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 .

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.

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$. If you don’t want to visit Chicago in April, then you should wait until March to fly from Canada, when ticket prices are also cheap, with an average price of 285 C$.

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.

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 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.

Find Cheap Flights to Chicago from 188 C$

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$

CHEAPEST MONTH TO FLY TO CHICAGO FROM SEATTLE	August	35% cheaper	Flying from Seattle to Chicago costs on average just 173 C$ in August
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM SEATTLE	December	39% more expensive	It costs about 373 C$ for flights to Chicago from Seattle in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM SEATTLE	October	271% more users visited	More momondo users searched in flights to Chicago from Seattle in October than any other month

Find cheap flights to Chicago

Cheapest flights to Chicago airports

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

When is the best time to fly to Chicago?

What is the absolute cheapest flight to Chicago?

What is the cheapest month to fly to Chicago?

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

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

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

Is there a good place to hike near Chicago?

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

Is there an alternative airport near Chicago?

Is there a cheaper alternative to flying into Chicago?

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 to Chicago, view some of our deals below provided by Air Canada

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

Start planning your trip to Chicago

Start planning your trip today

Top car rentals in Chicago

Stay at a vacation rental

Flights to other cities in United States

Lost the lust for Chicago? Check out some flights to other cities in United States