Cheap Flights to South Side

View ₩145,300 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 ₩145,300 for one-way flights and ₩228,900 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
₩228,900 Roundtrip, found 20 hours ago
₩228,900
Roundtrip
found 20 hours ago
Select Porter Airlines flight, departing Wed, Aug 27 from Toronto to Chicago, returning Sun, Aug 31, priced at ₩228,900 found 20 hours ago
Air Canada
Mon, Sep 22 - Tue, Sep 30
YYZ
Toronto
ORD
Chicago
₩236,700 Roundtrip, found 4 hours ago
₩236,700
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Mon, Sep 22 from Toronto to Chicago, returning Tue, Sep 30, priced at ₩236,700 found 4 hours ago
United
Mon, Sep 1 - Thu, Sep 4
YYZ
Toronto
ORD
Chicago
₩238,300 Roundtrip, found 17 hours ago
₩238,300
Roundtrip
found 17 hours ago
Select United flight, departing Mon, Sep 1 from Toronto to Chicago, returning Thu, Sep 4, priced at ₩238,300 found 17 hours ago
American Airlines
Sat, Nov 1 - Sat, Nov 15
YYZ
Toronto
ORD
Chicago
₩263,800 Roundtrip, found 1 day ago
₩263,800
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Nov 1 from Toronto to Chicago, returning Sat, Nov 15, priced at ₩263,800 found 1 day ago
Delta
Sat, Nov 1 - Sat, Nov 15
YYZ
Toronto
MDW
Chicago
₩295,000 Roundtrip, found 1 day ago
₩295,000
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 1 from Toronto to Chicago, returning Sat, Nov 15, priced at ₩295,000 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 ₩148,416 - ₩763,042 per traveler.

Graph displaying average flight prices per month

Searching for cheap flights to South Side? No travel company presents more choices than Expedia if you're looking to compare flights to South Side. With more airlines, cheaper flights, fewer stops, and more departure and arrival times travellers should ensure they search on Expedia before any holiday to Chicago. Expedia provides the cheapest flights to many destinations in Chicago and you may find even greater savings if you combine your flight with a hotel stay in South Side.

Frequently asked questions

How do I find cheap flights to South Side that have flexible change policies?
When it comes to traveling these days, flexibility is crucial. That's why we have a "No change fee" search function to help you track down flexible, affordable tickets to South Side. It's near the top left of your screen directly underneath the "Flexible change policies" subheading.
Which airlines fly to South Side?
When you're ready to book your ticket to or near South Side, these well-known airlines look forward to welcoming you aboard:

  • United Airlines - 12,950 flights to or near South Side each month, including 12,950 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 8,855 flights to or near South Side each month, including 8,855 flights to O'Hare Intl. Airport (ORD) per month.
  • Delta Air Lines - 1,222 flights to or near South Side each month, including 1,222 flights to O'Hare Intl. Airport (ORD) per month.

How can I find cheap tickets to South Side?
Book well ahead of time, consider nearby airports, avoid peak travel periods — you're not short of ways! One more is to use Expedia's "flexible dates" function. Find a South Side flight, then compare the prices for nearby dates. In the last seven days, the lowest price for a flight to South Side was ₩228,900.
How much is a flight to South Side?
In the last seven days, return tickets to South Side sold from just ₩228,900 and reached a maximum price of ₩757,000. For one-way journeys departing from Toronto (YTZ), the lowest price during this time was only ₩145,300.
What are the most popular airports to fly into in South Side?
Get set to pack your bags and fly into O'Hare Intl. Airport (ORD), South Side's major flight hub. Lock in a seat on one of the 25,318 flights that touch down at this top destination every month.
When is the cheapest time to fly to South Side?
Jet off on a Tuesday to increase your chances of picking up the cheapest deal to South Side. Mondays are usually the second most affordable day to depart. Saturday is typically the costliest day to fly anywhere.
How much is a plane ticket to South Side?
In the last seven days, tickets to South Side varied between ₩228,900 and ₩757,000. Prices generally depend on the departure time, cabin class, airline and how early the fare is booked.
What months are the cheapest to book a flight to South Side?
February is the most affordable month to book your South Side vacation. Tickets are at a premium during the month of December, so keep clear of this time if you can.
Flights to South Side information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
₩228,900

Trending flights to South Side

Prices were available within the past 7 days and start at ₩145,300 for one-way flights and ₩228,900 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, Oct 17 - Tue, Oct 21
ICN
Seoul
ORD
Chicago
₩757,000 Roundtrip, found 4 hours ago
₩757,000
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Fri, Oct 17 from Seoul to Chicago, returning Tue, Oct 21, priced at ₩757,000 found 4 hours ago
*Available to Expedia members.