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Cheap flights from Wales to Chicago Midway Airport from £331

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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
15 May — 22 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 15 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£691
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£724
Mon 11/505:55
MAN
-
MDW
2 stops18h 01m
Delta
Mon 18/513:22
MDW
-
MAN
2 stops12h 53m
Delta
Deal found 11/4£725
Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/909:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 13/4£725
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£730
Sat 9/517:25
MAN
-
MDW
2 stops51h 10m
Multiple Airlines
Thu 21/515:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 10/4£743
Fri 9/1013:00
MAN
-
MDW
1 stop14h 45m
Delta
Wed 14/1009:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 10/4£752
Fri 8/509:20
BRS
-
MDW
2 stops15h 13m
KLM
Thu 28/513:22
MDW
-
BRS
2 stops13h 28m
KLM
Deal found 14/4£799
Wed 27/509:45
CWL
-
MDW
2 stops14h 48m
Multiple Airlines
Wed 3/613:22
MDW
-
CWL
2 stops13h 53m
Multiple Airlines
Deal found 12/4£810
Sat 9/510:45
BRS
-
MDW
2 stops13h 48m
KLM
Sat 16/519:13
MDW
-
BRS
2 stops20h 52m
KLM
Deal found 11/4£814
Fri 8/506:15
BRS
-
MDW
2 stops17h 41m
Delta
Thu 28/509:22
MDW
-
BRS
2 stops17h 28m
Delta
Deal found 14/4£818
Mon 25/506:15
BRS
-
MDW
2 stops17h 41m
Delta
Mon 1/609:23
MDW
-
BRS
2 stops17h 27m
Delta
Deal found 10/4£832

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 15 April 2026.

Round-trip from

£691

One-way from

£331
9/5-17/5
  • 9/5-17/5
  • 2 total stops
  • 40h 40m total
  • Wales to Chicago
Search Deals
29/4
  • 29/4
  • 3 total stops
  • 31h 16m 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 15 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

£725

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 9/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Wed 14/10

09:30-08:15

2 stops16h 45m

£754

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 27/5

09:45-18:33

2 stops14h 48m

Chicago Midway

Wed 3/6

13:22-09:15

2 stops13h 53m

£810

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sat 9/5

05:55-18:33

2 stops18h 38m

Chicago Midway

Sat 16/5

13:22-08:50

2 stops13h 28m

£816

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 8/5

05:55-18:33

2 stops18h 38m

Chicago Midway

Mon 18/5

13:22-08:15

2 stops12h 53m

£818

BristolChicago

BRS - MDW

BRSMDW

Bristol

Fri 8/5

06:15-17:56

2 stops17h 41m

Chicago Midway

Thu 28/5

09:22-08:50

2 stops17h 28m

£818

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

£823

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 7/7

13:00-22:15

1 stop15h 15m

Chicago Midway

Tue 21/7

13:16-10:20

2 stops15h 04m

£824

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 30/6

05:55-16:46

2 stops16h 51m

Chicago Midway

Thu 9/7

13:49-10:05

2 stops14h 16m

£826

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 30/4

12:10-22:28

2 stops16h 18m

Chicago Midway

Wed 6/5

13:24-10:10

2 stops14h 46m

£827

Flights are sorted by cheapest return flights first.

Deals found on 11/4

Showing 1-10 of 39 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 £869, Delta can have you in Chicago Midway Airport from Wales in 14h 48m. The distance between Wales and Chicago Midway Airport is about 3833 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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