Find cheap flights to Chicago

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Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
Vancouver Intl Airport
Milwaukee

CHEAPEST ROUTE FROM Vancouver TO Chicago

Vancouver Intl Airport (YVR) to Milwaukee (MKE)

Typically, flights to Chicago from Vancouver are cheaper when flying from Vancouver Intl to Milwaukee Milwaukee-Mitchell, which has an average price of 396 C$

CHEAPEST MONTH TO FLY TO CHICAGO FROM VANCOUVER INTL AIRPORTSeptember13% cheaperFlying from Vancouver Intl Airport to Chicago costs on average just 480 C$ in September
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM VANCOUVER INTL AIRPORTDecember15% more expensiveIt costs about 634 C$ for flights to Chicago from Vancouver Intl Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM VANCOUVER INTL AIRPORTOctober280% more users visitedMore momondo users searched in flights to Chicago from Vancouver Intl Airport in October than any other month

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 73% 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 March is another great option to travel to Chicago, with average flight prices from Canada averaging around 286 C$.

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

    The best time to book a flight to Chicago from Canada is 46 days out, which is when prices tend to be around 317 C$.

  • 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 319 C$. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around 346 C$. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

    At noon is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as 316 C$. Flying to Chicago at noon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Chicago, so prices are often more expensive at around 347 C$ per ticket.

  • Is there a good place to hike near Chicago?

    Hikers looking for a more family-friendly day in the great outdoors would be best suited to plan their flight to Chicago for September and October, when they can visit Grant Park and enjoy all that the park has to offer.

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

    The best time to plan to fly to Chicago to go sightseeing would be when the temperature is not unbearable and the chance of rain is only moderate. Considering those guidelines, May or June seem like the best times of year to plan your visit.

  • 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 397 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
American Airlines
20 Nov.
YYZ2:45 a.m.Toronto Pearson Intl
2h 09m
ORD4:54 a.m.Chicago O'Hare Intl
4 Dec.
ORD1:38 p.m.Chicago O'Hare Intl
1h 39m
YYZ3:17 p.m.Toronto Pearson Intl
United Airlines
20 Sep.
YYZ10:30 a.m.Toronto Pearson Intl
3h 15m
1 stop
ORD1:45 p.m.Chicago O'Hare Intl
29 Sep.
ORD4:40 a.m.Chicago O'Hare Intl
1h 35m
YYZ6:15 a.m.Toronto Pearson Intl
Air Canada
20 Nov.
YYZ9:00 a.m.Toronto Pearson Intl
5h 30m
1 stop
ORD2:30 p.m.Chicago O'Hare Intl
4 Dec.
ORD7:25 a.m.Chicago O'Hare Intl
1h 37m
YYZ9:02 a.m.Toronto Pearson Intl
American Airlines
29 Oct.
YYZ3:59 p.m.Toronto Pearson Intl
1h 59m
ORD5:58 p.m.Chicago O'Hare Intl
1 Nov.
ORD4:49 a.m.Chicago O'Hare Intl
5h 25m
1 stop
YYZ10:14 a.m.Toronto Pearson Intl
American Airlines
8 Sep.
YYZ12:55 p.m.Toronto Pearson Intl
2h 05m
ORD3:00 p.m.Chicago O'Hare Intl
14 Sep.
ORD4:35 a.m.Chicago O'Hare Intl
5h 39m
1 stop
YYZ10:14 a.m.Toronto Pearson Intl
Air Canada
28 Oct.
YYZ10:00 a.m.Toronto Pearson Intl
6h 33m
1 stop
ORD4:33 p.m.Chicago O'Hare Intl
31 Oct.
ORD8:25 a.m.Chicago O'Hare Intl
1h 37m
YYZ10:02 a.m.Toronto Pearson Intl

Find the cheapest one-way flights to Chicago

If you're looking for one-way flights from Canada to Chicago, view some of our deals below provided by Air Canada, American Airlines and Delta
Air Canada
26 Aug.
YYZ2:30 p.m.Toronto Pearson Intl
1h 49m
ORD4:19 p.m.Chicago O'Hare Intl
Air Canada
28 Sep.
YYZ8:00 a.m.Toronto Pearson Intl
1h 50m
ORD9:50 a.m.Chicago O'Hare Intl
American Airlines
8 Sep.
YYZ12:55 p.m.Toronto Pearson Intl
2h 05m
ORD3:00 p.m.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 time1h 47m
Cheapest price345 C$
Ottawa to Chicago Flights
Fastest flight time3h 42m
Cheapest price376 C$
Vancouver to Chicago Flights
Fastest flight time3h 59m
Cheapest price422 C$
Kingston, Ontario to Chicago Flights
Fastest flight time5h 28m
Cheapest price426 C$
Montreal to Chicago Flights
Fastest flight time3h 52m
Cheapest price436 C$
Edmonton to Chicago Flights
Fastest flight time12h 36m
Cheapest price451 C$
Québec City to Chicago Flights
Fastest flight time4h 20m
Cheapest price455 C$
Saint John to Chicago Flights
Fastest flight time6h 12m
Cheapest price468 C$
Halifax to Chicago Flights
Fastest flight time7h 20m
Cheapest price470 C$
Calgary to Chicago Flights
Fastest flight time3h 19m
Cheapest price471 C$
St. John's to Chicago Flights
Fastest flight time11h 29m
Cheapest price476 C$
Winnipeg to Chicago Flights
Fastest flight time2h 13m
Cheapest price511 C$
Victoria to Chicago Flights
Fastest flight time10h 52m
Cheapest price512 C$
Deer Lake to Chicago Flights
Fastest flight time6h 26m
Cheapest price515 C$
Regina to Chicago Flights
Fastest flight time6h 40m
Cheapest price517 C$
London, Ontario to Chicago Flights
Fastest flight time4h 20m
Cheapest price588 C$
Sudbury, Ontario to Chicago Flights
Fastest flight time5h 54m
Cheapest price589 C$
Saskatoon to Chicago Flights
Fastest flight time6h 24m
Cheapest price759 C$
Kelowna to Chicago Flights
Fastest flight time15h 31m
Cheapest price877 C$
Grande Prairie to Chicago Flights
Fastest flight time16h 20m
Cheapest price879 C$

Start planning your trip to Chicago