Find cheap flights to Chicago

Find cheap flights to Chicago

Round-trip
Economy
Washington (WAS)
Chicago All airports
Fri. 3/7
Fri. 10/7
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

Good to know

Low season

March Best time to beat the crowds (2% less expensive on average)

High season

December Most popular time to fly (6% more expensive on average)

Average price of a round-trip

C$ 362 (avg. price over the last 2 weeks)

Good deal for a round-trip

C$ 246 or less

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Toronto C$ 309, from Montreal C$ 380, from Vancouver C$ 412
  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be July, August and September. The cheapest month to fly to Chicago is January.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
  • If you’re interested in flights to Chicago, there are three primary airports that you can fly into. While Chicago Midway International Airport is most convenient for travelers that will be staying in the city center, O'Hare International Airport services the highest number of flights. Chicago Rockford International Airport is a practical choice for individuals staying in the suburbs.
  • For those that would like a direct flight to Chicago, there are several airlines that you can choose from. While American and Porter Airlines are known for having affordable flights and comfortable chairs, United Airlines provides travelers with above-average legroom.
  • To unwind after a long day of traveling, stop by the yoga room in Chicago Midway International Airport. Located in Concourse C, this room provides travelers with complimentary mats and DVD footage of popular yoga positions. It is open 7 days a week from 6 AM to 10 PM.
  • Traveling with your family? Chicago Midway International Airport has a large baby care room that contains a sink, a private nursing area and change tables, making it a convenient place to tend to your child after your flight has landed.
  • If you would like to freshen up after a long day of traveling, purchase an access pass to either the Hilton Athletic Club, Airlines Admirals Club or United Club in O'Hare International Airport in order to access their private showers. Each of these locations provides complimentary towels and toiletries, so you will have everything you need.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Chicago flights

How long is the flight to Chicago?

What is the cheapest flight to Chicago?

Which airlines fly to Chicago?

Which Chicago airport is closest to central Chicago?

What hotels are near Rockford International Airport?

What is the best way to travel from O'Hare International Airport to downtown Chicago?

Does O'Hare International Airport have a prayer room?

What shopping options are there at O'Hare International Airport?

How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?

Top 5 airlines flying to Chicago

Scores according to KAYAK customer reviews

8.7
Japan Airlines
Overall score based on 4,471 reviews
8.9
Boarding
8.6
Comfort
9.1
Crew
8.6
Entertainment
8.5
Food
Airline reviews
Read more about Japan Airlines

Book Cheap Chicago Plane Tickets (Round-trip)

Airports
Origin
Vancouver
C$ 262
only
C$ 262
Edmonton
C$ 367
only
C$ 367
Ottawa
C$ 381
only
C$ 381
Montreal
C$ 392
only
C$ 392
Toronto
C$ 255
only
C$ 255
C$ 261
only
C$ 261
Destination
Chicago
C$ 255
only
C$ 255
C$ 261
only
C$ 261
Fri., 25 Sep.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 55m
Sun., 27 Sep.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
1h 38m
C$ 255
Trip: 3 days
Based on null reviews
Tue., 20 Oct.
YTZ
Toronto Island
MDW
Chicago Midway Airport
1h 47m
Wed., 4 Nov.
MDW
Chicago Midway Airport
YTZ
Toronto Island
1h 37m
C$ 261
Trip: 16 days
Based on null reviews
Tue., 3 Nov.
YVR
Vancouver Airport
ORD
Chicago O'Hare Airport
8h 38m
Wed., 2 Dec.
ORD
Chicago O'Hare Airport
YVR
Vancouver Airport
8h 41m
C$ 262
Trip: 30 days
Based on null reviews
Mon., 16 Nov.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 53m
Tue., 17 Nov.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
1h 40m
C$ 262
Trip: 2 days
Based on null reviews
Fri., 18 Sep.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 55m
Sun., 20 Sep.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
1h 38m
C$ 265
Trip: 3 days
Based on null reviews
Thu., 13 Aug.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 53m
Sun., 23 Aug.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
1h 34m
C$ 267
Trip: 11 days
Based on null reviews
Fri., 18 Sep.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 55m
Sun., 20 Sep.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
4h 45m
C$ 269
Trip: 3 days
Based on null reviews
Thu., 2 Jul.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 55m
Thu., 16 Jul.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
12h 30m
C$ 273
Trip: 15 days
Based on null reviews
Tue., 3 Nov.
YVR
Vancouver Airport
ORD
Chicago O'Hare Airport
8h 13m
Wed., 2 Dec.
ORD
Chicago O'Hare Airport
YVR
Vancouver Airport
8h 28m
C$ 296
Trip: 30 days
Based on null reviews
Fri., 17 Jul.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 57m
Mon., 20 Jul.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
1h 38m
C$ 308
Trip: 4 days
Based on null reviews
Tue., 7 Jul.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 50m
Tue., 21 Jul.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
1h 38m
C$ 310
Trip: 15 days
Based on null reviews
Mon., 6 Jul.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 55m
Mon., 13 Jul.
ORD
Chicago O'Hare Airport
YYZ
Toronto Pearson Airport
1h 39m
C$ 315
Trip: 8 days
Based on null reviews
Sun., 13 Sep.
YEG
Edmonton
ORD
Chicago O'Hare Airport
8h 41m
Thu., 17 Sep.
ORD
Chicago O'Hare Airport
YEG
Edmonton
8h 25m
C$ 367
Trip: 5 days
Based on null reviews
Fri., 10 Jul.
YEG
Edmonton
ORD
Chicago O'Hare Airport
7h 15m
Wed., 15 Jul.
ORD
Chicago O'Hare Airport
YEG
Edmonton
7h 57m
C$ 372
Trip: 6 days
Based on null reviews
Fri., 23 Oct.
YOW
Ottawa Airport
ORD
Chicago O'Hare Airport
4h 43m
Mon., 26 Oct.
ORD
Chicago O'Hare Airport
YOW
Ottawa Airport
6h 52m
C$ 381
Trip: 4 days
Based on null reviews
Fri., 23 Oct.
YOW
Ottawa Airport
ORD
Chicago O'Hare Airport
5h 24m
Mon., 26 Oct.
ORD
Chicago O'Hare Airport
YOW
Ottawa Airport
1h 54m
C$ 384
Trip: 4 days
Based on null reviews
Fri., 4 Sep.
YUL
Montreal Trudeau Airport
ORD
Chicago O'Hare Airport
5h 33m
Mon., 7 Sep.
ORD
Chicago O'Hare Airport
YUL
Montreal Trudeau Airport
4h 47m
C$ 392
Trip: 4 days
Based on null reviews
Wed., 16 Sep.
YUL
Montreal Trudeau Airport
ORD
Chicago O'Hare Airport
6h 12m
Sun., 20 Sep.
ORD
Chicago O'Hare Airport
YUL
Montreal Trudeau Airport
6h 33m
C$ 399
Trip: 5 days
Based on null reviews
Wed., 5 Aug.
YVR
Vancouver Airport
ORD
Chicago O'Hare Airport
6h 44m
Sun., 16 Aug.
ORD
Chicago O'Hare Airport
YVR
Vancouver Airport
4h 39m
C$ 410
Trip: 12 days
Based on null reviews
Sun., 13 Sep.
YEG
Edmonton
ORD
Chicago O'Hare Airport
7h 34m
Thu., 17 Sep.
ORD
Chicago O'Hare Airport
YEG
Edmonton
16h 06m
C$ 491
Trip: 5 days
Based on null reviews
Show more results

