Cheap Flights to Chicago from CAD 72
Find today's best flight deals, with flights to Chicago from as low as CAD 72!
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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
United Airlines
Air Canada
American Airlines
WestJet
Air India
Delta Air Lines
Southern Airways Express
Jetblue Airways
Southwest Airlines
Cathay Pacific
Etihad Airways
Alaska Airlines
Spirit Airlines
Hawaiian Airlines
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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 CAD 854. Don’t miss out!
53%
Toronto
Chicago
Porter Airlines
One way
Economy
Thu, Jun 26
CAD 138
CAD 291
57%
Calgary
Chicago
United Airlines
One way
Economy
Sat, Jun 14
CAD 145
CAD 332
-78%
Vancouver
Chicago
WestJet
One way
Economy
Wed, Jun 11
CAD 783
CAD 440
43%
Montreal
Chicago
Porter Airlines
One way
Economy
Thu, Jun 26
CAD 267
CAD 465
64%
Edmonton
Chicago
WestJet
One way
Economy
Sat, Jul 5
CAD 148
CAD 406
64%
Winnipeg
Chicago
WestJet
One way
Economy
Mon, Jun 16
CAD 147
CAD 404
75%
Washington D.C.
Chicago
Frontier Airlines
One way
Economy
Fri, Jul 18
CAD 75
CAD 299
57%
Ahmedabad
Chicago
American Airlines
One way
Economy
Thu, Jun 12
CAD 647
CAD 1,501
74%
Seattle
Chicago
Delta Air Lines
One way
Economy
Tue, Jul 22
CAD 72
CAD 277
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, Jun 19
-
Sun, Jun 22
4 Day Trip
Montreal
Chicago
CAD 146
5 Day Trip
Wed, Jul 2
-
Sun, Jul 6
5 Day Trip
Calgary
Chicago
CAD 203
4 Day Trip
Wed, Jun 11
-
Sat, Jun 14
4 Day Trip
Vancouver
Chicago
CAD 206
3 Day Trip
Fri, Jun 20
-
Sun, Jun 22
3 Day Trip
Toronto
Chicago
CAD 223
5 Day Trip
Sun, Jun 29
-
Thu, Jul 3
5 Day Trip
Edmonton
Chicago
CAD 238
7 Day Trip
Wed, Jun 11
-
Tue, Jun 17
7 Day Trip
Regina
Chicago
CAD 246
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Useful info for your flights to Chicago from the United Kingdom
| Cheapest one-way flight price | CAD 106 |
|---|---|
| Cheapest return ticket price | CAD 153 |
| Off-season travel month | April |
| Peak season for travel | March |
| Flight distance | 701.97km |
| Average flight time | 1 hour 56 minutes |
| Popular airline | United Airlines |
| Cheapest month | September |
Frequently asked questions: Booking Chicago flights
-
How long is the flights to Chicago?
- Approx. 1 hour 51 minutes to fly from Toronto to Chicago.
- Approx. 3 hours 39 minutes to fly from Montreal to Chicago.
- Approx. 6 hours 19 minutes to fly from Vancouver to Chicago.
- Approx. 4 hours 30 minutes to fly from Calgary to Chicago.
-
How to get cheapest flights 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.
-
What is the most popular month to visit Chicago?
Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is June. The average price of flight tickets to Chicago in June is CAD 419. -
When are flight to Chicago cheapest?
Flight tickets to Chicago are the cheapest in September compared to other months, the average price is CAD 346. -
What are the major airports in Chicago?
-
Which popular airlines have flights to Chicago?
Popular airlines with flights to Chicago: Frontier Airlines, American Airlines, and United Airlines.