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
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
Air Transat logo Air Transat
Jetblue Airways logo Jetblue Airways
Royal Jordanian logo Royal Jordanian
Aeromexico logo Aeromexico
Alaska Airlines logo Alaska Airlines
EgyptAir logo EgyptAir
Sun Country Airlines logo Sun Country Airlines
Cathay Pacific logo Cathay Pacific
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 PLN 43,330. Don’t miss out!

45%
Toronto Chicago
Air Canada Air Canada
One way
Economy
Mon, Aug 17
PLN 8,494
PLN 15,441
64%
Vancouver Chicago
WestJet WestJet
One way
Economy
Wed, Aug 19
PLN 9,420
PLN 25,895
25%
Calgary Chicago
WestJet WestJet
One way
Economy
Sat, Aug 29
PLN 18,549
PLN 24,781
38%
Montreal Chicago
Porter Airlines Porter Airlines
One way
Economy
Thu, Aug 13
PLN 11,080
PLN 17,904
55%
Edmonton Chicago
WestJet WestJet
One way
Economy
Wed, Aug 26
PLN 13,122
PLN 29,019
61%
Winnipeg Chicago
Flair Airlines Flair Airlines
One way
Economy
Mon, Aug 17
PLN 11,716
PLN 30,393
64%
Saskatoon Chicago
WestJet WestJet
One way
Economy
Wed, Aug 26
PLN 10,073
PLN 27,608
49%
New York Chicago
Delta Air Lines Delta Air Lines
One way
Economy
Tue, Aug 25
PLN 6,607
PLN 12,860
58%
New Delhi Chicago
Etihad Airways Etihad Airways
One way
Economy
Wed, Aug 26
PLN 31,970
PLN 75,300

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 PLN 11,177. The most expensive month is usually October, with average prices reaching PLN 14,619.

PLN 14,619
PLN 12,898
PLN 11,177
PLN 9,456
    Cheapest
  • PHP 14,474
    Jul
  • PHP 12,786
    Aug
  • PHP 11,378
    Sep
  • PHP 14,619
    Oct
  • PHP 13,585
    Nov
  • PHP 12,952
    Dec
  • PHP 11,177
    Jan
  • PHP 11,521
    Feb
  • PHP 12,950
    Mar
  • PHP 12,879
    Apr
  • PHP 12,225
    May
  • PHP 12,527
    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 PLN 14,120. October is usually the most expensive period, with prices averaging as high as PLN 19,863.

PLN 19,863
PLN 16,992
PLN 14,120
PLN 11,249
    Cheapest
  • PHP 15,365
    Jul
  • PHP 16,281
    Aug
  • PHP 14,120
    Sep
  • PHP 19,863
    Oct
  • PHP 18,209
    Nov
  • PHP 18,116
    Dec
  • PHP 16,420
    Jan
  • PHP 15,655
    Feb
  • PHP 16,634
    Mar
  • PHP 16,328
    Apr
  • PHP 17,063
    May
  • PHP 16,872
    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.

PLN 13,853
PLN 12,708
PLN 11,563
PLN 10,418
    Cheapest
  • PHP 12,275
    Mon
  • PHP 12,228
    Tue
  • PHP 13,368
    Wed
  • PHP 12,339
    Thu
  • PHP 12,378
    Fri
  • PHP 11,563
    Sat
  • PHP 13,853
    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, Sep 10- Thu, Sep 17
8 day trip
Toronto
Chicago
PLN 10,373
Search
4 day trip
Sun, Aug 30- Wed, Sep 2
4 day trip
Calgary
Chicago
PLN 12,677
Search
4 day trip
Sun, Oct 4- Wed, Oct 7
4 day trip
Vancouver
Chicago
PLN 14,220
Search
8 day trip
Fri, Aug 28- Fri, Sep 4
8 day trip
Montreal
Chicago
PLN 14,311
Search
3 day trip
Sat, Aug 15- Mon, Aug 17
3 day trip
Halifax
Chicago
PLN 16,661
Search
8 day trip
Tue, Oct 13- Tue, Oct 20
8 day trip
Winnipeg
Chicago
PLN 16,970
Search
View more return flights

Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight pricePHP 6,534
Cheapest return ticket pricePHP 10,318
Cheapest monthJuly
Peak season for travelJuly
Flight distance701.97km
Average flight time2 hours 2 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 PHP 17,723.
  • Flight tickets to Chicago are the cheapest in July compared to other months, the average price is PHP 32,705.
  • 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.