Book Cheap Chicago Plane Tickets (One-way)

Airports
Origin
Vancouver
C$ 159
only
C$ 159
Ottawa
C$ 223
only
C$ 223
Montreal
C$ 182
only
C$ 182
Toronto
C$ 157
only
C$ 157
C$ 152
only
C$ 152
Destination
Chicago
C$ 157
only
C$ 157
C$ 152
only
C$ 152
Wed., 12 Aug.
YTZ
Toronto Island
MDW
Chicago Midway Airport
1h 47m
C$ 152
Based on null reviews
Wed., 12 Aug.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 59m
C$ 157
Based on null reviews
Mon., 7 Sep.
YVR
Vancouver Airport
ORD
Chicago O'Hare Airport
6h 50m
C$ 159
Based on null reviews
Wed., 12 Aug.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 59m
C$ 168
Based on null reviews
Sat., 8 Aug.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
2h 00m
C$ 170
Based on null reviews
Tue., 11 Aug.
YUL
Montreal Trudeau Airport
ORD
Chicago O'Hare Airport
24h 48m
C$ 182
Based on null reviews
Thu., 23 Jul.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 50m
C$ 189
Based on null reviews
Sat., 8 Aug.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
1h 48m
C$ 190
Based on null reviews
Tue., 14 Jul.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
12h 35m
C$ 202
Based on null reviews
Sat., 8 Aug.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
6h 22m
C$ 204
Based on null reviews
Sat., 8 Aug.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
12h 08m
C$ 216
Based on null reviews
Thu., 2 Jul.
YOW
Ottawa Airport
ORD
Chicago O'Hare Airport
6h 10m
C$ 223
Based on null reviews
Mon., 13 Jul.
YUL
Montreal Trudeau Airport
ORD
Chicago O'Hare Airport
2h 35m
C$ 225
Based on null reviews
Thu., 25 Jun.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
5h 11m
C$ 231
Based on null reviews
Sat., 5 Sep.
YVR
Vancouver Airport
ORD
Chicago O'Hare Airport
6h 10m
C$ 244
Based on null reviews
Thu., 2 Jul.
YOW
Ottawa Airport
ORD
Chicago O'Hare Airport
7h 10m
C$ 246
Based on null reviews
Sun., 19 Jul.
YVR
Vancouver Airport
ORD
Chicago O'Hare Airport
19h 56m
C$ 247
Based on null reviews
Tue., 11 Aug.
YVR
Vancouver Airport
ORD
Chicago O'Hare Airport
19h 05m
C$ 250
Based on null reviews
Fri., 26 Jun.
YYZ
Toronto Pearson Airport
ORD
Chicago O'Hare Airport
8h 06m
C$ 251
Based on null reviews
Tue., 11 Aug.
YUL
Montreal Trudeau Airport
ORD
Chicago O'Hare Airport
6h 45m
C$ 273
Based on null reviews
Show more results
*
Prices are per person, are for e–tickets and include all taxes & fees in CAD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First