Chicago (CHIA) Flights from C$137

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Flight deals to Chicago

Looking for a cheap last-minute deal or the best return flight to Chicago? If you want to travel to Chicago next month, return fares start from C$234. Find the lowest prices on one-way and return tickets right here.

Chicago.C$225 per passenger.Departing Wed., Jul. 15, returning Sat., Jul. 18.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed., Jul. 15, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sat., Jul. 18, arriving in Toronto Island.Price includes taxes and charges.From C$225, select.

Chicago.C$226 per passenger.Departing Tue., Jun. 30, returning Tue., Jul. 7.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue., Jun. 30, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Tue., Jul. 7, arriving in Toronto Island.Price includes taxes and charges.From C$226, select.

Chicago.C$228 per passenger.Departing Mon., May 11, returning Wed., Aug. 19.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon., May 11, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Wed., Aug. 19, arriving in Toronto Island.Price includes taxes and charges.From C$228, select.

Chicago.C$229 per passenger.Departing Fri., Jul. 31, returning Wed., Aug. 5.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Fri., Jul. 31, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Wed., Aug. 5, arriving in Toronto Island.Price includes taxes and charges.From C$229, select.

Chicago.C$230 per passenger.Departing Tue., Apr. 28, returning Thu., May 7.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue., Apr. 28, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Thu., May 7, arriving in Toronto Island.Price includes taxes and charges.From C$230, select.

Chicago.C$231 per passenger.Departing Wed., Aug. 19, returning Sat., Aug. 29.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed., Aug. 19, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sat., Aug. 29, arriving in Toronto Island.Price includes taxes and charges.From C$231, select.

Chicago.C$233 per passenger.Departing Thu., Jun. 4, returning Sun., Jun. 7.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Thu., Jun. 4, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sun., Jun. 7, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$233, select.

Chicago.C$233 per passenger.Departing Fri., May 29, returning Tue., Jun. 2.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Fri., May 29, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Tue., Jun. 2, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$233, select.

Chicago.C$234 per passenger.Departing Fri., May 22, returning Tue., May 26.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Fri., May 22, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Tue., May 26, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$234, select.

Chicago.C$240 per passenger.Departing Sun., Apr. 19, returning Thu., Apr. 23.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sun., Apr. 19, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Thu., Apr. 23, arriving in Toronto Island.Price includes taxes and charges.From C$240, select.

Chicago.C$243 per passenger.Departing Mon., May 18, returning Wed., May 20.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon., May 18, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Wed., May 20, arriving in Toronto Island.Price includes taxes and charges.From C$243, select.

Chicago.C$244 per passenger.Departing Wed., Jun. 17, returning Tue., Jun. 23.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed., Jun. 17, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Tue., Jun. 23, arriving in Toronto Island.Price includes taxes and charges.From C$244, select.

Chicago.C$245 per passenger.Departing Sat., Aug. 29, returning Thu., Sep. 3.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat., Aug. 29, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago O'Hare International on Thu., Sep. 3, arriving in Toronto Island.Price includes taxes and charges.From C$245, select.

Chicago.C$246 per passenger.Departing Sun., May 31, returning Tue., Jun. 2.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sun., May 31, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Tue., Jun. 2, arriving in Toronto Island.Price includes taxes and charges.From C$246, select.

Chicago.C$250 per passenger.Departing Thu., Sep. 3, returning Tue., Sep. 8.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu., Sep. 3, arriving in Chicago O'Hare International.Inbound direct flight with Porter Airlines departs from Chicago O'Hare International on Tue., Sep. 8, arriving in Toronto Island.Price includes taxes and charges.From C$250, select.

Chicago.C$259 per passenger.Departing Sat., Oct. 17, returning Mon., Oct. 19.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat., Oct. 17, arriving in Chicago O'Hare International.Inbound direct flight with Porter Airlines departs from Chicago O'Hare International on Mon., Oct. 19, arriving in Toronto Island.Price includes taxes and charges.From C$259, select.

Find the cheapest time to fly to Chicago

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

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Cheapest month:July

Most expensive month:March

Airports in Chicago

Compare routes to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier.

Direct flights to Chicago

Frequently asked questions

How long is the flight to Chicago?

The average flight time to Chicago is 2 hours and 26 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, Air Canada, Republic Airways, Qatar Airways, American Airlines, Air New Zealand, SkyWest Airlines and British Airways all fly direct to Chicago.

When is the cheapest time to fly to Chicago?

The cheapest month to fly to Chicago is usually July.

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 59 minutes.

How much are return flights to Chicago?

The best price we found for a return flight to Chicago is C$225. 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.

Which is the cheapest airport in Chicago?

The cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from C$225.

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 Wednesday, July 15, 2026.

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 April is around 8°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 to Chicago with?

Currently, Porter Airlines offers the cheapest flight tickets to Chicago.

Flying to Chicago

The things to know before you go.

Cheapest flight found	C$137
Cheapest month to fly	July
Average flight time	2 hrs, 59 mins
Most popular airline	United
Average flights per week	1,343

Discover Chicago

How to find cheap flights to Chicago in 2026

Looking for cheap tickets to Chicago? Round-trip tickets to Chicago start from C$225 and one-way flights to Chicago start from C$137.

Here are a few tips on how to score the best price and make your journey as smooth as possible.

Simply hit "search." We've compared plane tickets from all major online travel agents and airlines flying to Chicago to find the cheapest flights. And with us, there are no hidden fees – what you see is what you pay.
Depart from the cheapest location. Look out for flights from Canada - this is the cheapest location to depart from when flying to Chicago.
Fly to the cheapest airport. Search for flights to Chicago Midway Airport - this is the cheapest airport to fly to when travelling to Chicago.
Set up a Price Alert. You can easily track the fare of your flights to Chicago by creating an alert. Whenever prices go up or down, you'll get a push notification or email to help you get the best flight deal.
Flex your dates to secure the best air ticket price for your Chicago flight. If your travel dates are flexible, use Skyscanner's "Whole month" tool to find the cheapest time to fly to Chicago.
Compare flight deals to Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from C$137 one-way.
Include nearby airports in your search. Widen your search for Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel. For reference, Chicago Midway
Chicago O'Hare International
Chicago Dupage County
Chicago Rockford serve Chicago.
Look for direct flights. Only interested in direct flights to Chicago? Make sure to check "Direct flights only" when performing a search. Airlines that fly direct to Chicago: United
Air Canada
Republic Airways
Qatar Airways
American Airlines
Air New Zealand
SkyWest Airlines
British Airways
Find the cheapest Business class flights to Chicago. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare.
Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets to Chicago whenever you want.
Flexible on when you travel? The cheapest month to fly to Chicago is July.

Combine your flight to Chicago with hotels and car rental

Once you've secured your cheap flight ticket to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car rental companies all at once so you get the best car rental price for your trip.

Compare Chicago plane tickets with other destinations using the everywhere search

Not quite set on flying to Chicago just yet? You can easily browse other destinations by searching flights to "Everywhere" – this will allow you to find the cheapest place to travel.