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Cheap flights from Wales to Chicago Midway Airport from £305

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 15/12. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
25 Dec — 1 Jan1
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 25 November 2025.

Round-trip from

£605

One-way from

£305
Virgin Atlantic
  • Virgin Atlantic
  • 27/2-2/3
  • 3 total stops
  • 35h 54m total
  • Wales to Chicago
Search Deals
15/12
  • 15/12
  • 3 total stops
  • 36h 51m 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 25 November 2025.

Mon 15/1213:00MAN - MDW
2 stops26h 54mDelta
Wed 7/118:14MDW - MAN
2 stops15h 51mDelta
Deal found 24/11£741
Mon 15/1205:50MAN - MDW
2 stops18h 10mDelta
Thu 8/109:32MDW - MAN
2 stops18h 38mDelta
Deal found 23/11£743
Wed 24/1205:50MAN - MDW
2 stops17h 36mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 24/11£747
Thu 25/1213:30MAN - MDW
1 stop25h 35mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 24/11£776
Fri 26/1205:50MAN - MDW
2 stops17h 36mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 24/11£777
Tue 16/1209:05MAN - MDW
2 stops20h 42mDelta
Tue 6/113:28MDW - MAN
2 stops17h 17mDelta
Deal found 24/11£798
Wed 17/1213:40MAN - MDW
2 stops16h 07mDelta
Wed 7/111:21MDW - MAN
1 stop17h 09mDelta
Deal found 23/11£821
Fri 26/1213:25MAN - MDW
1 stop14h 57mDelta
Tue 6/111:21MDW - MAN
1 stop17h 09mDelta
Deal found 24/11£823

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 25 November 2025.
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 5/2

13:30-22:22

1 stop14h 52m

Chicago Midway

Mon 9/2

13:26-10:10

2 stops14h 44m

£614

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 5/2

13:30-22:22

1 stop14h 52m

Chicago Midway

Mon 9/2

13:26-10:10

2 stops14h 44m

£644

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 4/2

10:20-12:46

2 stops32h 26m

Chicago Midway

Sun 8/2

17:00-16:55

2 stops41h 55m

£646

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 13/2

13:25-22:42

1 stop15h 17m

Chicago Midway

Wed 18/2

09:34-08:45

2 stops17h 11m

£647

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 4/2

13:00-12:46

2 stops29h 46m

Chicago Midway

Sun 8/2

13:26-12:45

2 stops17h 19m

£649

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 21/1

06:00-17:55

2 stops17h 55m

Chicago Midway

Sun 25/1

13:49-10:15

2 stops38h 26m

£650

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 12/1

05:50-16:29

2 stops16h 39m

Chicago Midway

Mon 19/1

09:32-06:30

2 stops14h 58m

£656

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 8/2

19:40-17:29

2 stops27h 49m

Chicago Midway

Sun 15/2

09:34-08:20

2 stops16h 46m

£658

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sat 7/3

13:30-22:42

1 stop15h 12m

Chicago Midway

Sun 15/3

13:09-10:10

2 stops16h 01m

£675

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 1/2

05:50-17:55

2 stops18h 05m

Chicago Midway

Sun 8/2

09:33-10:10

2 stops18h 37m

£676

Flights are sorted by cheapest return flights first.

Deals found on 23/11

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 £614, Virgin Atlantic can have you in Chicago Midway Airport from Wales in 14h 52m. 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
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Heathrow to Midway flights
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Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to O'Hare Intl flights
Edinburgh to Midway flights
Birmingham to O'Hare Intl flights
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Southampton to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Bristol to Midway flights
Leeds to Midway flights
Belfast City to O'Hare Intl flights
Southend to O'Hare Intl flights
Glasgow Intl to Midway flights
Leeds to O'Hare Intl flights
Southampton to Midway flights
Birmingham to Midway flights
London City to Midway flights
Bristol to O'Hare Intl flights
Exeter to O'Hare Intl flights
Darlington to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Cardiff to O'Hare Intl flights
Norwich to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Darlington to Midway flights
Cardiff to Midway flights
Doncaster to O'Hare Intl flights
Newquay to O'Hare Intl flights
Inverness to O'Hare Intl flights

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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.

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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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