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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
Japan Airlines logo Japan Airlines
Sun Country Airlines logo Sun Country Airlines
Cathay Pacific logo Cathay Pacific
Alaska Airlines logo Alaska Airlines
Aeromexico logo Aeromexico
EgyptAir logo EgyptAir

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 SAR 1,015. Don’t miss out!

56%
Toronto Chicago
Porter Airlines Porter Airlines
One way
Economy
Tue, Sep 15
SAR 153
SAR 351
47%
Vancouver Chicago
WestJet WestJet
One way
Economy
Wed, Sep 2
SAR 314
SAR 597
67%
Calgary Chicago
WestJet WestJet
One way
Economy
Tue, Sep 1
SAR 182
SAR 549
50%
Montreal Chicago
Air Canada Air Canada
One way
Economy
Thu, Sep 17
SAR 196
SAR 392
63%
Edmonton Chicago
WestJet WestJet
One way
Economy
Mon, Aug 24
SAR 233
SAR 630
67%
Winnipeg Chicago
WestJet WestJet
One way
Economy
Thu, Oct 1
SAR 231
SAR 692
69%
Saskatoon Chicago
WestJet WestJet
One way
Economy
Thu, Sep 24
SAR 216
SAR 688
49%
New York Chicago
Delta Air Lines Delta Air Lines
One way
Economy
Mon, Aug 31
SAR 144
SAR 280
58%
New Delhi Chicago
Etihad Airways Etihad Airways
One way
Economy
Tue, Sep 8
SAR 721
SAR 1,736

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 SAR 256. The most expensive month is usually October, with average prices reaching SAR 335.

SAR 335
SAR 296
SAR 256
SAR 217
    Cheapest
  • CAD 293
    Aug
  • CAD 261
    Sep
  • CAD 335
    Oct
  • CAD 312
    Nov
  • CAD 297
    Dec
  • CAD 256
    Jan
  • CAD 264
    Feb
  • CAD 297
    Mar
  • CAD 295
    Apr
  • CAD 280
    May
  • CAD 287
    Jun
  • CAD 290
    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, September is often the cheapest month for fly from Toronto to Chicago, with an average price of SAR 324. October is usually the most expensive period, with prices averaging as high as SAR 455.

SAR 455
SAR 390
SAR 324
SAR 259
    Cheapest
  • CAD 363
    Aug
  • CAD 324
    Sep
  • CAD 455
    Oct
  • CAD 417
    Nov
  • CAD 415
    Dec
  • CAD 376
    Jan
  • CAD 359
    Feb
  • CAD 381
    Mar
  • CAD 374
    Apr
  • CAD 391
    May
  • CAD 387
    Jun
  • CAD 400
    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.

SAR 317
SAR 292
SAR 267
SAR 242
    Cheapest
  • CAD 282
    Mon
  • CAD 282
    Tue
  • CAD 306
    Wed
  • CAD 283
    Thu
  • CAD 284
    Fri
  • CAD 267
    Sat
  • CAD 317
    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
SAR 225
Search
4 day trip
Fri, Aug 28- Mon, Aug 31
4 day trip
Calgary
Chicago
SAR 291
Search
4 day trip
Fri, Oct 2- Mon, Oct 5
4 day trip
Vancouver
Chicago
SAR 326
Search
8 day trip
Wed, Aug 26- Wed, Sep 2
8 day trip
Montreal
Chicago
SAR 328
Search
3 day trip
Thu, Aug 13- Sat, Aug 15
3 day trip
Halifax
Chicago
SAR 382
Search
8 day trip
Sun, Oct 11- Sun, Oct 18
8 day trip
Winnipeg
Chicago
SAR 389
Search
View more return flights

Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight priceCAD 144
Cheapest return ticket priceCAD 237
Cheapest monthOctober
Peak season for travelJuly
Flight distance701.97km
Average flight time2 hours 3 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 CAD 520.
  • Flight tickets to Chicago are the cheapest in October compared to other months, the average price is CAD 255.
  • 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.