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Cheap flights from Wales to Chicago Midway Airport from £268

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
28 Aug — 4 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Wales to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Wales to Midway
Explore the most affordable flight options available from Wales to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 July 2026.

Tue 8/906:15
BRS
-
MDW
2 stops18h 04m
Delta
Tue 15/919:13
MDW
-
BRS
2 stops15h 47m
Delta
Deal found 25/7£651
Mon 14/909:20
BRS
-
MDW
2 stops14h 59m
Delta
Mon 28/919:01
MDW
-
BRS
2 stops15h 59m
Delta
Deal found 27/7£652
Tue 8/909:45
CWL
-
MDW
2 stops18h 59m
Delta
Tue 15/909:29
MDW
-
CWL
2 stops17h 46m
Delta
Deal found 24/7£677
Wed 2/909:20
BRS
-
MDW
2 stops14h 41m
Delta
Sat 12/917:37
MDW
-
BRS
2 stops17h 23m
Delta
Deal found 29/7£681
Mon 31/820:50
MAN
-
MDW
2 stops26h 09m
Virgin Atlantic
Wed 9/909:29
MDW
-
MAN
2 stops16h 56m
Virgin Atlantic
Deal found 25/7£700
Wed 7/1005:55
MAN
-
MDW
2 stops18h 05m
Virgin Atlantic
Wed 14/1009:29
MDW
-
MAN
2 stops16h 56m
Virgin Atlantic
Deal found 27/7£700
Mon 2/1105:50
MAN
-
MDW
2 stops18h 10m
Delta
Thu 5/1112:27
MDW
-
MAN
2 stops15h 38m
Delta
Deal found 27/7£720
Wed 16/905:55
MAN
-
MDW
2 stops18h 38m
Delta
Wed 23/919:01
MDW
-
MAN
2 stops15h 44m
Delta
Deal found 29/7£730
Sat 31/1006:00
MAN
-
MDW
2 stops17h 00m
Virgin Atlantic
Thu 5/1109:29
MDW
-
MAN
2 stops16h 51m
Virgin Atlantic
Deal found 27/7£735
Wed 7/1009:45
CWL
-
MDW
2 stops18h 48m
KLM
Sun 11/1010:01
MDW
-
CWL
2 stops17h 14m
KLM
Deal found 27/7£737
Tue 8/905:55
MAN
-
MDW
2 stops17h 02m
Virgin Atlantic
Wed 2/1213:05
MDW
-
MAN
2 stops15h 40m
Virgin Atlantic
Deal found 24/7£742
Sat 5/905:55
MAN
-
MDW
2 stops17h 04m
Virgin Atlantic
Tue 15/909:29
MDW
-
MAN
2 stops18h 41m
Virgin Atlantic
Deal found 28/7£761

Find flight deals from Wales to Midway

Keep the following information in mind while searching for Wales to Midway flight deals. Data was last updated 29 July 2026.

Round-trip from

£648

One-way from

£268
Delta
  • Delta
  • 21/9-5/10
  • 4 total stops
  • 34h 05m total
  • Wales to Chicago
Search Deals
25/8
  • 25/8
  • 3 total stops
  • 44h 50m total
  • Wales to Chicago
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Wales to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 29 July 2026.
Use the filters below to find and compare flights from Wales to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 8/9

06:15-18:19

2 stops18h 04m

Chicago Midway

Tue 15/9

19:13-17:00

2 stops15h 47m

£651

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 5/10

09:20-18:19

2 stops14h 59m

Chicago Midway

Thu 15/10

17:31-13:15

2 stops13h 44m

£652

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 14/9

09:20-18:19

2 stops14h 59m

Chicago Midway

Mon 28/9

19:01-17:00

2 stops15h 59m

£652

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Tue 8/9

09:45-22:44

2 stops18h 59m

Chicago Midway

Tue 15/9

09:29-09:15

2 stops17h 46m

£677

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 2/9

09:20-18:01

2 stops14h 41m

Chicago Midway

Sat 12/9

17:37-17:00

2 stops17h 23m

£681

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-18:19

2 stops18h 24m

Chicago Midway

Wed 23/9

19:01-16:45

2 stops15h 44m

£732

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 8/9

05:55-16:57

2 stops17h 02m

Chicago Midway

Wed 2/12

13:05-10:45

2 stops15h 40m

£742

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 5/10

05:55-18:19

2 stops18h 24m

Chicago Midway

Sun 18/10

13:27-10:10

2 stops14h 43m

£762

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 8/10

05:55-16:47

2 stops16h 52m

Chicago Midway

Sun 11/10

12:27-10:10

2 stops15h 43m

£791

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 25/9

08:55-18:19

2 stops15h 24m

Chicago Midway

Sat 3/10

13:19-08:25

2 stops13h 06m

£794

Flights are sorted by cheapest return flights first.

Deals found on 27/7

Showing 1-10 of 26 resultsSorted by cheapest first
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Best time to book a flight from Wales to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Wales with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Wales to Chicago Midway Airport

No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Wales to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Wales to Chicago Midway Airport?

    For as low as £742, Delta can have you in Chicago Midway Airport from Wales in 17h 02m. The distance between Wales and Chicago Midway Airport is about 3816 mi. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most popular routes from Wales to Chicago Midway Airport?

    The most popular route from Wales to Chicago Midway Airport is Manchester - Chicago Midway. You may also consider Bristol - Chicago Midway or Cardiff Wales - Chicago Midway.

  • Can I find deals for flights from Wales to Midway that include hotel bookings?

    Yes. In addition to deals on Wales to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Wales to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wales to Midway.

  • Can I find deals for business class flights from Wales to Midway?

    Yes. Cheapflights offers flight deals from Wales to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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How does Cheapflights help users find flights from Wales to Midway?

Cheapflights makes it easy to find Wales to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Wales to Midway?

Millions of users choose and trust Cheapflights to book the best flight deals from Wales to Midway for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Wales to Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Wales to Midway with no change fees.

Can Cheapflights notify me if prices for flights from Wales to Midway become cheaper?

Not ready to book yet? You can track prices for flights from Wales to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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