How long is the flight to Chicago?

The average flight time to Chicago is 2 hours and 20 minutes. We've calculated this based on journeys from Ottawa.

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

Which airlines offer direct flights to Chicago?

United, American Airlines, Air Canada, Alaska Airlines, Envoy Air, Air New Zealand, Qatar Airways and Republic Airways all fly non-stop to Chicago.

When is the cheapest time to fly to Chicago?

The cheapest month to fly to Chicago is usually May.

How can I find the best flight deal to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

Can I get a direct flight to Chicago?

Yes – you can fly direct to Chicago Midway Airport or Chicago O'Hare International Airport, and the average flight time is 2 hours and 46 minutes.

How much are round-trip flights to Chicago?

The best price we found for a round-trip flight to Chicago is C$265. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

What's the cheapest airport in Chicago?

The cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from C$265 .

Which upcoming date is cheapest to fly to Chicago on?

After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago is Friday, May 31, 2024 .

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

The average temperature in Chicago in May is around 13°C. The warmest month in Chicago is typically July, which averages 26°C. The coolest month is January, with temperatures averaging -8°C. The rainiest month is August, and it usually rains the least in January.

Which is the cheapest airline to fly with to Chicago?

Currently, WestJet offers the cheapest flight tickets to Chicago.

Cheap flights to Chicago from C$155

Compare Chicago flights across hundreds of providers

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals to Chicago

Looking for a cheap last-minute deal or the best round-trip flight to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

Chicago.C$155 per passenger.Departing Mon, May 13.One-way flight with Flair Airlines.Outbound indirect flight with Flair Airlines, departing from Toronto Pearson International on Mon, May 13, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$155, select.

Chicago.C$158 per passenger.Departing Sat, Jun 1.One-way flight with WestJet.Outbound direct flight with WestJet departing from Calgary on Sat, Jun 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$158, select.

Chicago.C$160 per passenger.Departing Thu, May 23.One-way flight with WestJet.Outbound direct flight with WestJet departing from Calgary on Thu, May 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$160, select.

Chicago.C$176 per passenger.Departing Fri, Sep 13.One-way flight with WestJet.Outbound direct flight with WestJet departing from Calgary on Fri, Sep 13, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$176, select.

Chicago.C$178 per passenger.Departing Mon, Aug 5.One-way flight with WestJet.Outbound direct flight with WestJet departing from Calgary on Mon, Aug 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$178, select.

Chicago.C$204 per passenger.Departing Thu, Jul 4.One-way flight with WestJet.Outbound direct flight with WestJet departing from Calgary on Thu, Jul 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$204, select.

Chicago.C$215 per passenger.Departing Thu, Oct 3.One-way flight with WestJet.Outbound direct flight with WestJet departing from Calgary on Thu, Oct 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$215, select.

Chicago.C$284 per passenger.Departing Fri, Nov 22.One-way flight with Delta.Outbound indirect flight with Delta, departing from Calgary on Fri, Nov 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$284, select.

Find the cheapest time to fly to Chicago

Flexible on travel dates? Find the cheapest month – or even day – to fly to Chicago.

May

Jun

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Oct

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Dec

Jan

Feb

Mar

Apr

Airports in Chicago

Looking for the best route? There are 4 airports in and around Chicago.

Direct flights to Chicago

Alaska Airlines

Frequently asked questions

: The average flight time to Chicago is 2 hours and 20 minutes. We've calculated this based on journeys from Ottawa.
: There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
: United, American Airlines, Air Canada, Alaska Airlines, Envoy Air, Air New Zealand, Qatar Airways and Republic Airways all fly non-stop to Chicago.
: The cheapest month to fly to Chicago is usually May.
: We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
: Yes – you can fly direct to Chicago Midway Airport or Chicago O'Hare International Airport, and the average flight time is 2 hours and 46 minutes.
: The best price we found for a round-trip flight to Chicago is C$265. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
: The cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from C$265.
: After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago is Friday, May 31, 2024.
: We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
: The average temperature in Chicago in May is around 13°C. The warmest month in Chicago is typically July, which averages 26°C. The coolest month is January, with temperatures averaging -8°C. The rainiest month is August, and it usually rains the least in January.
: Currently, WestJet offers the cheapest flight tickets to Chicago.

Flying to Chicago

The things to know before you go.

Cheapest flight found	C$155
Cheapest month to fly	May
Average flight time	2 hrs, 46 mins
Most popular airline	United
Average flights per week	1,121

Discover Chicago

Flights to Chicago

As one of the top visited cities in the United States, Chicago boasts a vibrant art, culture and entertainment scene, as well as a thriving nightlife. Its praised for its grand and equally innovative architecture which you can see across the city – and most predominantly along the Riverwalk. The third-largest city in America, this bustling metropolis is sure to have something to please every Canadian traveler.

Chicago Travel Guide

Cheap Flights to Chicago

Thinking of taking a vacation to Chicago? From Canada, you can easily book cheap flights to Chicago, flying into either Chicago O'Hare International Airport , or Chicago Midway Airport. Airlines that fly to Chicago O’Hare International Airport from Canada include: Air Canada, American Airlines, and United Airlines. While Porterflights to Chicago arrive at Chicago Midway Airport.

