Trip.com
>
Cheap Flights
>
United States
>
Illinois
>
Chicago

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
Air Transat logo Air Transat
Etihad Airways logo Etihad Airways
Frontier Airlines logo Frontier Airlines
Japan Airlines logo Japan Airlines
Alaska Airlines logo Alaska Airlines
Spirit Airlines logo Spirit Airlines
Aer Lingus logo Aer Lingus
Volaris logo Volaris
Philippine Airlines logo Philippine Airlines
Cathay Pacific logo Cathay Pacific
Asiana Airlines logo Asiana 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 KRW 978,000. Don’t miss out!

-11%
Toronto Chicago
Air Canada Air Canada
One way
Economy
Sat, Jun 27
KRW 354,700
KRW 319,400
16%
Vancouver Chicago
WestJet WestJet
One way
Economy
Sat, Jun 13
KRW 464,900
KRW 550,400
-5%
Calgary Chicago
Air Canada Air Canada
One way
Economy
Wed, Jul 15
KRW 600,400
KRW 574,400
54%
Montreal Chicago
Air Canada Air Canada
One way
Economy
Sat, Jun 13
KRW 190,000
KRW 412,000
57%
Edmonton Chicago
United Airlines United Airlines
One way
Economy
Sat, Jun 13
KRW 268,400
KRW 603,600
48%
Saskatoon Chicago
Air Canada Air Canada
One way
Economy
Thu, Jun 25
KRW 304,400
KRW 590,600
58%
Winnipeg Chicago
WestJet WestJet
One way
Economy
Sat, Jun 13
KRW 251,100
KRW 600,900
56%
Regina Chicago
WestJet WestJet
One way
Economy
Tue, Jun 23
KRW 242,100
KRW 540,700
60%
New Delhi Chicago
Etihad Airways Etihad Airways
One way
Economy
Sat, Jun 13
KRW 653,500
KRW 1,631,500

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 June, with an average price of KRW 245,300. The most expensive month is usually October, with average prices reaching KRW 362,100.

KRW 362,100
KRW 303,700
KRW 245,300
KRW 186,900
  • KRW 245,300
    Jun
  • KRW 265,200
    Jul
  • KRW 316,700
    Aug
  • KRW 281,900
    Sep
  • KRW 362,100
    Oct
  • KRW 336,500
    Nov
  • KRW 320,900
    Dec
  • KRW 276,900
    Jan
  • KRW 285,400
    Feb
  • KRW 320,800
    Mar
  • KRW 319,000
    Apr
  • KRW 302,800
    May

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, September is often the cheapest month for fly from Toronto to Chicago, with an average price of KRW 349,800. October is usually the most expensive period, with prices averaging as high as KRW 492,000.

KRW 492,000
KRW 420,900
KRW 349,800
KRW 278,700
    Cheapest
  • KRW 381,000
    Jun
  • KRW 376,900
    Jul
  • KRW 403,300
    Aug
  • KRW 349,800
    Sep
  • KRW 492,000
    Oct
  • KRW 451,100
    Nov
  • KRW 448,800
    Dec
  • KRW 406,800
    Jan
  • KRW 387,800
    Feb
  • KRW 412,100
    Mar
  • KRW 404,500
    Apr
  • KRW 422,700
    May

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.

KRW 320,100
KRW 303,550
KRW 287,000
KRW 270,450
    Cheapest
  • KRW 296,700
    Mon
  • KRW 298,900
    Tue
  • KRW 313,200
    Wed
  • KRW 291,600
    Thu
  • KRW 315,400
    Fri
  • KRW 287,000
    Sat
  • KRW 320,100
    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.

5 day trip
Fri, Jul 3- Tue, Jul 7
5 day trip
Toronto
Chicago
KRW 300,800
Search
4 day trip
Fri, Jun 12- Mon, Jun 15
4 day trip
Montreal
Chicago
KRW 319,000
Search
5 day trip
Wed, Jul 22- Sun, Jul 26
5 day trip
Calgary
Chicago
KRW 357,400
Search
2 day trip
Fri, Jun 19- Sat, Jun 20
2 day trip
Edmonton
Chicago
KRW 425,800
Search
4 day trip
Fri, Jun 12- Mon, Jun 15
4 day trip
Vancouver
Chicago
KRW 429,100
Search
4 day trip
Fri, Jun 19- Mon, Jun 22
4 day trip
Ottawa
Chicago
KRW 515,700
Search
View more return flights

Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight priceKRW 169,500
Cheapest return ticket priceKRW 277,000
Cheapest monthSeptember
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 July. The average price of flight tickets to Chicago in July is KRW 618,400.
  • Flight tickets to Chicago are the cheapest in September compared to other months, the average price is KRW 329,600.
  • Popular airlines with flights to Chicago: American Airlines, United Airlines, and Frontier Airlines.

Find Cheap Flights with Trip.com

Show more

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.