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Cheap flights from Wales to Chicago Midway Airport from £300

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 17/6. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
9 Apr — 16 Apr1
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 10 March 2026.

Tue 21/409:45
CWL
-
MDW
2 stops38h 13m
Virgin Atlantic
Tue 28/409:27
MDW
-
CWL
2 stops17h 48m
Virgin Atlantic
Deal found 7/3£656
Mon 20/406:15
BRS
-
MDW
2 stops17h 43m
Delta
Mon 27/419:16
MDW
-
BRS
2 stops15h 44m
Delta
Deal found 6/3£659
Mon 20/413:00
MAN
-
MDW
1 stop15h 28m
Delta
Mon 27/413:24
MDW
-
MAN
2 stops12h 51m
Delta
Deal found 6/3£660
Wed 22/409:20
BRS
-
MDW
2 stops15h 16m
Delta
Wed 29/409:29
MDW
-
BRS
2 stops17h 21m
Delta
Deal found 7/3£660
Tue 14/420:50
MAN
-
MDW
2 stops27h 08m
Virgin Atlantic
Mon 20/413:24
MDW
-
MAN
2 stops12h 51m
Virgin Atlantic
Deal found 7/3£662
Wed 22/410:40
MAN
-
MDW
1 stop17h 48m
Delta
Wed 29/410:41
MDW
-
MAN
2 stops15h 34m
Delta
Deal found 8/3£664
Mon 4/508:55
MAN
-
MDW
2 stops15h 41m
Delta
Tue 12/518:36
MDW
-
MAN
2 stops13h 24m
Delta
Deal found 6/3£666
Mon 20/405:50
MAN
-
MDW
2 stops18h 46m
Virgin Atlantic
Mon 27/409:27
MDW
-
MAN
2 stops16h 58m
Virgin Atlantic
Deal found 7/3£667
Mon 7/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Tue 22/910:35
MDW
-
MAN
2 stops15h 45m
Delta
Deal found 7/3£671
Thu 17/913:00
MAN
-
MDW
1 stop14h 46m
Virgin Atlantic
Mon 28/913:00
MDW
-
MAN
2 stops13h 15m
Virgin Atlantic
Deal found 6/3£677
Fri 18/913:00
MAN
-
MDW
2 stops35h 31m
Multiple Airlines
Mon 28/910:35
MDW
-
MAN
2 stops15h 40m
Multiple Airlines
Deal found 6/3£680
Thu 17/910:55
MAN
-
MDW
2 stops37h 36m
Multiple Airlines
Mon 28/910:35
MDW
-
MAN
2 stops15h 40m
Multiple Airlines
Deal found 6/3£681

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 10 March 2026.

Round-trip from

£656

One-way from

£300
Virgin Atlantic
  • Virgin Atlantic
  • 21/4-28/4
  • 4 total stops
  • 56h 01m total
  • Wales to Chicago
Search Deals
17/6
  • 17/6
  • 3 total stops
  • 48h 50m 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 10 March 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

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 21/4

06:15-18:36

2 stops18h 21m

Chicago Midway

Tue 28/4

09:27-08:50

2 stops17h 23m

£659

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 20/4

06:15-17:58

2 stops17h 43m

Chicago Midway

Mon 27/4

19:16-17:00

2 stops15h 44m

£659
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 20/4

13:00-22:28

1 stop15h 28m

Chicago Midway

Mon 27/4

13:24-08:15

2 stops12h 51m

£660

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 22/4

09:20-18:36

2 stops15h 16m

Chicago Midway

Wed 29/4

09:29-08:50

2 stops17h 21m

£660

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 7/4

09:20-18:40

2 stops15h 20m

Chicago Midway

Tue 21/4

19:16-17:00

2 stops15h 44m

£686

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 23/4

09:45-17:58

2 stops38h 13m

Chicago Midway

Thu 30/4

09:27-16:45

2 stops25h 18m

£689

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 4/9

13:00-21:46

1 stop14h 46m

Chicago Midway

Mon 14/9

17:59-14:00

2 stops14h 01m

£696

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Sun 19/4

09:50-17:58

2 stops38h 08m

Chicago Midway

Sun 26/4

13:24-16:45

2 stops21h 21m

£704

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 1/9

05:50-18:31

2 stops18h 41m

Chicago Midway

Thu 10/9

17:59-14:00

2 stops14h 01m

£704

BristolChicago

BRS - MDW

BRSMDW

Bristol

Sun 19/4

06:15-17:58

2 stops17h 43m

Chicago Midway

Sun 26/4

09:27-08:50

2 stops17h 23m

£720

Flights are sorted by cheapest return flights first.

Deals found on 8/3

Showing 1-10 of 37 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 £659, KLM can have you in Chicago Midway Airport from Wales in 17h 43m. 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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