Direct Flights to Chicago from Canada
Flight Route	Departing Airport	Flight Time	Best Return Flight Price
Flights to Chicago from Toronto	Toronto Pearson International Airport (YYZ) and Billy Bishop Toronto City Airport (YTZ)	1h 40min	C$ 212
Flights to Chicago from Vancouver	Vancouver International Airport (YYC)	3h 52min	C$ 325
Flights to Chicago from Calgary	Calgary International Airport (YYC)	3h 19min	C$ 274
Flights to Chicago from Montreal	Montreal Pierre Elliott Trudeau Airport (YUL)	2h 23min	C$ 246

Toronto to Chicago Flights

There are approximately 172 flights from Toronto to Chicago every week. Cheap flights from Toronto to Chicago are available year-round, from both Toronto Pearson International Airport (YYZ) and Billy Bishop Toronto City Airport (YTZ), arriving at either Chicago O'Hare International Airport, or Chicago Midway Airport. Flights to Chicago cost roughly C$ 126 for a one-way fare.

Vancouver to Chicago Flights

Flights from Vancouver to Chicago are popular among both business and leisure travelers. Cheap flights to Chicago from Vancouver are in demand across the whole year. Travelers can expect to pay around C$ 185 for one-way Vancouver to Chicago flights.

Arriving in Chicago

There are two major airports in Chicago, Illinois: Chicago O'Hare International Airport and Chicago Midway Airport.

Arriving at Chicago is O’Hare International Airport

The largest airport in Chicago is O’Hare International Airport in the city’s northwest region and is a major hub for international flights. For those on a budget, the CTA Blue Line station is located within the airport and offers easy access to downtown Chicago and beyond. A number of airport shuttles and regional buses service O'Hare International Airport (ORD), offering passengers transportation to the city, suburbs and surrounding states.

Arriving at Chicago Midway International Airport

Chicago Midway International Airport is the smaller Chicago’s two airports and is located in southwest Chicago. From Midway International Airport (MDW), you can easily get to the city centre using public transportation. Looking for a more comfortable ride to your accommodation dwellings? A taxi will set you back around US$ 60 to get to downtown Chicago while rideshare cars are slightly cheaper at approximately US $45. Either airport is a great choice for Canadians to fly into when looking for cheap flights to Chicago.

Chicago Travel Information

Traveling to Chicago? Here’s what you need to know to make your journey as smooth as possible.

Essential Chicago Travel Information
Getting Around Chicago	Chicago offers the third-largest transportation system in the United States. Tourists will find it relatively easy to navigate the Chicago cityscape with its vast network of public buses and elevated trains, for which fares start at USD $1.
Car Hire, Chicago	Enhance your vacation by exploring even more of Chicago. Cheap car rental services are available at both Chicago airports.
Weather in Chicago	As Chicago’s nickname suggests, the 'Windy City' can be a frosty adventure in the winter with temperatures as low as 10°C, combined with arctic winds. In summer, the temperature rises to an average of 29°C.
Best Time to Visit Chicago	The best time to visit Chicago is in the summer when the beaches and parks come alive with outdoor events. The fall is also a great time to visit as the sun continues to shine, but the city sees fewers tourists and lower hotel prices.

Flights to Chicago: Frequently Asked Questions

When is it best to book flights to Chicago?

Historical data shows that November is the cheapest month to book flights to Chicago from Canada. Flights during this period are 5% cheaper on average than in other months. However, prices will vary depending on departure airport and other factors (such as the day or time that you book, and how far in advance you are searching for flight tickets) can influence flight prices too.

How to find cheap flights to Chicago?

Our data also shows that April is also the cheapest month to fly to Chicago from Canada. Chicago flights bought for travel in April are on average 5% cheaper than flights bought in other months. Make sure you’re getting the best Chicago flights by signing up to Skyscanner Price Alerts.

What time zone is Chicago on?

Chicago is on Central Time, so you’ll need to adjust your watch accordingly.

What to do in Chicago?

Travelers from Canada and the rest of the globe flock to Chicago for its arts, culture and music scenes. Among the most popular things to do in Chicago is to tour the city’s many museums and galleries, including the renowned Art Institute of Chicago, and the Shedd Aquarium. Chicago is frequently named one of the best US cities for sports, so be sure to check out the iconic baseball stadium, Wrigley Field.

What to see in Chicago?

A must-do while you’re in Chicago is to take photo with the mirrored Cloud Gate sculpture in Millennium Park. More impressive Chicago attractions await to be seen from the soaring heights of the 110 storey-tall Willis Tower. However, if you’d rather marvel at the city’s edifices and skyscrapers from the ground, the 90-minute Architecture River Tour will inform you of everything you need to know about the city’s illustrious past and present.

Where to eat in Chicago?

Whether you’re a fan of fine dining, deep-fried grub or a href="https://www.skyscanner.ca/trip/get-crafty-chicagos-microbrew-scene-liz-behler"craft beer, Chicago is a great destination to take your tastebuds on an adventure. The Girl and Goat is one of the most-talked about restaurants in the city, receiving rave reviews for both its innovative menu and interior design. Another popular pick is the The Purple Pig which is known for its swine and wine-themed menu. However, you can’t leave Chicago without taking a cheesy bite of the city’s famous deep-dish pizza.

Where to shop in Chicago?

On the hunt to pick up some fashion-forward buys? Head straight to Chicago’s main shopping strip The Magnificent Mile where you can browse everything from luxury goods to high-street fashion.

Where to stay in Chicago?

Chicago has of great places to stay, with 3* hotels on offer from US$ 69/night. Top-rated hotels include the Double Tree by Hilton Chicago Magnificent Mile, and Claridge House. 5* hotels include The Peninsula Chicago and Waldorf Astoria Chicago which can be found from US$ 312/night.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.

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