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Cheapest flights to Chicago airports
Find the cheapest flights to these Chicago airports from your nearest city or 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 AIRPORT | April | 15% cheaper | Flying 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 AIRPORT | October | 17% more expensive | It 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 AIRPORT | October | 269% more users visited | More 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
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
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
More flights to Chicago
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Start planning your trip to Chicago
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