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Cheap flights from Wales to Chicago Midway Airport from £359

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 24/12. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
14 Dec — 21 Dec1
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 14 November 2025.

Round-trip from

£597

One-way from

£359
Virgin Atlantic
  • Virgin Atlantic
  • 8/1-22/1
  • 2 total stops
  • 32h 16m total
  • Wales to Chicago
Search Deals
24/12
  • 24/12
  • 3 total stops
  • 54h 20m 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 14 November 2025.

Sun 7/1209:05MAN - MDW
1 stop13h 13mDelta
Wed 21/113:28MDW - MAN
2 stops14h 42mDelta
Deal found 13/11£676
Fri 28/1113:25MAN - MDW
1 stop16h 15mDelta
Tue 2/1213:14MDW - MAN
2 stops14h 56mDelta
Deal found 11/11£678
Sat 6/1205:50MAN - MDW
2 stops18h 28mDelta
Mon 8/1213:14MDW - MAN
2 stops14h 56mDelta
Deal found 11/11£679
Tue 2/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Sun 14/1209:34MDW - MAN
2 stops29h 56mVirgin Atlantic
Deal found 13/11£683
Thu 11/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Sun 14/1209:34MDW - MAN
2 stops29h 56mVirgin Atlantic
Deal found 12/11£694
Thu 4/1213:30MAN - MDW
1 stop16h 17mDelta
Sun 7/1206:00MDW - MAN
1 stop18h 30mDelta
Deal found 11/11£711
Tue 2/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Sun 7/1210:49MDW - MAN
1 stop13h 41mVirgin Atlantic
Deal found 13/11£730
Fri 28/1113:25MAN - MDW
1 stop16h 15mVirgin Atlantic
Tue 2/1210:49MDW - MAN
1 stop17h 41mVirgin Atlantic
Deal found 11/11£732
Tue 25/1113:30MAN - MDW
1 stop16h 10mVirgin Atlantic
Tue 2/1210:49MDW - MAN
1 stop17h 41mVirgin Atlantic
Deal found 12/11£762
Thu 27/1106:00BRS - MDW
2 stops16h 39mKLM
Sun 7/1213:14MDW - BRS
2 stops13h 11mKLM
Deal found 13/11£811
Sun 28/1206:00BRS - MDW
2 stops16h 20mMultiple Airlines
Sun 4/109:29MDW - BRS
2 stops30h 41mMultiple Airlines
Deal found 12/11£1,113

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 14 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

Fri 13/2

13:25-22:44

1 stop15h 19m

Chicago Midway

Wed 18/2

12:46-08:45

1 stop13h 59m

£597

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 8/1

13:30-22:09

1 stop14h 39m

Chicago Midway

Thu 22/1

13:28-10:10

2 stops14h 42m

£622

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 13/1

13:30-22:09

1 stop14h 39m

Chicago Midway

Sun 18/1

06:45-08:40

1 stop19h 55m

£637

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 13/1

05:50-16:31

2 stops16h 41m

Chicago Midway

Sun 18/1

13:28-08:20

2 stops12h 52m

£641

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 13/1

13:30-22:09

1 stop14h 39m

Chicago Midway

Sun 18/1

13:49-10:10

2 stops14h 21m

£643

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 13/2

13:25-22:44

1 stop15h 19m

Chicago Midway

Wed 18/2

09:34-08:45

2 stops17h 11m

£646

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 5/3

13:30-22:44

1 stop15h 14m

Chicago Midway

Mon 9/3

17:59-06:40

2 stops31h 41m

£646

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 4/3

08:55-09:08

2 stops30h 13m

Chicago Midway

Sun 8/3

18:45-08:25

2 stops32h 40m

£669

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 27/11

06:00-16:39

2 stops16h 39m

Chicago Midway

Sun 7/12

13:14-08:25

2 stops13h 11m

£811

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 26/3

10:20-08:50

2 stops27h 30m

Chicago Midway

Mon 30/3

17:59-09:15

2 stops33h 16m

£880

Flights are sorted by cheapest return flights first.

Deals found on 13/11

Showing 1-10 of 21 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 £597, Virgin Atlantic can have you in Chicago Midway Airport from Wales in 15h 19m. 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
Gatwick to Midway flights
Manchester to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Manchester to Midway flights
Glasgow Intl to O'Hare Intl flights
Bristol to O'Hare Intl flights
Bristol to Midway flights
Birmingham to O'Hare Intl flights
Edinburgh to Midway flights
Southend to O'Hare Intl flights
Birmingham to Midway flights
London City to Midway flights
Belfast Intl to O'Hare Intl flights
Leeds to O'Hare Intl flights
Glasgow Intl to Midway flights
Belfast City to O'Hare Intl flights
Leeds to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
Southampton to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Darlington to Midway flights
Southampton to Midway flights
Norwich to O'Hare Intl flights
Newquay to O'Hare Intl flights
Darlington to O'Hare Intl flights
Exeter to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Inverness to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Cardiff to Midway flights

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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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