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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
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 641. Don’t miss out!

34%
Toronto Chicago
Air Canada Air Canada
One way
Economy
Mon, Sep 7
PLN 223
PLN 337
54%
Vancouver Chicago
WestJet WestJet
One way
Economy
Wed, Sep 2
PLN 276
PLN 594
67%
Calgary Chicago
WestJet WestJet
One way
Economy
Tue, Sep 1
PLN 182
PLN 548
55%
Montreal Chicago
Air Canada Air Canada
One way
Economy
Thu, Sep 17
PLN 197
PLN 440
66%
Edmonton Chicago
WestJet WestJet
One way
Economy
Wed, Aug 26
PLN 232
PLN 691
63%
Winnipeg Chicago
WestJet WestJet
One way
Economy
Fri, Sep 11
PLN 252
PLN 690
68%
Saskatoon Chicago
WestJet WestJet
One way
Economy
Fri, Sep 11
PLN 230
PLN 727
54%
New York Chicago
Delta Air Lines Delta Air Lines
One way
Economy
Mon, Aug 31
PLN 144
PLN 311
38%
New Delhi Chicago
Etihad Airways Etihad Airways
One way
Economy
Tue, Sep 8
PLN 1,025
PLN 1,666

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 PLN 248. The most expensive month is usually October, with average prices reaching PLN 336.

PLN 336
PLN 292
PLN 248
PLN 204
  • CAD 248
    Jul
  • CAD 294
    Aug
  • CAD 261
    Sep
  • CAD 336
    Oct
  • CAD 312
    Nov
  • CAD 298
    Dec
  • CAD 257
    Jan
  • CAD 265
    Feb
  • CAD 298
    Mar
  • CAD 296
    Apr
  • CAD 281
    May
  • CAD 288
    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 324. October is usually the most expensive period, with prices averaging as high as PLN 456.

PLN 456
PLN 390
PLN 324
PLN 258
    Cheapest
  • CAD 346
    Jul
  • CAD 374
    Aug
  • CAD 324
    Sep
  • CAD 456
    Oct
  • CAD 418
    Nov
  • CAD 416
    Dec
  • CAD 377
    Jan
  • CAD 360
    Feb
  • CAD 382
    Mar
  • CAD 375
    Apr
  • CAD 392
    May
  • CAD 387
    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 315
PLN 290
PLN 264
PLN 239
    Cheapest
  • CAD 284
    Mon
  • CAD 283
    Tue
  • CAD 309
    Wed
  • CAD 281
    Thu
  • CAD 284
    Fri
  • CAD 264
    Sat
  • CAD 315
    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.

4 day trip
Thu, Sep 10- Sun, Sep 13
4 day trip
Toronto
Chicago
PLN 249
Search
4 day trip
Fri, Aug 28- Mon, Aug 31
4 day trip
Calgary
Chicago
PLN 291
Search
4 day trip
Fri, Oct 2- Mon, Oct 5
4 day trip
Vancouver
Chicago
PLN 327
Search
8 day trip
Wed, Aug 26- Wed, Sep 2
8 day trip
Montreal
Chicago
PLN 329
Search
3 day trip
Thu, Aug 13- Sat, Aug 15
3 day trip
Halifax
Chicago
PLN 383
Search
8 day trip
Sun, Oct 11- Sun, Oct 18
8 day trip
Winnipeg
Chicago
PLN 390
Search
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Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight priceCAD 156
Cheapest return ticket priceCAD 251
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 September. The average price of flight tickets to Chicago in September is CAD 331.
  • Flight tickets to Chicago are the cheapest in October compared to other months, the average price is CAD 674.
  • 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.