, with an average price of HK$254. The most expensive month is usually October, with average prices reaching HK$332.

HK$332
HK$293
HK$254
HK$215
    Cheapest
  • CAD 301
    Aug
  • CAD 259
    Sep
  • CAD 332
    Oct
  • CAD 309
    Nov
  • CAD 295
    Dec
  • CAD 254
    Jan
  • CAD 262
    Feb
  • CAD 294
    Mar
  • CAD 293
    Apr
  • CAD 278
    May
  • CAD 285
    Jun
  • CAD 288
    Jul

What is the cheapest month for return flights from Toronto to Chicago?

Average price of return flights from Toronto to Chicago purchased by Trip.com users by month over the past 12 months

Based on Trip.com's historical data, August is often the cheapest month for fly from Toronto to Chicago, with an average price of HK$317. October is usually the most expensive period, with prices averaging as high as HK$451.

HK$451
HK$384
HK$317
HK$250
  • CAD 317
    Aug
  • CAD 321
    Sep
  • CAD 451
    Oct
  • CAD 414
    Nov
  • CAD 412
    Dec
  • CAD 373
    Jan
  • CAD 356
    Feb
  • CAD 378
    Mar
  • CAD 371
    Apr
  • CAD 388
    May
  • CAD 383
    Jun
  • CAD 396
    Jul

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 Saturday. 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.

HK$314
HK$290
HK$265
HK$241
    Cheapest
  • CAD 280
    Mon
  • CAD 277
    Tue
  • CAD 305
    Wed
  • CAD 285
    Thu
  • CAD 285
    Fri
  • CAD 265
    Sat
  • CAD 314
    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, Sep 14- Mon, Sep 21
8 day trip
Toronto
Chicago
HK$223
Search
4 day trip
Mon, Sep 7- Thu, Sep 10
4 day trip
Vancouver
Chicago
HK$318
Search
8 day trip
Wed, Aug 26- Wed, Sep 2
8 day trip
Montreal
Chicago
HK$325
Search
8 day trip
Sun, Oct 11- Sun, Oct 18
8 day trip
Winnipeg
Chicago
HK$386
Search
8 day trip
Tue, Sep 15- Tue, Sep 22
8 day trip
Kelowna
Chicago
HK$394
Search
4 day trip
Fri, Aug 28- Mon, Aug 31
4 day trip
Calgary
Chicago
HK$471
Search
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Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight priceCAD 150
Cheapest return ticket priceCAD 235
Cheapest monthOctober
Peak season for travelJuly
Flight distance701.97km
Average flight time2 hours 4 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 September. The average price of flight tickets to Chicago in September is CAD 416.
  • Flight tickets to Chicago are the cheapest in October compared to other months, the average price is CAD 351.
  • 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.