Cheap Flights to South Side: South Side Flight Deals

View €113 flight on Tue, 9 Jun 2026Opens in a new window

Flight 1

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Cheap round-trip flights to South Side

Prices were available within the past 7 days and start at €113 for one-way flights and €186 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Tue, 16 Jun - Fri, 19 Jun
YTZ
Toronto
ORD
Chicago
€186 Return, found 4 days ago
€186
Return
found 4 days ago
Select Air Canada flight, departing Tue, 16 Jun from Toronto to Chicago, returning Fri, 19 Jun, priced at €186 found 4 days ago
Porter Airlines
Thu, 28 May - Sun, 31 May
YTZ
Toronto
MDW
Chicago
€192 Return, found 4 days ago
€192
Return
found 4 days ago
Select Porter Airlines flight, departing Thu, 28 May from Toronto to Chicago, returning Sun, 31 May, priced at €192 found 4 days ago
Air Transat
Thu, 28 May - Sun, 31 May
YTZ
Toronto
MDW
Chicago
€213 Return, found 4 days ago
€213
Return
found 4 days ago
Select Air Transat flight, departing Thu, 28 May from Toronto to Chicago, returning Sun, 31 May, priced at €213 found 4 days ago
United
Tue, 16 Jun - Fri, 19 Jun
YTZ
Toronto
ORD
Chicago
€231 Return, found 4 days ago
€231
Return
found 4 days ago
Select United flight, departing Tue, 16 Jun from Toronto to Chicago, returning Fri, 19 Jun, priced at €231 found 4 days ago
Scandinavian Airlines
Mon, 11 Jan - Fri, 15 Jan
DUB
Dublin
ORD
Chicago
€473 Return, found 4 days ago
€473
Return
found 4 days ago
Select Scandinavian Airlines flight, departing Mon, 11 Jan from Dublin to Chicago, returning Fri, 15 Jan, priced at €473 found 4 days ago

Frequently asked questions

How do I find cheap flights to South Side that have flexible change policies?
When it comes to travelling 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 €186.
How much is a flight to South Side?
In the last seven days, return tickets to South Side sold from just €186 and reached a maximum price of €473. For one-way journeys departing from Toronto (YTZ), the lowest price during this time was only €113.
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.
How much is a plane ticket to South Side?
In the last seven days, tickets to South Side varied between €186 and €473. 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 holiday. Tickets are at a premium during the month of December, so keep clear of this time if you can.

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
€186

Trending flights to South Side

Prices were available within the past 7 days and start at €113 for one-way flights and €186 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Scandinavian Airlines
Mon, 11 Jan - Fri, 15 Jan
DUB
Dublin
ORD
Chicago
€473 Return, found 4 days ago
€473
Return
found 4 days ago
Select Scandinavian Airlines flight, departing Mon, 11 Jan from Dublin to Chicago, returning Fri, 15 Jan, priced at €473 found 4 days ago

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