Find cheap flights to Chicago

Round-trip
Economy
Wichita (ICT)
Chicago (CHI)
Sun. 20/9
Sun. 27/9
Any month
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Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
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When is the best time to fly to Chicago?

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Minneapolis found flights 74% cheaper than the average price of flights to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around 289 C$. If you don’t want to visit Chicago in February, then you should wait until March to fly from Canada, when ticket prices are also cheap, with an average price of 300 C$.

How far in advance should I book a flight to Chicago?

We recommend purchasing flights from Canada to Chicago 60 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago for 329 C$. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as 231 C$ on momondo.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as 334 C$. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Monday is 361 C$.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Canada to Chicago during this time can be as low as 318 C$. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are 355 C$ on average. Flights to Chicago from Canada in the evening are generally more expensive because this time of day is more convenient for travellers’ schedules.

Is there a good place to hike near Chicago?

If you’re looking to do your hiking in warmer conditions, consider planning your flight to Chicago for September and October. Parks like Grant Park are popular hot spots in those months.

When is it best to fly to Chicago to go sightseeing?

Sights like Magnificent Mile, Grant Park, and Chicago Theater are most enjoyable in months with moderate weather conditions like May or June. Plan your flight to Chicago for those months.

Is there an alternative airport near Chicago?

Those flying to Chicago could potentially find better pricing at Chicago O'Hare Intl Airport (26 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre) depending on the month and departure airport.

Is there a cheaper alternative to flying into Chicago?

Chicago Midway Airport has an average price of 428 C$ per person and is typically the cheapest airport to fly into when visiting Chicago. This average price does vary based on departure city. Try momondo’s Airport-to-Airport Pricing Tool to find the cheapest flight.


Chicago flight deals found on momondo

Check out some of the best fares from airports in Canada to Chicago found recently by users on momondo
Cheapest
Best
Quickest
Qantas Airways
15 Oct.
YYZ
Toronto Pearson Intl
1h 52m
ORD
Chicago O'Hare Intl
4 Feb.
ORD
Chicago O'Hare Intl
1h 40m
YYZ
Toronto Pearson Intl
Air New Zealand
15 Oct.
YYZ
Toronto Pearson Intl
1h 58m
ORD
Chicago O'Hare Intl
4 Feb.
ORD
Chicago O'Hare Intl
1h 32m
YYZ
Toronto Pearson Intl
Lufthansa
15 Oct.
YYZ
Toronto Pearson Intl
1h 58m
ORD
Chicago O'Hare Intl
4 Feb.
ORD
Chicago O'Hare Intl
4h 14m
1 stop
YYZ
Toronto Pearson Intl
Multiple Airlines
15 Oct.
YYZ
Toronto Pearson Intl
1h 58m
ORD
Chicago O'Hare Intl
4 Feb.
ORD
Chicago O'Hare Intl
4h 49m
1 stop
YYZ
Toronto Pearson Intl
Porter Airlines
23 Nov.
YTZ
Toronto Island
1h 50m
MDW
Chicago Midway
9 Dec.
MDW
Chicago Midway
1h 37m
YTZ
Toronto Island
British Airways
16 Oct.
YYZ
Toronto Pearson Intl
1h 52m
ORD
Chicago O'Hare Intl
19 Oct.
ORD
Chicago O'Hare Intl
5h 35m
1 stop
YYZ
Toronto Pearson Intl

Find the cheapest one-way flights to Chicago

If you're looking for one-way flights to Chicago, view some of our deals below provided by British Airways
Cheapest
Best
Quickest
British Airways
10 Oct.
YYZ
Toronto Pearson Intl
1h 52m
ORD
Chicago O'Hare Intl
Delta
15 Oct.
YYZ
Toronto Pearson Intl
4h 57m
1 stop
ORD
Chicago O'Hare Intl
Multiple Airlines
13 Nov.
YYZ
Toronto Pearson Intl
29h 39m
1 stop
ORD
Chicago O'Hare Intl

Which airlines fly to Chicago?

Here you can see a selection of the most popular and cheapest airlines for flights to Chicago

Airports near Chicago

Below you will find all the airports in Chicago along with their distance from the city centre

Popular routes to Chicago

Most frequently searched flights to Chicago along with the cheapest price and shortest flight duration
Toronto to Chicago Flights
Fastest flight time
1h 46m
Cheapest price
247 C$
Vancouver to Chicago Flights
Fastest flight time
3h 59m
Cheapest price
250 C$
London to Chicago Flights
Fastest flight time
5h 31m
Cheapest price
269 C$
Ottawa to Chicago Flights
Fastest flight time
2h 11m
Cheapest price
292 C$
Québec City to Chicago Flights
Fastest flight time
4h 31m
Cheapest price
305 C$
Montreal to Chicago Flights
Fastest flight time
2h 28m
Cheapest price
334 C$
Regina to Chicago Flights
Fastest flight time
6h 50m
Cheapest price
342 C$
Halifax to Chicago Flights
Fastest flight time
6h 09m
Cheapest price
350 C$
Moncton to Chicago Flights
Fastest flight time
12h 25m
Cheapest price
376 C$
Calgary to Chicago Flights
Fastest flight time
3h 20m
Cheapest price
400 C$
St. John's to Chicago Flights
Fastest flight time
9h 30m
Cheapest price
423 C$
Fort McMurray to Chicago Flights
Fastest flight time
10h 17m
Cheapest price
425 C$
Kelowna to Chicago Flights
Fastest flight time
9h 13m
Cheapest price
429 C$
Saskatoon to Chicago Flights
Fastest flight time
9h 47m
Cheapest price
442 C$
Winnipeg to Chicago Flights
Fastest flight time
2h 27m
Cheapest price
470 C$
Sudbury to Chicago Flights
Fastest flight time
5h 20m
Cheapest price
592 C$
Deer Lake to Chicago Flights
Fastest flight time
6h 19m
Cheapest price
650 C$
Victoria to Chicago Flights
Fastest flight time
24h 25m
Cheapest price
819 C$
Grande Prairie to Chicago Flights
Fastest flight time
16h 37m
Cheapest price
2,323 C$
Saint John to Chicago Flights
Fastest flight time
18h 45m
Cheapest price
8,393 C$
View more

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