Find cheap flights to Chicago

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Washington (WAS)
Chicago (CHI)
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Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
Seattle
South Bend

CHEAPEST ROUTE FROM Seattle TO Chicago

Seattle (SEA) to Chicago O'Hare Intl Airport (ORD)

Typically, flights to Chicago from Seattle are cheaper when flying from Seattle/Tacoma Intl to Chicago O'Hare Intl, which has an average price of 265 C$

CHEAPEST MONTH TO FLY TO CHICAGO FROM SEATTLEAugust35% cheaperFlying from Seattle to Chicago costs on average just 173 C$ in August
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM SEATTLEDecember39% more expensiveIt costs about 373 C$ for flights to Chicago from Seattle in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM SEATTLEOctober271% more users visitedMore momondo users searched in flights to Chicago from Seattle 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 April is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around 280 C$. If you don’t want to visit Chicago in April, then you should wait until March to fly from Canada, when ticket prices are also cheap, with an average price of 285 C$.

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 316 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 318 C$. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Monday is 345 C$.

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 315 C$. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are 346 C$ 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 395 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
Air Canada
2 May
4:40 a.m.Toronto Pearson Intl
1h 44m
6:24 a.m.Chicago O'Hare Intl
29 May
6:10 a.m.Chicago O'Hare Intl
1h 36m
7:46 a.m.Toronto Pearson Intl
Air Canada
19 May
8:00 a.m.Toronto Pearson Intl
1h 48m
9:48 a.m.Chicago O'Hare Intl
21 May
6:10 a.m.Chicago O'Hare Intl
1h 36m
7:46 a.m.Toronto Pearson Intl
Air Canada
3 May
4:35 a.m.Toronto Pearson Intl
1h 50m
6:25 a.m.Chicago O'Hare Intl
13 May
6:10 a.m.Chicago O'Hare Intl
1h 36m
7:46 a.m.Toronto Pearson Intl
Aer Lingus
16 May
8:00 a.m.Toronto Pearson Intl
1h 48m
9:48 a.m.Chicago O'Hare Intl
23 May
1:50 p.m.Chicago O'Hare Intl
1h 46m
3:36 p.m.Toronto Pearson Intl
Air Canada
26 Jun.
7:00 a.m.Toronto Pearson Intl
4h 41m
1 stop
11:41 a.m.Chicago O'Hare Intl
29 Jun.
2:20 p.m.Chicago O'Hare Intl
1h 39m
3:59 p.m.Toronto Pearson Intl
Air Canada
2 May
4:40 a.m.Toronto Pearson Intl
1h 44m
6:24 a.m.Chicago O'Hare Intl
29 May
9:30 a.m.Chicago O'Hare Intl
4h 52m
1 stop
2:22 p.m.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 Air Canada
Air Canada
8 Aug.
6:40 a.m.Toronto Pearson Intl
1h 50m
8:30 a.m.Chicago O'Hare Intl
Air Canada
8 May
10:45 a.m.Toronto Pearson Intl
1h 50m
12:35 p.m.Chicago O'Hare Intl
American Airlines
2 Jul.
7:38 a.m.Toronto Pearson Intl
1h 53m
9:31 a.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
Seattle to Chicago Flights
Fastest flight time
3h 55m
Cheapest price
198 C$
Buffalo to Chicago Flights
Fastest flight time
1h 52m
Cheapest price
262 C$
Toronto to Chicago Flights
Fastest flight time
1h 44m
Cheapest price
372 C$
Vancouver to Chicago Flights
Fastest flight time
3h 59m
Cheapest price
393 C$
Québec City to Chicago Flights
Fastest flight time
2h 45m
Cheapest price
430 C$
Ottawa to Chicago Flights
Fastest flight time
2h 18m
Cheapest price
430 C$
Calgary to Chicago Flights
Fastest flight time
5h 29m
Cheapest price
466 C$
Regina to Chicago Flights
Fastest flight time
9h 54m
Cheapest price
475 C$
Montreal to Chicago Flights
Fastest flight time
2h 26m
Cheapest price
506 C$
Victoria to Chicago Flights
Fastest flight time
8h 21m
Cheapest price
551 C$
Winnipeg to Chicago Flights
Fastest flight time
3h 56m
Cheapest price
552 C$
Sudbury to Chicago Flights
Fastest flight time
18h 20m
Cheapest price
593 C$
Grande Prairie to Chicago Flights
Fastest flight time
8h 31m
Cheapest price
616 C$
St. John's to Chicago Flights
Fastest flight time
14h 15m
Cheapest price
642 C$
Comox to Chicago Flights
Fastest flight time
12h 03m
Cheapest price
642 C$
Fort McMurray to Chicago Flights
Fastest flight time
9h 29m
Cheapest price
714 C$
London to Chicago Flights
Fastest flight time
7h 32m
Cheapest price
964 C$
Halifax to Chicago Flights
Fastest flight time
25h 17m
Cheapest price
1,143 C$
Saskatoon to Chicago Flights
Fastest flight time
25h 45m
Cheapest price
1,228 C$
Deer Lake to Chicago Flights
Fastest flight time
6h 21m
Cheapest price
1,260 C$
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