£323 Cheap Flights to Southwest Side

View £323 flight on Wed, 10 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 £323 for one-way flights and £366 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.

Aer Lingus
Sat, 7 Feb - Sun, 8 Feb
LHR
London
ORD
Chicago
£366 Return, found 1 day ago
£366
Return
found 1 day ago
Select Aer Lingus flight, departing Sat, 7 Feb from London to Chicago, returning Sun, 8 Feb, priced at £366 found 1 day ago
Icelandair
Thu, 25 Sep - Thu, 2 Oct
LGW
London
ORD
Chicago
£369 Return, found 16 hours ago
£369
Return
found 16 hours ago
Select Icelandair flight, departing Thu, 25 Sep from London to Chicago, returning Thu, 2 Oct, priced at £369 found 16 hours ago
TAP Portugal
Wed, 22 Oct - Sun, 26 Oct
LGW
London
ORD
Chicago
£399 Return, found 1 hour ago
£399
Return
found 1 hour ago
Select TAP Portugal flight, departing Wed, 22 Oct from London to Chicago, returning Sun, 26 Oct, priced at £399 found 1 hour ago
Scandinavian Airlines
Thu, 27 Nov - Mon, 1 Dec
MAN
Manchester
ORD
Chicago
£409 Return, found 5 days ago
£409
Return
found 5 days ago
Select Scandinavian Airlines flight, departing Thu, 27 Nov from Manchester to Chicago, returning Mon, 1 Dec, priced at £409 found 5 days ago
Swiss International Air Lines
Sat, 10 Jan - Sat, 17 Jan
LCY
London
ORD
Chicago
£439 Return, found 5 days ago
£439
Return
found 5 days ago
Select Swiss International Air Lines flight, departing Sat, 10 Jan from London to Chicago, returning Sat, 17 Jan, priced at £439 found 5 days ago

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

August is typically the cheapest month to fly

From £72 - £446 per traveller.

Graph displaying average flight prices per month

Expedia 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 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 Southwest Side.

Expedia is the largest online travel agency which means that Expedia have access to cheap flights. So make sure you check Expedia regularly for these bargain flights because the cheapest airline tickets 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. If you need additional assistance, Expedia Customer Service representatives are available from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends. Our capable staff will be able to help you with any questions regarding your Southwest Side flight, or other booking questions that may arise. When you book flights with Expedia you can rest assured that you have booked the best flight at the lowest price.

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 £366. 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 London (LGW), you could've locked in an affordable ticket for just £323 in the last seven days. Round-trip journeys to Southwest Side ranged from only £366 to £604 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.
When is the cheapest time to fly to Southwest Side?
If you'd rather spend your hard-earned holiday money getting to know Southwest Side rather than on getting there, depart earlier in the week. The most affordable day to travel is normally Tuesday, with Monday running a close second. With many people keeping their travel to weekends, Saturday often has the costliest ticket prices.
How much is a plane ticket to Southwest Side?
Seats to Southwest Side ranged from £366 to £604 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
£366

Trending flights to Southwest Side

Prices were available within the past 7 days and start at £323 for one-way flights and £366 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.

Aer Lingus
Sat, 7 Feb - Sun, 8 Feb
LHR
London
ORD
Chicago
£366 Return, found 1 day ago
£366
Return
found 1 day ago
Select Aer Lingus flight, departing Sat, 7 Feb from London to Chicago, returning Sun, 8 Feb, priced at £366 found 1 day ago
*Available to Expedia members.