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Cheap flights from Wales to Chicago Midway Airport from £314

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
23 May — 30 May1
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 23 April 2026.

Tue 2/608:25
BRS
-
MDW
2 stops15h 31m
Multiple Airlines
Tue 9/609:54
MDW
-
BRS
2 stops24h 06m
Multiple Airlines
Deal found 17/4£605
Tue 19/507:30
MAN
-
MDW
2 stops32h 15m
Multiple Airlines
Tue 26/515:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 19/4£658
Mon 21/920:50
MAN
-
MDW
2 stops27h 41m
Virgin Atlantic
Mon 28/913:00
MDW
-
MAN
2 stops19h 00m
Virgin Atlantic
Deal found 20/4£696
Mon 21/913:00
MAN
-
MDW
1 stop14h 46m
Air France
Mon 28/917:59
MDW
-
MAN
2 stops14h 01m
Air France
Deal found 20/4£704
Mon 21/913:00
MAN
-
MDW
1 stop14h 46m
Delta
Tue 6/1017:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 21/4£727
Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/909:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 20/4£730
Sun 20/920:45
MAN
-
MDW
2 stops27h 46m
Virgin Atlantic
Mon 5/1018:45
MDW
-
MAN
2 stops16h 00m
Virgin Atlantic
Deal found 21/4£730
Fri 4/913:00
MAN
-
MDW
1 stop14h 46m
Multiple Airlines
Tue 8/913:00
MDW
-
MAN
2 stops15h 20m
Multiple Airlines
Deal found 20/4£738
Fri 4/905:55
MAN
-
MDW
2 stops18h 10m
KLM
Tue 8/913:00
MDW
-
MAN
2 stops15h 20m
KLM
Deal found 20/4£742
Wed 2/909:20
BRS
-
MDW
2 stops14h 45m
Delta
Wed 23/910:35
MDW
-
BRS
2 stops16h 15m
Delta
Deal found 20/4£742
Wed 6/510:40
MAN
-
MDW
1 stop17h 48m
Virgin Atlantic
Tue 12/510:59
MDW
-
MAN
1 stop15h 51m
Virgin Atlantic
Deal found 20/4£744
Sat 7/1113:25
MAN
-
MDW
1 stop14h 20m
Virgin Atlantic
Fri 13/1113:00
MDW
-
MAN
2 stops26h 30m
Virgin Atlantic
Deal found 20/4£748

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 23 April 2026.

Round-trip from

£605

One-way from

£314
2/6-9/6
  • 2/6-9/6
  • 4 total stops
  • 39h 37m total
  • Wales to Chicago
Search Deals
1/5
  • 1/5
  • 3 total stops
  • 40h 45m 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 23 April 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
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 9/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Wed 14/10

13:05-07:15

1 stop12h 10m

£759

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Wed 23/9

13:00-08:15

2 stops13h 15m

£763

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 15/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Tue 20/10

17:59-14:00

2 stops14h 01m

£807

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 19/5

06:15-18:33

2 stops18h 18m

Chicago Midway

Tue 26/5

19:13-17:00

2 stops15h 47m

£815

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 28/5

09:20-18:33

2 stops15h 13m

Chicago Midway

Tue 30/6

13:16-08:50

2 stops13h 34m

£825

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 18/6

06:15-18:31

2 stops18h 16m

Chicago Midway

Mon 29/6

18:58-17:00

2 stops16h 02m

£845

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 29/6

06:15-18:18

2 stops18h 03m

Chicago Midway

Tue 7/7

13:16-10:15

2 stops14h 59m

£847

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 4/6

17:15-18:33

2 stops31h 18m

Chicago Midway

Thu 11/6

13:16-09:15

2 stops13h 59m

£865

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Sat 6/6

17:35-18:31

2 stops30h 56m

Chicago Midway

Sat 13/6

18:35-16:45

2 stops16h 10m

£895

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 9/7

17:15-18:18

2 stops31h 03m

Chicago Midway

Thu 16/7

09:20-09:15

2 stops17h 55m

£898

Flights are sorted by cheapest return flights first.

Deals found on 19/4

Showing 1-10 of 27 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 £759, Delta can have you in Chicago Midway Airport from Wales in 14h 45m. 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?

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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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