Cheap Flights to Central Chicago , IL from CA $174

View CA $174 flight on Wed, Jul 29, 2026Opens in a new window

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How much is the cheapest flight to Central Chicago?

Prices were available within the past 7 days and start at CA $174 for one-way flights and CA $288 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Jul 2 - Wed, Jul 15
YTZ
Toronto
MDW
Chicago
CA $288 Roundtrip, just found
CA $288
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Jul 2 from Toronto to Chicago, returning Wed, Jul 15, priced at CA $288 just found
Air Canada
Thu, Jul 2 - Wed, Jul 15
YTZ
Toronto
ORD
Chicago
CA $288 Roundtrip, just found
CA $288
Roundtrip
just found
Select Air Canada flight, departing Thu, Jul 2 from Toronto to Chicago, returning Wed, Jul 15, priced at CA $288 just found
United
Mon, Jul 20 - Mon, Jul 27
YYZ
Toronto
ORD
Chicago
CA $300 Roundtrip, found 14 hours ago
CA $300
Roundtrip
found 14 hours ago
Select United flight, departing Mon, Jul 20 from Toronto to Chicago, returning Mon, Jul 27, priced at CA $300 found 14 hours ago
American Airlines
Wed, Jul 22 - Wed, Jul 29
YYZ
Toronto
ORD
Chicago
CA $300 Roundtrip, found 5 hours ago
CA $300
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Jul 22 from Toronto to Chicago, returning Wed, Jul 29, priced at CA $300 found 5 hours ago
Delta
Mon, Jul 20 - Mon, Jul 27
YYZ
Toronto
ORD
Chicago
CA $308 Roundtrip, found 14 hours ago
CA $308
Roundtrip
found 14 hours ago
Select Delta flight, departing Mon, Jul 20 from Toronto to Chicago, returning Mon, Jul 27, priced at CA $308 found 14 hours ago

Frequently asked questions

How do I find cheap flights to Central Chicago that have flexible change policies?
By using our smart "No change fee" filter, that's how. Just type in your dates and other details, click the "Search" button, then select the box directly below the "Flexible change policies" heading (it's on the left). Expedia makes it a cinch to find affordable, flexible tickets to Central Chicago.
Which airlines fly to Central Chicago?
Choose a seat with one of these airlines and dynamic Central Chicago will be yours to explore:

  • United Airlines - 12,777 flights to or near Central Chicago each month, including 12,777 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 9,109 flights to or near Central Chicago each month, including 9,109 flights to O'Hare Intl. Airport (ORD) per month.
  • Delta - 1,023 flights to or near Central Chicago each month, including 1,023 flights to O'Hare Intl. Airport (ORD) per month.

How can I find cheap tickets to Central Chicago?
Book well ahead, consider nearby airports, use frequent flyer miles — there are lots of ways! Another one is to take advantage of Expedia's "flexible dates" feature. Find your Central Chicago flight, then compare the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Central Chicago was CA $288.
How much is a flight to Central Chicago?
The cost of a round-trip flight to Central Chicago in the last seven days fluctuated between CA $288 and CA $308. If you were travelling one way from Toronto (YTZ), you could have nabbed a deal from only CA $174.
What are the most popular airports to fly into in Central Chicago?
Fly into O'Hare Intl. Airport (ORD) and sample all that Central Chicago has to offer. As the region's main entry point, roughly 24,728 flights land here every month.
When is the cheapest time to fly to Central Chicago?
If you'd rather spend your hard-earned vacation money on having fun in Central Chicago rather than on your trip there, take off early in the week. The cheapest day to fly is normally Tuesday, with Monday coming in second. With many people travelling on the weekend, Saturday tends to have the costliest fares.
How much is a plane ticket to Central Chicago?
Airfares ranged from CA $288 to CA $308 in the last seven days. When you're ready to book, we'll help you find a fabulous deal to Central Chicago.
What months are the cheapest to book a flight to Central Chicago?
To pick up a low-cost flight to Central Chicago, try to book during February when the price of airfares are at their lowest. When's the most expensive? In the U.S, it's the month of December.

Book with confidence

Expedia.ca gives you the best tools to secure great deals on flights to Central Chicago. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Central Chicago. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Central Chicago.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Central Chicago flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Central Chicago.

Looking to save even more? Get additional savings by bundling your Central Chicago flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Central Chicago trip!

Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $299

Trending flights to Central Chicago

Prices were available within the past 7 days and start at CA $174 for one-way flights and CA $288 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Jul 2 - Wed, Jul 15
YTZ
Toronto
MDW
Chicago
CA $288 Roundtrip, just found
CA $288
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Jul 2 from Toronto to Chicago, returning Wed, Jul 15, priced at CA $288 just found

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