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Cheap flights from Wales to Chicago Midway Airport from £301

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 27/4. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
23 Apr — 30 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 24 March 2026.

Sun 19/417:30
MAN
-
MDW
2 stops31h 06m
Virgin Atlantic
Sun 26/413:24
MDW
-
MAN
2 stops36h 51m
Virgin Atlantic
Deal found 22/3£670
Tue 10/1113:30
MAN
-
MDW
1 stop14h 15m
Virgin Atlantic
Tue 24/1113:00
MDW
-
MAN
2 stops13h 20m
Virgin Atlantic
Deal found 21/3£672
Mon 4/509:20
BRS
-
MDW
2 stops15h 16m
KLM
Mon 11/513:22
MDW
-
BRS
2 stops13h 28m
KLM
Deal found 19/3£681
Tue 5/509:45
CWL
-
MDW
2 stops18h 43m
KLM
Tue 12/519:13
MDW
-
CWL
2 stops15h 32m
KLM
Deal found 21/3£682
Tue 5/509:20
BRS
-
MDW
2 stops15h 16m
KLM
Tue 12/513:22
MDW
-
BRS
2 stops13h 28m
KLM
Deal found 21/3£683
Mon 20/409:20
BRS
-
MDW
2 stops15h 16m
KLM
Mon 27/412:52
MDW
-
BRS
2 stops13h 58m
KLM
Deal found 23/3£687
Wed 29/410:40
MAN
-
MDW
1 stop17h 48m
Virgin Atlantic
Sat 2/517:21
MDW
-
MAN
1 stop31h 54m
Virgin Atlantic
Deal found 20/3£688
Mon 27/413:00
MAN
-
MDW
1 stop15h 28m
Delta
Thu 7/513:22
MDW
-
MAN
2 stops18h 38m
Delta
Deal found 24/3£696
Wed 6/509:45
CWL
-
MDW
2 stops18h 43m
Delta
Wed 13/509:23
MDW
-
CWL
2 stops17h 52m
Delta
Deal found 22/3£696
Wed 6/506:15
BRS
-
MDW
2 stops17h 43m
Delta
Wed 13/509:23
MDW
-
BRS
2 stops17h 27m
Delta
Deal found 22/3£697
Mon 20/405:55
MAN
-
MDW
2 stops18h 03m
Delta
Mon 27/413:24
MDW
-
MAN
2 stops13h 26m
Delta
Deal found 21/3£700
Tue 5/513:00
MAN
-
MDW
1 stop15h 28m
Multiple Airlines
Tue 12/513:22
MDW
-
MAN
2 stops13h 03m
Multiple Airlines
Deal found 21/3£704

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 24 March 2026.

Round-trip from

£670

One-way from

£301
Virgin Atlantic
  • Virgin Atlantic
  • 19/4-26/4
  • 4 total stops
  • 67h 57m total
  • Wales to Chicago
Search Deals
27/4
  • 27/4
  • 3 total stops
  • 35h 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 24 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
Fastest return journey

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 4/5

09:20-18:36

2 stops15h 16m

Chicago Midway

Mon 11/5

13:22-08:50

2 stops13h 28m

£681

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 6/5

09:45-22:28

2 stops18h 43m

Chicago Midway

Wed 13/5

09:23-09:15

2 stops17h 52m

£696

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 6/5

06:15-17:58

2 stops17h 43m

Chicago Midway

Wed 13/5

09:23-08:50

2 stops17h 27m

£697

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 6/5

05:55-17:58

2 stops18h 03m

Chicago Midway

Wed 13/5

13:59-10:00

2 stops14h 01m

£705

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Wed 23/9

10:35-08:15

2 stops15h 40m

£709

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Mon 4/5

17:15-18:36

2 stops31h 21m

Chicago Midway

Mon 11/5

19:13-16:45

2 stops15h 32m

£722

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Mon 20/4

17:15-17:58

2 stops30h 43m

Chicago Midway

Mon 27/4

09:29-09:15

2 stops17h 46m

£723

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Mon 4/5

09:45-22:28

2 stops18h 43m

Chicago Midway

Mon 11/5

09:22-09:15

2 stops17h 53m

£736

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Sat 18/4

17:35-17:58

2 stops30h 23m

Chicago Midway

Sat 25/4

09:46-16:45

2 stops24h 59m

£755

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 18/9

13:00-21:46

1 stop14h 46m

Chicago Midway

Sun 27/9

17:59-14:00

2 stops14h 01m

£764

Flights are sorted by cheapest return flights first.

Deals found on 20/3

Showing 1-10 of 44 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 £681, Virgin Atlantic can have you in Chicago Midway Airport from Wales in 15h 16m. 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 Cardiff Wales - Chicago Midway or Bristol - 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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