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Cheap flights from Wales to Chicago Midway Airport from £314

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 30/4. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
15 Feb — 22 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Wales to Midway

Keep the following information in mind while searching for Wales to Midway flight deals. Data was last updated 16 January 2026.

Round-trip from

£503

One-way from

£314
Virgin Atlantic
  • Virgin Atlantic
  • 11/2-18/2
  • 2 total stops
  • 29h 22m total
  • Wales to Chicago
Search Deals
30/4
  • 30/4
  • 3 total stops
  • 32h 45m total
  • Wales to Chicago
Search Deals

Find 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 16 January 2026.

Wed 11/213:00
MAN
-
MDW
1 stop15h 22m
Virgin Atlantic
Wed 18/212:45
MDW
-
MAN
1 stop14h 00m
Virgin Atlantic
Deal found 14/1£503
Wed 18/213:00
MAN
-
MDW
1 stop15h 31m
Virgin Atlantic
Wed 25/212:45
MDW
-
MAN
1 stop14h 00m
Virgin Atlantic
Deal found 14/1£503
Fri 30/113:25
MAN
-
MDW
1 stop14h 57m
Virgin Atlantic
Sun 22/213:28
MDW
-
MAN
2 stops14h 42m
Virgin Atlantic
Deal found 15/1£514
Sat 7/313:30
MAN
-
MDW
1 stop15h 01m
Virgin Atlantic
Thu 12/310:45
MDW
-
MAN
2 stops16h 10m
Virgin Atlantic
Deal found 14/1£518
Tue 24/213:30
MAN
-
MDW
1 stop15h 03m
Delta
Tue 3/313:49
MDW
-
MAN
2 stops14h 21m
Delta
Deal found 15/1£527
Mon 2/317:15
CWL
-
MDW
2 stops30h 22m
KLM
Mon 9/313:10
MDW
-
CWL
2 stops15h 40m
KLM
Deal found 16/1£528
Wed 11/213:00
MAN
-
MDW
1 stop15h 22m
Air France
Wed 18/218:40
MDW
-
MAN
2 stops33h 30m
Air France
Deal found 14/1£529
Thu 12/213:30
MAN
-
MDW
1 stop15h 01m
Virgin Atlantic
Thu 19/212:45
MDW
-
MAN
1 stop15h 45m
Virgin Atlantic
Deal found 15/1£529
Fri 6/213:25
MAN
-
MDW
1 stop14h 57m
Delta
Wed 11/212:46
MDW
-
MAN
2 stops15h 24m
Delta
Deal found 14/1£531
Thu 22/106:00
BRS
-
MDW
2 stops18h 36m
Delta
Wed 4/209:32
MDW
-
BRS
2 stops18h 43m
Delta
Deal found 14/1£534
Mon 13/405:55
MAN
-
MDW
2 stops18h 50m
Delta
Mon 20/418:34
MDW
-
MAN
2 stops13h 26m
Delta
Deal found 15/1£540
Tue 7/409:20
BRS
-
MDW
2 stops15h 20m
Delta
Tue 21/409:26
MDW
-
BRS
2 stops17h 24m
Delta
Deal found 14/1£697

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 16 January 2026.
Use the filters below to find and compare flights from Wales to Chicago Midway Airport that are best for you.

Fly from

Wales

Fly to

Midway

Route

Depart

Return

Price

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 18/2

13:00-22:31

1 stop15h 31m

Chicago Midway

Wed 25/2

13:49-10:10

2 stops14h 21m

£528

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Mon 2/3

17:15-17:37

2 stops30h 22m

Chicago Midway

Mon 9/3

13:10-09:50

2 stops15h 40m

£528

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 6/2

13:25-22:22

1 stop14h 57m

Chicago Midway

Wed 11/2

12:46-10:10

2 stops15h 24m

£531

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 9/3

20:40-18:40

2 stops27h 00m

Chicago Midway

Tue 17/3

17:40-10:30

1 stop11h 50m

£532

BristolChicago

BRS - MDW

BRSMDW

Bristol

Sat 28/2

06:00-16:14

2 stops16h 14m

Chicago Midway

Sat 7/3

13:29-13:10

2 stops17h 41m

£534

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 21/4

05:55-18:45

2 stops18h 50m

Chicago Midway

Sun 26/4

18:34-14:00

2 stops13h 26m

£540

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 1/2

05:50-17:55

2 stops18h 05m

Chicago Midway

Sun 8/2

13:26-10:10

2 stops14h 44m

£547

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 13/2

13:25-22:31

1 stop15h 06m

Chicago Midway

Wed 18/2

18:40-16:05

2 stops15h 25m

£548

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 23/4

13:00-22:29

1 stop15h 29m

Chicago Midway

Sat 2/5

13:10-10:20

2 stops15h 10m

£561

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 19/4

11:15-22:29

1 stop17h 14m

Chicago Midway

Sat 2/5

13:10-10:20

2 stops15h 10m

£577

Flights are sorted by cheapest return flights first.

Deals found on 15/1

Showing 1-10 of 22 results
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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 £531, Virgin Atlantic can have you in Chicago Midway Airport from Wales in 14h 57m. 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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Alternative routes for Wales to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Heathrow to O'Hare Intl flights
Gatwick to O'Hare Intl flights
Heathrow to Midway flights
London City to O'Hare Intl flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to Midway flights
Birmingham to O'Hare Intl flights
Gatwick to Midway flights
Birmingham to Midway flights
Glasgow Intl to O'Hare Intl flights
Inverness to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Glasgow Intl to Midway flights
Leeds to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Norwich to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Bristol to O'Hare Intl flights
Bristol to Midway flights
Southampton to O'Hare Intl flights
Southend to O'Hare Intl flights
Exeter to O'Hare Intl flights
London City to Midway flights
Newquay to O'Hare Intl flights
Leeds to Midway flights
Doncaster to O'Hare Intl flights
Southampton to Midway flights
Grimsby to O'Hare Intl flights
Darlington to Midway flights
Darlington to O'Hare Intl flights
Cardiff to Midway flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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?

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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.

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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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