Find cheap flights to Chicago

Round-trip
Economy
Denver (DEN)
Chicago (CHI)
Wed. 2/12
Wed. 9/12
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 April is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around 291 C$. If you don’t want to visit Chicago in April, then you should wait until March to fly from Canada, when ticket prices are also cheap, with an average price of 296 C$.

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

We recommend purchasing flights from Canada to Chicago 46 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 328 C$. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as 239 C$ 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 329 C$. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Monday is 356 C$.

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 314 C$. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are 350 C$ 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 422 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
Air Canada
30 Apr.
YHZ
Halifax Intl
7h 06m
1 stop
ORD
Chicago O'Hare Intl
14 May
ORD
Chicago O'Hare Intl
6h 32m
1 stop
YHZ
Halifax Intl
Multiple Airlines
30 Apr.
YHZ
Halifax Intl
8h 00m
1 stop
ORD
Chicago O'Hare Intl
14 May
ORD
Chicago O'Hare Intl
8h 32m
2 stops
YHZ
Halifax Intl
United Airlines
30 Apr.
YHZ
Halifax Intl
5h 58m
1 stop
ORD
Chicago O'Hare Intl
14 May
ORD
Chicago O'Hare Intl
5h 54m
1 stop
YHZ
Halifax Intl
ANA
5 Jan.
YYZ
Toronto Pearson Intl
1h 41m
ORD
Chicago O'Hare Intl
11 Jan.
ORD
Chicago O'Hare Intl
4h 20m
1 stop
YYZ
Toronto Pearson Intl
American Airlines
11 Jan.
YYZ
Toronto Pearson Intl
2h 12m
ORD
Chicago O'Hare Intl
25 Jan.
ORD
Chicago O'Hare Intl
11h 07m
1 stop
YYZ
Toronto Pearson Intl
Air Canada
9 Feb.
YHZ
Halifax Intl
5h 31m
1 stop
ORD
Chicago O'Hare Intl
11 Feb.
ORD
Chicago O'Hare Intl
5h 44m
1 stop
YHZ
Halifax 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 Air Canada
Cheapest
Best
Quickest
Air Canada
30 Dec.
YOW
Ottawa
6h 44m
1 stop
ORD
Chicago O'Hare Intl
United Airlines
7 Jan.
YYZ
Toronto Pearson Intl
1h 58m
ORD
Chicago O'Hare Intl
American Airlines
30 Dec.
YYZ
Toronto Pearson Intl
2h 08m
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
Halifax to Chicago Flights
Fastest flight time
6h 31m
Cheapest price
241 C$
London to Chicago Flights
Fastest flight time
6h 51m
Cheapest price
248 C$
Toronto to Chicago Flights
Fastest flight time
1h 41m
Cheapest price
282 C$
Québec City to Chicago Flights
Fastest flight time
5h 36m
Cheapest price
337 C$
Ottawa to Chicago Flights
Fastest flight time
4h 31m
Cheapest price
338 C$
Regina to Chicago Flights
Fastest flight time
7h 20m
Cheapest price
377 C$
Victoria to Chicago Flights
Fastest flight time
7h 53m
Cheapest price
378 C$
Vancouver to Chicago Flights
Fastest flight time
4h 00m
Cheapest price
387 C$
Calgary to Chicago Flights
Fastest flight time
3h 19m
Cheapest price
387 C$
Montreal to Chicago Flights
Fastest flight time
2h 30m
Cheapest price
395 C$
Saskatoon to Chicago Flights
Fastest flight time
6h 50m
Cheapest price
411 C$
St. John's to Chicago Flights
Fastest flight time
7h 46m
Cheapest price
413 C$
Kelowna to Chicago Flights
Fastest flight time
8h 05m
Cheapest price
421 C$
Grande Prairie to Chicago Flights
Fastest flight time
6h 30m
Cheapest price
431 C$
Saint John to Chicago Flights
Fastest flight time
5h 40m
Cheapest price
444 C$
Winnipeg to Chicago Flights
Fastest flight time
2h 13m
Cheapest price
465 C$
Sudbury to Chicago Flights
Fastest flight time
5h 28m
Cheapest price
491 C$
Moncton to Chicago Flights
Fastest flight time
6h 16m
Cheapest price
655 C$
Comox to Chicago Flights
Fastest flight time
31h 52m
Cheapest price
923 C$
Deer Lake to Chicago Flights
Fastest flight time
9h 05m
Cheapest price
2,046 C$
View more

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