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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
American Airlines logo American Airlines
United Airlines logo United Airlines
WestJet logo WestJet
Delta Air Lines logo Delta Air Lines
Frontier Airlines logo Frontier Airlines
Air Transat logo Air Transat
Etihad Airways logo Etihad Airways
Jetblue Airways logo Jetblue Airways
Royal Jordanian logo Royal Jordanian
Philippine Airlines logo Philippine Airlines
Volaris logo Volaris
Japan Airlines logo Japan Airlines
Cathay Pacific logo Cathay Pacific
Alaska Airlines logo Alaska Airlines
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 TWD 9,769. Don’t miss out!

49%
Toronto Chicago
Porter Airlines Porter Airlines
One way
Economy
Thu, Jul 30
TWD 3,740
TWD 7,285
60%
Vancouver Chicago
WestJet WestJet
One way
Economy
Wed, Aug 26
TWD 4,493
TWD 11,096
3%
Calgary Chicago
Air Canada Air Canada
One way
Economy
Wed, Jul 15
TWD 10,829
TWD 11,137
15%
Montreal Chicago
Porter Airlines Porter Airlines
One way
Economy
Wed, Jul 15
TWD 7,199
TWD 8,417
57%
Edmonton Chicago
WestJet WestJet
One way
Economy
Wed, Aug 26
TWD 5,877
TWD 13,651
64%
Saskatoon Chicago
WestJet WestJet
One way
Economy
Sun, Sep 6
TWD 5,251
TWD 14,461
54%
Winnipeg Chicago
Porter Airlines Porter Airlines
One way
Economy
Sun, Jul 26
TWD 6,000
TWD 13,102
44%
New York Chicago
Delta Air Lines Delta Air Lines
One way
Economy
Tue, Aug 4
TWD 3,820
TWD 6,831
30%
New Delhi Chicago
Etihad Airways Etihad Airways
One way
Economy
Thu, Jul 23
TWD 23,165
TWD 32,934

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 July, with an average price of TWD 5,481. The most expensive month is usually October, with average prices reaching TWD 7,635.

TWD 7,635
TWD 6,558
TWD 5,481
TWD 4,404
  • TWD 5,481
    Jul
  • TWD 6,678
    Aug
  • TWD 5,943
    Sep
  • TWD 7,635
    Oct
  • TWD 7,095
    Nov
  • TWD 6,765
    Dec
  • TWD 5,837
    Jan
  • TWD 6,017
    Feb
  • TWD 6,763
    Mar
  • TWD 6,726
    Apr
  • TWD 6,385
    May
  • TWD 6,542
    Jun

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 TWD 7,375. October is usually the most expensive period, with prices averaging as high as TWD 10,374.

TWD 10,374
TWD 8,875
TWD 7,375
TWD 5,876
    Cheapest
  • TWD 7,710
    Jul
  • TWD 8,503
    Aug
  • TWD 7,375
    Sep
  • TWD 10,374
    Oct
  • TWD 9,510
    Nov
  • TWD 9,461
    Dec
  • TWD 8,576
    Jan
  • TWD 8,176
    Feb
  • TWD 8,687
    Mar
  • TWD 8,528
    Apr
  • TWD 8,911
    May
  • TWD 8,812
    Jun

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.

TWD 7,181
TWD 6,589
TWD 5,996
TWD 5,404
    Cheapest
  • TWD 6,475
    Mon
  • TWD 6,431
    Tue
  • TWD 6,739
    Wed
  • TWD 6,319
    Thu
  • TWD 6,435
    Fri
  • TWD 5,996
    Sat
  • TWD 7,181
    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
Wed, Jul 22- Sun, Jul 26
5 day trip
Calgary
Chicago
TWD 7,536
Search
2 day trip
Thu, Sep 10- Fri, Sep 11
2 day trip
Montreal
Chicago
TWD 7,754
Search
6 day trip
Thu, Oct 1- Tue, Oct 6
6 day trip
Vancouver
Chicago
TWD 8,683
Search
2 day trip
Sat, Sep 12- Sun, Sep 13
2 day trip
Halifax
Chicago
TWD 9,299
Search
4 day trip
Fri, Oct 2- Mon, Oct 5
4 day trip
Winnipeg
Chicago
TWD 9,626
Search
4 day trip
Mon, Jul 20- Thu, Jul 23
4 day trip
Toronto
Chicago
TWD 10,318
Search
View more return flights

Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight priceTWD 3,536
Cheapest return ticket priceTWD 5,839
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 August. The average price of flight tickets to Chicago in August is TWD 9,156.
  • Flight tickets to Chicago are the cheapest in October compared to other months, the average price is TWD 8,540.
  • 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.