Cheap Flights to South Side , IL from CA $143

View CA $143 flight on Wed, Aug. 27, 2025Opens in a new window

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How much is the cheapest flight to South Side?

Prices were available within the past 7 days and start at CA $143 for one-way flights and CA $226 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Wed, Aug. 27 - Sun, Aug. 31
YTZ
Toronto
MDW
Chicago
CA $226 Roundtrip, just found
CA $226
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Aug. 27 from Toronto to Chicago, returning Sun, Aug. 31, priced at CA $226 just found
Air Canada
Sat, Aug. 30 - Sat, Sep. 6
YTZ
Toronto
ORD
Chicago
CA $226 Roundtrip, found 1 hour ago
CA $226
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sat, Aug. 30 from Toronto to Chicago, returning Sat, Sep. 6, priced at CA $226 found 1 hour ago
United
Sat, Sep. 27 - Sun, Sep. 28
YYZ
Toronto
ORD
Chicago
CA $235 Roundtrip, just found
CA $235
Roundtrip
just found
Select United flight, departing Sat, Sep. 27 from Toronto to Chicago, returning Sun, Sep. 28, priced at CA $235 just found
WestJet
Thu, Oct. 16 - Thu, Oct. 23
YYC
Calgary
ORD
Chicago
CA $249 Roundtrip, found 5 hours ago
CA $249
Roundtrip
found 5 hours ago
Select WestJet flight, departing Thu, Oct. 16 from Calgary to Chicago, returning Thu, Oct. 23, priced at CA $249 found 5 hours ago
American Airlines
Fri, Oct. 24 - Fri, Nov. 7
YYZ
Toronto
ORD
Chicago
CA $260 Roundtrip, just found
CA $260
Roundtrip
just found
Select American Airlines flight, departing Fri, Oct. 24 from Toronto to Chicago, returning Fri, Nov. 7, priced at CA $260 just found

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

August is typically the cheapest month to fly

From CA $147 - CA $754 per traveller.

Graph displaying average flight prices per month

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

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

Frequently asked questions

How do I find cheap flights to South Side that have flexible change policies?
It's as easy as can be with Expedia. Firstly, type in your travel details and click on the "Search" button. Next step? Check "No change fee" just under the "Flexible change policies" subheading on the left-hand side of your screen. Step 3. Score a cheap and flexible flight to South Side.
Which airlines fly to South Side?
Dust off your suitcase and choose from these popular airlines that fly into or near South Side:

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

How can I find cheap tickets to South Side?
Start searching as early as possible, fly to or from nearby airports, use miles or points — there's no shortage of ways! One more is to make the most of Expedia's "flexible dates" function. Find your South Side flight, then check out the prices for nearby dates. In the last seven days, the best price for a flight to South Side was CA $226.
How much is a flight to South Side?
In the last seven days, round-trip tickets to South Side sold for as little as CA $226 and reached a maximum of CA $260. For one-way trips departing from Toronto (YTZ), the lowest price during this time was just CA $143.
What are the most popular airports to fly into in South Side?
Jet into O'Hare Intl. Airport (ORD) and sample everything that South Side has to offer. As the region's primary entry point, approximately 24,728 flights touch down here each month.
When is the cheapest time to fly to South Side?
Consider leaving early on in the week to bag the best airfare to South Side. Tuesday is normally the most economical day to depart, with Monday right behind it. Saturday typically has the costliest prices. This is because many travellers prefer to start their break on a weekend.
How much is a plane ticket to South Side?
In the last seven days, airfares to South Side ranged between CA $226 and CA $260. Prices generally depend on the departure time, airline, seating class and when you make your booking.
What months are the cheapest to book a flight to South Side?
February is a great month to secure an impressive deal to South Side. Bear in mind that the priciest time to book a seat in the USA isn't during the peak of summer, but the month of December.
Flights to South Side information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $225

Trending flights to South Side

Prices were available within the past 7 days and start at CA $143 for one-way flights and CA $226 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Wed, Aug. 27 - Sun, Aug. 31
YTZ
Toronto
MDW
Chicago
CA $226 Roundtrip, just found
CA $226
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Aug. 27 from Toronto to Chicago, returning Sun, Aug. 31, priced at CA $226 just found
*Available to Expedia members.