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Cheap flights from Wales to Chicago Midway Airport from £306

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 18/2. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
27 Feb — 6 Mar1
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 January 2026.

Fri 20/213:25
MAN
-
MDW
1 stop15h 06m
KLM
Sun 22/213:28
MDW
-
MAN
2 stops12h 52m
KLM
Deal found 26/1£520
Thu 12/313:30
MAN
-
MDW
1 stop14h 01m
Virgin Atlantic
Mon 23/310:45
MDW
-
MAN
2 stops14h 45m
Virgin Atlantic
Deal found 27/1£521
Fri 6/213:25
MAN
-
MDW
1 stop14h 57m
Delta
Tue 10/213:26
MDW
-
MAN
2 stops14h 44m
Delta
Deal found 26/1£523
Thu 12/313:30
MAN
-
MDW
1 stop14h 01m
Virgin Atlantic
Thu 19/314:05
MDW
-
MAN
2 stops13h 15m
Virgin Atlantic
Deal found 25/1£523
Sun 1/205:50
MAN
-
MDW
2 stops18h 46m
Delta
Sun 8/213:26
MDW
-
MAN
2 stops14h 44m
Delta
Deal found 25/1£524
Fri 6/213:25
MAN
-
MDW
1 stop14h 57m
Delta
Wed 11/209:33
MDW
-
MAN
2 stops17h 12m
Delta
Deal found 26/1£526
Wed 11/317:25
CWL
-
MDW
2 stops28h 57m
KLM
Wed 18/313:10
MDW
-
CWL
2 stops15h 40m
KLM
Deal found 25/1£528
Fri 20/205:50
MAN
-
MDW
2 stops18h 50m
Delta
Sun 22/213:28
MDW
-
MAN
2 stops14h 42m
Delta
Deal found 26/1£529
Fri 6/313:25
MAN
-
MDW
1 stop15h 06m
Virgin Atlantic
Mon 9/313:10
MDW
-
MAN
2 stops13h 45m
Virgin Atlantic
Deal found 25/1£538
Wed 15/405:55
MAN
-
MDW
2 stops18h 03m
Delta
Sun 26/409:27
MDW
-
MAN
2 stops15h 48m
Delta
Deal found 27/1£539
Tue 29/913:00
MAN
-
MDW
1 stop14h 46m
Delta
Wed 14/1017:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 25/1£543
Thu 19/306:00
BRS
-
MDW
2 stops16h 54m
KLM
Mon 23/318:34
MDW
-
BRS
2 stops13h 36m
KLM
Deal found 26/1£546

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 January 2026.

Round-trip from

£520

One-way from

£306
KLM
  • KLM
  • 20/2-22/2
  • 3 total stops
  • 27h 58m total
  • Wales to Chicago
Search Deals
18/2
  • 18/2
  • 3 total stops
  • 49h 11m 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 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

Thu 12/3

13:30-22:31

1 stop14h 01m

Chicago Midway

Mon 23/3

10:45-06:30

2 stops14h 45m

£521

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 23/2

05:50-18:40

2 stops18h 50m

Chicago Midway

Mon 2/3

13:29-10:10

2 stops14h 41m

£524

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 6/3

05:50-18:40

2 stops18h 50m

Chicago Midway

Mon 9/3

14:05-10:10

2 stops15h 05m

£524

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 6/2

13:25-22:22

1 stop14h 57m

Chicago Midway

Wed 11/2

09:33-08:45

2 stops17h 12m

£526

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 11/3

17:25-17:22

2 stops28h 57m

Chicago Midway

Wed 18/3

13:10-09:50

2 stops15h 40m

£528

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 15/4

10:50-22:28

1 stop17h 38m

Chicago Midway

Sun 26/4

09:27-07:15

2 stops15h 48m

£538

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 19/3

06:00-17:54

2 stops16h 54m

Chicago Midway

Mon 23/3

18:34-13:10

2 stops13h 36m

£546

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 18/3

06:00-17:54

2 stops16h 54m

Chicago Midway

Tue 24/3

18:34-13:10

2 stops13h 36m

£558

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 19/3

06:00-17:54

2 stops16h 54m

Chicago Midway

Tue 24/3

13:10-13:10

2 stops19h 00m

£558

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 12/3

05:50-17:54

2 stops17h 04m

Chicago Midway

Thu 19/3

09:35-07:55

2 stops17h 20m

£560

Flights are sorted by cheapest return flights first.

Deals found on 26/1

Showing 1-10 of 31 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 £521, Virgin Atlantic can have you in Chicago Midway Airport from Wales in 14h 01m. 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
Heathrow to Midway flights
Gatwick to O'Hare Intl flights
London City to O'Hare Intl flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Manchester to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Manchester to Midway flights
Gatwick to Midway flights
Edinburgh to Midway flights
Birmingham to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
Birmingham to Midway flights
Glasgow Intl to Midway flights
Norwich to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Inverness to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Bristol to O'Hare Intl flights
Leeds to O'Hare Intl flights
Bristol to Midway flights
Belfast Intl to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Newquay to O'Hare Intl flights
Southend to O'Hare Intl flights
Southampton to O'Hare Intl flights
London City to Midway flights
Exeter to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Leeds to Midway flights
Darlington to Midway flights
Darlington to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Southampton to Midway flights
Cardiff to Midway flights

Fly with Cheapflights

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How does Cheapflights help users find flights 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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