Cheap Flights to South Side

View NZ$147 flight on Tue, 18 Aug 2026Opens in a new window

Flight 1

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  • Alaska Airlines

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Cheap Tickets to South Side

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 19 May - Wed, 3 June
BOS
Boston
ORD
Chicago
NZ$288 Return, found 8 hours ago
NZ$288
Return
found 8 hours ago
Select Delta flight, departing Tue, 19 May from Boston to Chicago, returning Wed, 3 June, priced at NZ$288 found 8 hours ago
Delta
Thu, 21 May - Wed, 3 June
BOS
Boston
ORD
Chicago
NZ$297 Return, found 8 hours ago
NZ$297
Return
found 8 hours ago
Select Delta flight, departing Thu, 21 May from Boston to Chicago, returning Wed, 3 June, priced at NZ$297 found 8 hours ago
American Airlines
Fri, 22 May - Fri, 29 May
BOS
Boston
ORD
Chicago
NZ$337 Return, found 3 days ago
NZ$337
Return
found 3 days ago
Select American Airlines flight, departing Fri, 22 May from Boston to Chicago, returning Fri, 29 May, priced at NZ$337 found 3 days ago
United
Fri, 1 May - Sat, 16 May
BOS
Boston
ORD
Chicago
NZ$433 Return, found 8 hours ago
NZ$433
Return
found 8 hours ago
Select United flight, departing Fri, 1 May from Boston to Chicago, returning Sat, 16 May, priced at NZ$433 found 8 hours ago
Alaska Airlines
Fri, 22 May - Fri, 29 May
BOS
Boston
ORD
Chicago
NZ$1,044 Return, found 3 days ago
NZ$1,044
Return
found 3 days ago
Select Alaska Airlines flight, departing Fri, 22 May from Boston to Chicago, returning Fri, 29 May, priced at NZ$1,044 found 3 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 NZ$288.
How much is a flight to South Side?
In the last seven days, return tickets to South Side sold from just NZ$288 and reached a maximum price of NZ$2,245. For one-way journeys departing from Boston (BOS), the lowest price during this time was only NZ$147.
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 NZ$288 and NZ$2,245. 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
NZ$423

Trending flights to South Side

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Tahiti Nui
Sun, 14 June - Tue, 16 June
AKL
Auckland
ORD
Chicago
NZ$2,245 Return, found 13 hours ago
NZ$2,245
Return
found 13 hours ago
Select Air Tahiti Nui flight, departing Sun, 14 June from Auckland to Chicago, returning Tue, 16 June, priced at NZ$2,245 found 13 hours ago

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