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
Toronto Pearson Intl Airport
Chicago Midway Airport

CHEAPEST ROUTE FROM Toronto TO Chicago

Toronto Island Airport (YTZ) to Chicago Midway Airport (MDW)

Typically, flights to Chicago from Toronto are cheaper when flying from Toronto Island to Chicago Midway, which has an average price of C$ 312

CHEAPEST MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTApril15% cheaperFlying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 283 in April
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTOctober17% more expensiveIt costs about C$ 391 for flights to Chicago from Toronto Pearson Intl Airport in October
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTOctober269% more users visitedMore momondo users searched in flights to Chicago from Toronto Pearson 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 Las Vegas found flights 88% 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 C$ 287.

  • 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 C$ 318. Don’t hesitate to check prices now though, because momondo users recently found tickets for as low as C$ 187.

  • 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 C$ 320. 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 C$ 347. 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 C$ 317. 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 C$ 348 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 C$ 437 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.

  • Are there flights to Logan Square?

    Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Logan Square (15.4 km away).

  • What’s the closest airport to Magnificent Mile?

    The closest airport to Magnificent Mile is Chicago Midway, 15.7 km away.


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
Porter Airlines
11 Mar.
YTZ4:00 a.m.Toronto Island
1h 50m
MDW5:50 a.m.Chicago Midway
21 Mar.
MDW6:35 a.m.Chicago Midway
1h 37m
YTZ8:12 a.m.Toronto Island
Porter Airlines
25 Feb.
YTZ9:45 a.m.Toronto Island
1h 50m
MDW11:35 a.m.Chicago Midway
28 Feb.
MDW11:20 a.m.Chicago Midway
1h 37m
YTZ12:57 p.m.Toronto Island
Porter Airlines
11 Mar.
YTZ4:00 a.m.Toronto Island
1h 50m
MDW5:50 a.m.Chicago Midway
20 Mar.
MDW7:50 a.m.Chicago Midway
1h 37m
YTZ9:27 a.m.Toronto Island
Porter Airlines
21 Mar.
YTZ5:00 a.m.Toronto Island
1h 50m
MDW6:50 a.m.Chicago Midway
27 Mar.
MDW1:15 p.m.Chicago Midway
1h 37m
YTZ2:52 p.m.Toronto Island
Porter Airlines
13 Apr.
YTZ11:55 a.m.Toronto Island
1h 50m
MDW1:45 p.m.Chicago Midway
17 Apr.
MDW1:20 p.m.Chicago Midway
1h 37m
YTZ2:57 p.m.Toronto Island
Porter Airlines
22 Apr.
YTZ2:10 p.m.Toronto Island
1h 50m
MDW4:00 p.m.Chicago Midway
27 Apr.
MDW6:30 a.m.Chicago Midway
1h 37m
YTZ8:07 a.m.Toronto Island

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 and Flair Airlines
Flair Airlines
9 Jun.
YYZ2:50 a.m.Toronto Pearson Intl
1h 50m
ORD4:40 a.m.Chicago O'Hare Intl
Flair Airlines
28 May
YYZ2:50 a.m.Toronto Pearson Intl
1h 50m
ORD4:40 a.m.Chicago O'Hare Intl
Air Canada
18 Apr.
YYZ3:30 p.m.Toronto Pearson Intl
1h 50m
ORD5:20 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
  • Which airlines fly to Chicago?

    When flying to Chicago from Canada, momondo travellers will most often fly with one of these popular airlines: Air Canada, United Airlines, American Airlines or Porter Airlines. Depending on what airport in Canada you fly from, you may be able to find flights with any of these popular airlines.


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 41m
Cheapest priceC$ 204
Montreal to Chicago Flights
Fastest flight time2h 26m
Cheapest priceC$ 294
Vancouver to Chicago Flights
Fastest flight time3h 59m
Cheapest priceC$ 419
Calgary to Chicago Flights
Fastest flight time3h 19m
Cheapest priceC$ 450
Ottawa to Chicago Flights
Fastest flight time4h 50m
Cheapest priceC$ 308
Kelowna to Chicago Flights
Fastest flight time7h 53m
Cheapest priceC$ 442
Edmonton to Chicago Flights
Fastest flight time7h 10m
Cheapest priceC$ 377
Winnipeg to Chicago Flights
Fastest flight time8h 41m
Cheapest priceC$ 450
Seattle to Chicago Flights
Fastest flight time3h 51m
Cheapest priceC$ 223
Regina to Chicago Flights
Fastest flight time8h 48m
Cheapest priceC$ 552
Los Angeles to Chicago Flights
Fastest flight time4h 05m
Cheapest priceC$ 87
Halifax to Chicago Flights
Fastest flight time5h 26m
Cheapest priceC$ 400
Québec City to Chicago Flights
Fastest flight time6h 15m
Cheapest priceC$ 328
Moncton to Chicago Flights
Fastest flight time5h 25m
Cheapest priceC$ 536
Nanaimo to Chicago Flights
Fastest flight time11h 33m
Cheapest priceC$ 1,239
Grande Prairie to Chicago Flights
Fastest flight time15h 07m
Cheapest priceC$ 761
St. John's to Chicago Flights
Fastest flight time10h 47m
Cheapest priceC$ 546
Saskatoon to Chicago Flights
Fastest flight time11h 55m
Cheapest priceC$ 537
Fort McMurray to Chicago Flights
Fastest flight time15h 59m
Cheapest priceC$ 726
London, Ontario to Chicago Flights
Fastest flight time4h 41m
Cheapest priceC$ 493

Start planning your trip to Chicago