Cheap Flights to Southwest Side

View ฿2,245 flight on Wed, 17 Sep 2025Opens in a new window

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Cheap round-trip flights to Southwest Side

Prices were available within the past 7 days and start at ฿2,245 for one-way flights and ฿4,510 for round trip, for the period specified. Be sure to select the 'Direct flights only' box above if you are looking for a non stop route. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, 31 Aug - Fri, 5 Sep
BOS
Boston
ORD
Chicago
฿4,510 Return, found 1 day ago
฿4,510
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Boston to Chicago, returning Fri, 5 Sep, priced at ฿4,510 found 1 day ago
United
Thu, 4 Sep - Thu, 11 Sep
BOS
Boston
ORD
Chicago
฿6,435 Return, found 6 days ago
฿6,435
Return
found 6 days ago
Select United flight, departing Thu, 4 Sep from Boston to Chicago, returning Thu, 11 Sep, priced at ฿6,435 found 6 days ago
American Airlines
Sun, 31 Aug - Fri, 5 Sep
BOS
Boston
ORD
Chicago
฿6,805 Return, found 1 day ago
฿6,805
Return
found 1 day ago
Select American Airlines flight, departing Sun, 31 Aug from Boston to Chicago, returning Fri, 5 Sep, priced at ฿6,805 found 1 day ago
China Airlines
Tue, 28 Apr - Tue, 12 May
BKK
Bangkok
ORD
Chicago
฿29,305 Return, found 3 days ago
฿29,305
Return
found 3 days ago
Select China Airlines flight, departing Tue, 28 Apr from Bangkok to Chicago, returning Tue, 12 May, priced at ฿29,305 found 3 days ago
Korean Air
Thu, 11 Sep - Sun, 14 Sep
BKK
Bangkok
ORD
Chicago
฿33,380 Return, just found
฿33,380
Return
just found
Select Korean Air flight, departing Thu, 11 Sep from Bangkok to Chicago, returning Sun, 14 Sep, priced at ฿33,380 just found

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

August is typically the cheapest month to fly

From ฿3,485 - ฿17,917 per traveller.

Graph displaying average flight prices per month

Flights to Southwest Side

Searching for cheap flights to Southwest Side? No travel company presents more choices than Expedia if you're looking to compare flights to Southwest 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 Southwest Side. Expedia provides the cheapest flights to Southwest Side and you may find even greater savings if you combine your flight to Southwest Side with a hotel stay. Travellers who are flexible about flight times can benefit from last minute cheap flights to Southwest Side.

Expedia is the largest online travel agency which means that Expedia have access to cheap airline tickets. So make sure you check Expedia regularly for these bargain flights because the cheapest airline ticket deals sell out fast.

Expedia is not only free for everyone to use but it quick and easy to use. Find the lowest flight prices guaranteed and book directly through Expedia. Browse through hundreds of cheap flight offers to find the one that suits your budget by simply inputting your travel dates. Expedia will then find the cheapest flights to Southwest Side for that period and let you choose your preferred time and airline.

Frequently asked questions

How do I find cheap flights to Southwest Side that have flexible change policies?
At Expedia, we've been channeling our inner gymnast to give you the most flexible airfares available. Simply click on "No change fee" directly below the filter heading "Flexible change policies" to find the best flights to Southwest Side.
Which airlines fly to Southwest Side?
With a great selection of airlines offering flights into or near Southwest Side, you have plenty of choice:

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

How can I find cheap tickets to Southwest Side?
One of the best ways to bag cheap tickets to Southwest Side is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. It will reveal the cheapest prices for nearby days. The lowest price for a flight to Southwest Side in the last seven days was ฿4,510. Booking well in advance will generally help you get an even bigger bargain.
How much is a flight to Southwest Side?
If you were flying one way from Boston (BOS), you could've locked in an affordable ticket for just ฿2,245 in the last seven days. Round-trip journeys to Southwest Side ranged from only ฿4,510 to ฿33,380 during this same period.
What are the most popular airports to fly into in Southwest Side?
Pack your bags and jet into O'Hare Intl. Airport (ORD), Southwest Side's primary flight hub. Secure a seat on one of the 25,318 flights that land at this favourite destination every month.
How much is a plane ticket to Southwest Side?
Seats to Southwest Side ranged from ฿4,510 to ฿33,380 in the last seven days. Usually, the sooner you book the better the price.
What months are the cheapest to book a flight to Southwest Side?
February is the best month to secure a seat for your Southwest Side holiday. Airfares are at their most expensive throughout the busy month of December, so keep clear of this time if you can.
Flights to Southwest Side information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
฿6,425

Trending flights to Southwest Side

Prices were available within the past 7 days and start at ฿2,245 for one-way flights and ฿4,510 for round trip, for the period specified. Be sure to select the 'Direct flights only' box above if you are looking for a non stop route. Prices and availability are subject to change. Additional terms apply.

China Airlines
Tue, 28 Apr - Tue, 12 May
BKK
Bangkok
ORD
Chicago
฿29,305 Return, found 3 days ago
฿29,305
Return
found 3 days ago
Select China Airlines flight, departing Tue, 28 Apr from Bangkok to Chicago, returning Tue, 12 May, priced at ฿29,305 found 3 days ago
*Available to Expedia members.