Cheap Flights to South Side , IL from CA $187

View CA $187 flight on Mon, Jul 27, 2026Opens 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 $187 for one-way flights and CA $300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Mon, Jul 27 - Fri, Jul 31
YKF
Kitchener
ORD
Chicago
CA $300 Roundtrip, found 7 hours ago
CA $300
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Mon, Jul 27 from Kitchener to Chicago, returning Fri, Jul 31, priced at CA $300 found 7 hours ago
American Airlines
Wed, May 6 - Sat, May 9
YYZ
Toronto
ORD
Chicago
CA $301 Roundtrip, just found
CA $301
Roundtrip
just found
Select American Airlines flight, departing Wed, May 6 from Toronto to Chicago, returning Sat, May 9, priced at CA $301 just found
Delta
Mon, Jun 1 - Sat, Jun 6
YYZ
Toronto
ORD
Chicago
CA $308 Roundtrip, just found
CA $308
Roundtrip
just found
Select Delta flight, departing Mon, Jun 1 from Toronto to Chicago, returning Sat, Jun 6, priced at CA $308 just found
Porter Airlines
Fri, May 29 - Fri, Jun 5
YUL
Montreal
MDW
Chicago
CA $313 Roundtrip, found 6 days ago
CA $313
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Fri, May 29 from Montreal to Chicago, returning Fri, Jun 5, priced at CA $313 found 6 days ago
United
Tue, Jun 30 - Tue, Jul 14
YYZ
Toronto
ORD
Chicago
CA $319 Roundtrip, found 7 hours ago
CA $319
Roundtrip
found 7 hours ago
Select United flight, departing Tue, Jun 30 from Toronto to Chicago, returning Tue, Jul 14, priced at CA $319 found 7 hours ago

Alternative airports

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Flights from CA $480
ORD
O'Hare Intl.
Cheapest
Flights from CA $480

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 $300.
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 $300 and reached a maximum of CA $319. For one-way trips departing from Hamilton (YHM), the lowest price during this time was just CA $187.
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 $300 and CA $319. 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.

Book with confidence

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!

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $300

Trending flights to South Side

Prices were available within the past 7 days and start at CA $187 for one-way flights and CA $300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Mon, Jul 27 - Fri, Jul 31
YKF
Kitchener
ORD
Chicago
CA $300 Roundtrip, found 7 hours ago
CA $300
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Mon, Jul 27 from Kitchener to Chicago, returning Fri, Jul 31, priced at CA $300 found 7 hours ago

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