Cheap Flights to Southwest Side , IL from CA $152

View CA $152 flight on Sat, Oct. 25, 2025Opens in a new window

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How much is the cheapest flight to Southwest Side?

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Nov. 6 - Sun, Nov. 9
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 4 hours ago
CA $244
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Thu, Nov. 6 from Toronto to Chicago, returning Sun, Nov. 9, priced at CA $244 found 4 hours ago
United
Sat, Nov. 8 - Sat, Nov. 15
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 1 hour ago
CA $244
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Nov. 8 from Toronto to Chicago, returning Sat, Nov. 15, priced at CA $244 found 1 hour ago
WestJet
Sat, Oct. 11 - Mon, Oct. 27
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 1 day ago
CA $256
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Oct. 11 from Calgary to Chicago, returning Mon, Oct. 27, priced at CA $256 found 1 day ago
American Airlines
Fri, Oct. 24 - Mon, Oct. 27
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 1 day ago
CA $256
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct. 24 from Calgary to Chicago, returning Mon, Oct. 27, priced at CA $256 found 1 day ago
Porter Airlines
Tue, Jul. 22 - Mon, Aug. 11
YTZ
Toronto
MDW
Chicago
CA $256 Roundtrip, found 1 day ago
CA $256
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Tue, Jul. 22 from Toronto to Chicago, returning Mon, Aug. 11, priced at CA $256 found 1 day ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (MDW)

August is typically the cheapest month to fly

From CA $149 - CA $752 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Southwest Side. 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 Southwest Side. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Southwest Side.

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 Southwest Side 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 Southwest Side.

Looking to save even more? Get additional savings by bundling your Southwest Side 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 Southwest Side trip!

Frequently asked questions

How do I find cheap flights to Southwest Side that have flexible change policies?
By using our handy "No change fee" filter, that's how. Just type in your preferred dates and destination, click "Search," then mark the checkbox directly below the "Flexible change policies" heading (it's on the top left of your screen). Expedia makes it a snap to find low-cost, flexible fares to Southwest Side.
Which airlines fly to Southwest Side?
You can take your pick of a variety of airlines that operate services in or near Southwest Side. A few of your options are:

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

How can I find cheap tickets to Southwest Side?
One of the easiest ways to get a hold of cheap tickets to Southwest Side is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It'll bring up the cheapest prices for nearby days. The best price for a flight to Southwest Side in the last seven days was CA $244. Booking ahead of time will usually help you get an even better deal.
How much is a flight to Southwest Side?
You could have picked up a return airfare to Southwest Side from anywhere between CA $244 and CA $256 in the last seven days. For one-way trips leaving from Toronto (YTZ), the lowest amount paid during this period was CA $152.
What are the most popular airports to fly into in Southwest Side?
O'Hare Intl. Airport (ORD) is the primary gateway for people hoping to explore Southwest Side. Roughly 24,728 flights per month land at this airport.
When is the cheapest time to fly to Southwest Side?
If you're not fixed on your travel dates to Southwest Side, fly out earlier in the week. The most economical day to take off is usually Tuesday, followed closely by Monday. Saturday is typically the costliest day, with many vacationers opting to fly on the weekend.
How much is a plane ticket to Southwest Side?
In the last seven days, plane tickets to Southwest Side ranged between CA $244 and CA $256. Prices tend to rise over time, so find an awesome deal today.
What is the best time to go to Southwest Side?
Just about anytime is a good time to head to Southwest Side, with awesome places like Drexel Estate to discover for yourself. If you don't mind a crowd, May, June and August are the most popular months for newcomers. Summertime starts June 20 here. If you're visiting around this time, take some sunscreen and a wide-brimmed hat. Summer temperatures range between 18ºC and 26ºC in Drexel Estate.
What months are the cheapest to book a flight to Southwest Side?
Score a ticket in February to unlock the lowest-priced flights to Southwest Side. The month of December is known to be the most expensive time to buy a fare.
Flights to Southwest Side information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $244

Trending flights to Southwest Side

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Nov. 6 - Sun, Nov. 9
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 4 hours ago
CA $244
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Thu, Nov. 6 from Toronto to Chicago, returning Sun, Nov. 9, priced at CA $244 found 4 hours ago
*Available to Expedia members.