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Cheap flights from Wales to Chicago Midway Airport from £254

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 28/4. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
12 May — 19 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 12 April 2026.

Sat 9/513:25
MAN
-
MDW
1 stop26h 20m
Multiple Airlines
Sun 17/515:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 10/4£695
Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/909:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 7/4£718
Mon 11/513:00
MAN
-
MDW
1 stop14h 09m
Virgin Atlantic
Mon 18/513:22
MDW
-
MAN
2 stops12h 53m
Virgin Atlantic
Deal found 11/4£729
Mon 11/505:55
MAN
-
MDW
2 stops18h 01m
Delta
Mon 18/513:22
MDW
-
MAN
2 stops12h 53m
Delta
Deal found 11/4£729
Wed 28/1005:50
MAN
-
MDW
2 stops20h 55m
Virgin Atlantic
Tue 3/1110:35
MDW
-
MAN
2 stops14h 05m
Virgin Atlantic
Deal found 11/4£735
Fri 9/1013:00
MAN
-
MDW
1 stop14h 45m
Delta
Wed 14/1017:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 7/4£745
Thu 7/505:55
MAN
-
MDW
2 stops18h 38m
Virgin Atlantic
Thu 14/513:22
MDW
-
MAN
2 stops12h 58m
Virgin Atlantic
Deal found 7/4£748
Sat 9/513:25
MAN
-
MDW
1 stop26h 20m
Multiple Airlines
Thu 21/515:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 10/4£755
Sun 24/509:50
CWL
-
MDW
2 stops38h 43m
Virgin Atlantic
Sun 31/513:22
MDW
-
CWL
2 stops13h 53m
Virgin Atlantic
Deal found 9/4£799
Wed 13/506:15
BRS
-
MDW
2 stops17h 41m
Virgin Atlantic
Tue 19/513:22
MDW
-
BRS
2 stops17h 53m
Virgin Atlantic
Deal found 6/4£830
Mon 25/506:15
BRS
-
MDW
2 stops17h 41m
Delta
Mon 1/619:13
MDW
-
BRS
2 stops15h 47m
Delta
Deal found 10/4£837
Sat 23/507:30
CWL
-
MDW
3 stops17h 03m
Multiple Airlines
Sat 30/509:22
MDW
-
CWL
3 stops29h 58m
Multiple Airlines
Deal found 8/4£842

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 12 April 2026.

Round-trip from

£695

One-way from

£254
9/5-17/5
  • 9/5-17/5
  • 2 total stops
  • 40h 40m total
  • Wales to Chicago
Search Deals
28/4
  • 28/4
  • 3 total stops
  • 53h 46m 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 12 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

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Wed 23/9

13:00-10:20

2 stops15h 20m

£760

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Sun 24/5

09:50-18:33

2 stops38h 43m

Chicago Midway

Sun 31/5

13:22-09:15

2 stops13h 53m

£799

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 25/5

05:55-17:56

2 stops18h 01m

Chicago Midway

Mon 1/6

13:22-10:10

2 stops14h 48m

£828

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 26/5

13:00-21:09

1 stop14h 09m

Chicago Midway

Tue 2/6

09:22-08:50

2 stops17h 28m

£829

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 25/5

06:15-17:56

2 stops17h 41m

Chicago Midway

Mon 1/6

09:23-08:50

2 stops17h 27m

£837

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Sat 23/5

07:30-18:33

3 stops17h 03m

Chicago Midway

Sat 30/5

09:22-21:20

3 stops29h 58m

£842

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 13/5

06:15-18:33

2 stops18h 18m

Chicago Midway

Wed 20/5

09:23-08:50

2 stops17h 27m

£849

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 16/6

05:55-18:31

2 stops18h 36m

Chicago Midway

Sun 21/6

18:58-16:45

2 stops15h 47m

£859

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Sun 24/5

21:45-18:33

3 stops26h 48m

Chicago Midway

Sun 31/5

09:23-21:45

3 stops30h 22m

£865

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 18/5

06:15-18:33

2 stops18h 18m

Chicago Midway

Sun 24/5

18:36-17:00

2 stops16h 24m

£868

Flights are sorted by cheapest return flights first.

Deals found on 7/4

Showing 1-10 of 42 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 £760, Delta can have you in Chicago Midway Airport from Wales in 18h 36m. 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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