Cheap Flights to West Side , IL from CA $185

View CA $185 flight on Fri, May 29, 2026Opens in a new window

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How much is the cheapest flight to West Side?

Prices were available within the past 7 days and start at CA $185 for one-way flights and CA $309 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, May 29 - Sun, May 31
YTZ
Toronto
MDW
Chicago
CA $309 Roundtrip, just found
CA $309
Roundtrip
just found
Select Porter Airlines flight, departing Fri, May 29 from Toronto to Chicago, returning Sun, May 31, priced at CA $309 just found
Air Canada
Tue, Apr 21 - Sat, Apr 25
YTZ
Toronto
ORD
Chicago
CA $330 Roundtrip, found 5 days ago
CA $330
Roundtrip
found 5 days ago
Select Air Canada flight, departing Tue, Apr 21 from Toronto to Chicago, returning Sat, Apr 25, priced at CA $330 found 5 days ago
Air Transat
Fri, May 29 - Sun, May 31
YTZ
Toronto
MDW
Chicago
CA $351 Roundtrip, just found
CA $351
Roundtrip
just found
Select Air Transat flight, departing Fri, May 29 from Toronto to Chicago, returning Sun, May 31, priced at CA $351 just found
United
Wed, Jun 10 - Thu, Jun 11
YYZ
Toronto
ORD
Chicago
CA $364 Roundtrip, found 1 hour ago
CA $364
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Jun 10 from Toronto to Chicago, returning Thu, Jun 11, priced at CA $364 found 1 hour ago
American Airlines
Thu, Jun 4 - Wed, Jun 10
YYZ
Toronto
ORD
Chicago
CA $364 Roundtrip, just found
CA $364
Roundtrip
just found
Select American Airlines flight, departing Thu, Jun 4 from Toronto to Chicago, returning Wed, Jun 10, priced at CA $364 just found

Frequently asked questions

How do I find cheap flights to West Side that have flexible change policies?
By using our nifty "No change fee" filter, that's how. Simply enter your travel dates, click the "Search" button, then tick the checkbox directly under the "Flexible change policies" subheading (look to the left of your screen). Expedia makes it a cinch to find cheap, flexible fares to West Side.
Which airlines fly to West Side?
Work out your perfect travel dates and then take off towards West Side with one of these quality airlines:

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

How can I find cheap tickets to West Side?
One of the easiest ways to find cheap tickets to West Side is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. You'll see the cheapest prices for nearby days. The best price for a flight to West Side in the last seven days was CA $309. Booking well ahead of time will generally help you pick up an even bigger bargain.
How much is a flight to West Side?
In the last seven days, round-trip flights to West Side sold for as low as CA $309 and peaked at CA $364. For one-way fares taking off from Toronto (YTZ), the lowest amount paid during this same period was just CA $185.
What are the most popular airports to fly into in West Side?
Jet into O'Hare Intl. Airport (ORD) and experience everything that West Side has to offer. As the region's primary entry point, around 24,728 flights touch down here every month.
When is the cheapest time to fly to West Side?
Jetting off on a Tuesday, followed by a Monday, is generally the best way to score the cheapest deal. Steer clear of weekends if possible, because Saturday is typically the most expensive day. Spend the money you saved having a blast in West Side instead!
How much is a plane ticket to West Side?
In the last seven days, airfares to West Side fluctuated from CA $309 to CA $364.
What months are the cheapest to book a flight to West Side?
February is the best month to book your West Side trip. Fares are at a premium during the festive month of December, so avoid this time if you can.

Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $309

Trending flights to West Side

Prices were available within the past 7 days and start at CA $185 for one-way flights and CA $309 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, May 29 - Sun, May 31
YTZ
Toronto
MDW
Chicago
CA $309 Roundtrip, just found
CA $309
Roundtrip
just found
Select Porter Airlines flight, departing Fri, May 29 from Toronto to Chicago, returning Sun, May 31, priced at CA $309 just found

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