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Cheap flights from Wales to Chicago Midway Airport from £266

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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
28 May — 4 Jun1
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 28 April 2026.

Tue 26/511:35
CWL
-
MDW
1 stop28h 10m
Multiple Airlines
Tue 2/619:13
MDW
-
CWL
2 stops33h 02m
Multiple Airlines
Deal found 26/4£709
Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/909:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 24/4£727
Wed 9/910:40
MAN
-
MDW
2 stops28h 02m
Delta
Tue 15/906:00
MDW
-
MAN
2 stops20h 20m
Delta
Deal found 27/4£729
Mon 7/905:55
MAN
-
MDW
2 stops18h 10m
Delta
Tue 15/913:00
MDW
-
MAN
2 stops13h 25m
Delta
Deal found 26/4£730
Wed 28/1005:50
MAN
-
MDW
2 stops20h 55m
Virgin Atlantic
Wed 11/1109:30
MDW
-
MAN
2 stops15h 10m
Virgin Atlantic
Deal found 27/4£735
Sat 12/913:15
MAN
-
MDW
1 stop14h 31m
Virgin Atlantic
Thu 24/913:05
MDW
-
MAN
1 stop13h 45m
Virgin Atlantic
Deal found 25/4£751
Thu 17/913:00
MAN
-
MDW
1 stop14h 46m
Delta
Mon 28/917:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 27/4£756
Fri 9/1013:00
MAN
-
MDW
1 stop14h 45m
Delta
Wed 14/1009:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 25/4£757
Fri 9/1013:00
MAN
-
MDW
1 stop26h 52m
Multiple Airlines
Mon 12/1006:00
MDW
-
MAN
1 stop20h 50m
Multiple Airlines
Deal found 27/4£758
Mon 8/609:20
BRS
-
MDW
2 stops14h 58m
KLM
Mon 22/612:45
MDW
-
BRS
2 stops14h 05m
KLM
Deal found 27/4£803
Tue 26/509:45
CWL
-
MDW
2 stops14h 48m
Delta
Tue 2/618:36
MDW
-
CWL
2 stops16h 09m
Delta
Deal found 26/4£834
Tue 9/606:15
BRS
-
MDW
2 stops18h 03m
Delta
Tue 16/617:11
MDW
-
BRS
2 stops17h 49m
Delta
Deal found 25/4£862

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 28 April 2026.

Round-trip from

£709

One-way from

£266
WestJet
  • WestJet
  • 26/5-2/6
  • 3 total stops
  • 61h 12m total
  • Wales to Chicago
Search Deals
17/5
  • 17/5
  • 2 total stops
  • 54h 15m 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 28 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

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Tue 26/5

11:35-09:45

1 stop28h 10m

Chicago Midway

Tue 2/6

19:13-10:15

2 stops33h 02m

£709

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-08:42

2 stops28h 02m

Chicago Midway

Wed 16/9

06:00-08:15

2 stops20h 15m

£729

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-21:46

1 stop17h 06m

Chicago Midway

Mon 14/9

06:00-08:15

2 stops20h 15m

£729

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 5/10

05:55-18:31

2 stops18h 36m

Chicago Midway

Sun 18/10

13:00-10:20

2 stops15h 20m

£758

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 6/10

05:55-18:37

2 stops18h 42m

Chicago Midway

Sun 18/10

13:00-10:20

2 stops15h 20m

£758

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-08:42

2 stops28h 02m

Chicago Midway

Sun 13/9

17:59-22:00

2 stops22h 01m

£759

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-08:42

2 stops28h 02m

Chicago Midway

Sat 19/9

16:30-07:15

1 stop32h 45m

£759

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 5/10

05:55-18:31

2 stops18h 36m

Chicago Midway

Sat 17/10

13:00-08:15

2 stops13h 15m

£760

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 8/6

09:20-18:18

2 stops14h 58m

Chicago Midway

Mon 22/6

12:45-08:50

2 stops14h 05m

£803
Fastest return journey

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

£804

Flights are sorted by cheapest return flights first.

Deals found on 24/4

Showing 1-10 of 34 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 £803, Delta can have you in Chicago Midway Airport from Wales in 14h 58m. The distance between Wales and Chicago Midway Airport is about 3858 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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