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Cheap flights from Wales to Chicago Midway Airport from £255

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
8 May — 15 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 8 April 2026.

Mon 4/505:55
MAN
-
MDW
2 stops18h 03m
Delta
Tue 12/513:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 5/4£717
Wed 6/510:40
MAN
-
MDW
1 stop17h 48m
Delta
Wed 13/513:22
MDW
-
MAN
2 stops12h 53m
Delta
Deal found 5/4£719
Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/909:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 5/4£720
Wed 13/506:15
BRS
-
MDW
2 stops18h 18m
KLM
Wed 20/509:23
MDW
-
BRS
2 stops17h 27m
KLM
Deal found 5/4£720
Tue 21/413:00
MAN
-
MDW
1 stop15h 28m
Virgin Atlantic
Tue 28/410:41
MDW
-
MAN
1 stop16h 09m
Virgin Atlantic
Deal found 4/4£735
Thu 7/509:45
CWL
-
MDW
2 stops14h 48m
KLM
Tue 12/519:13
MDW
-
CWL
2 stops15h 32m
KLM
Deal found 4/4£735
Tue 19/509:45
CWL
-
MDW
2 stops14h 48m
KLM
Tue 26/513:22
MDW
-
CWL
2 stops13h 53m
KLM
Deal found 4/4£741
Fri 9/1013:00
MAN
-
MDW
1 stop14h 45m
Delta
Wed 14/1017:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 6/4£746
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£750
Mon 11/513:00
MAN
-
MDW
1 stop14h 09m
Delta
Mon 18/509:22
MDW
-
MAN
2 stops16h 53m
Delta
Deal found 7/4£752
Wed 20/506:15
BRS
-
MDW
2 stops17h 41m
Delta
Wed 27/509:23
MDW
-
BRS
2 stops17h 27m
Delta
Deal found 5/4£763
Tue 19/506:15
BRS
-
MDW
2 stops17h 41m
Delta
Tue 26/513:22
MDW
-
BRS
2 stops17h 53m
Delta
Deal found 4/4£764

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 8 April 2026.

Round-trip from

£708

One-way from

£255
18/5-25/5
  • 18/5-25/5
  • 4 total stops
  • 44h 49m 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 8 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

09:30-08:15

2 stops16h 45m

£720

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 7/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Mon 14/9

18:45-16:45

2 stops16h 00m

£720

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 7/5

09:45-18:33

2 stops14h 48m

Chicago Midway

Tue 12/5

19:13-16:45

2 stops15h 32m

£735

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Tue 19/5

09:45-18:33

2 stops14h 48m

Chicago Midway

Tue 26/5

13:22-09:15

2 stops13h 53m

£741

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 20/5

06:15-17:56

2 stops17h 41m

Chicago Midway

Wed 27/5

09:23-08:50

2 stops17h 27m

£763

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 19/5

06:15-17:56

2 stops17h 41m

Chicago Midway

Tue 26/5

13:22-13:15

2 stops17h 53m

£764

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 28/4

06:15-17:58

2 stops17h 43m

Chicago Midway

Mon 1/6

19:13-17:00

2 stops15h 47m

£814

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 2/6

13:00-21:09

1 stop14h 09m

Chicago Midway

Tue 9/6

09:17-08:20

2 stops17h 03m

£817

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 19/5

13:00-21:09

1 stop14h 09m

Chicago Midway

Tue 26/5

09:22-08:50

2 stops17h 28m

£818

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 30/6

05:55-16:46

2 stops16h 51m

Chicago Midway

Tue 7/7

13:16-10:05

2 stops14h 49m

£823

Flights are sorted by cheapest return flights first.

Deals found on 7/4

Showing 1-10 of 40 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 £818, Delta can have you in Chicago Midway Airport from Wales in 14h 09m. 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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