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Cheap flights from Wales to Chicago Midway Airport from £360

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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 17 September 2025.

Round-trip from

£491

One-way from

£360
Virgin Atlantic
  • Virgin Atlantic
  • 5/11-9/11
  • 2 total stops
  • 28h 27m total
  • Wales to Chicago
Search Deals
1/10
  • 1/10
  • 3 total stops
  • 48h 48m total
  • Wales to Chicago
Search Deals

Find flight deals from Wales to Midway

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 17 September 2025.

Fri 28/1113:25MAN - MDW
1 stop16h 07mVirgin Atlantic
Wed 3/1209:34MDW - MAN
2 stops16h 46mVirgin Atlantic
Deal found 16/9£494
Tue 23/912:35MAN - MDW
1 stop15h 01mVirgin Atlantic
Tue 7/1012:48MDW - MAN
1 stop13h 47mVirgin Atlantic
Deal found 15/9£496
Thu 25/912:35MAN - MDW
1 stop15h 01mMultiple Airlines
Tue 30/910:35MDW - MAN
1 stop16h 00mMultiple Airlines
Deal found 14/9£499
Thu 2/1012:35MAN - MDW
1 stop15h 01mVirgin Atlantic
Mon 13/1010:35MDW - MAN
1 stop16h 00mVirgin Atlantic
Deal found 14/9£500
Thu 20/1113:30MAN - MDW
1 stop16h 02mDelta
Sat 6/1213:14MDW - MAN
2 stops14h 56mDelta
Deal found 15/9£508
Thu 6/1109:05MAN - MDW
2 stops15h 20mDelta
Fri 14/1113:14MDW - MAN
2 stops14h 56mDelta
Deal found 16/9£510
Thu 20/1113:30MAN - MDW
1 stop16h 02mDelta
Sat 29/1113:47MDW - MAN
2 stops16h 58mDelta
Deal found 15/9£513
Wed 29/1008:55BRS - MDW
2 stops18h 19mVirgin Atlantic
Wed 5/1113:08MDW - BRS
2 stops13h 17mVirgin Atlantic
Deal found 14/9£513
Wed 5/1120:40MAN - MDW
2 stops25h 34mVirgin Atlantic
Tue 11/1113:47MDW - MAN
2 stops14h 23mVirgin Atlantic
Deal found 15/9£513
Tue 23/912:35MAN - MDW
1 stop15h 01mDelta
Tue 7/1018:23MDW - MAN
2 stops16h 32mDelta
Deal found 14/9£516
Sun 5/1014:15MAN - MDW
2 stops31h 54mDelta
Mon 17/1113:47MDW - MAN
2 stops14h 23mDelta
Deal found 16/9£517
Mon 6/1009:50CWL - MDW
2 stops36h 19mMultiple Airlines
Mon 13/1013:08MDW - CWL
2 stops14h 07mMultiple Airlines
Deal found 16/9£568

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 17 September 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 20/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Sat 6/12

13:14-10:10

2 stops14h 56m

£508

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 20/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Sat 6/12

13:14-10:10

2 stops14h 56m

£508

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 5/11

13:30-22:14

1 stop14h 44m

Chicago Midway

Tue 11/11

13:47-10:10

2 stops14h 23m

£508

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 6/11

09:05-18:25

2 stops15h 20m

Chicago Midway

Fri 14/11

13:14-10:10

2 stops14h 56m

£510

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 20/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Sat 29/11

13:47-12:45

2 stops16h 58m

£513

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sat 8/11

13:30-22:14

1 stop14h 44m

Chicago Midway

Mon 24/11

13:14-08:20

2 stops13h 06m

£513

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 19/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Mon 24/11

13:14-08:20

2 stops13h 06m

£513

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 30/10

13:30-08:40

2 stops24h 10m

Chicago Midway

Thu 6/11

09:35-10:10

2 stops18h 35m

£516

BristolChicago

BRS - MDW

BRSMDW

Bristol

Fri 31/10

08:55-22:14

2 stops18h 19m

Chicago Midway

Fri 7/11

10:40-08:25

2 stops15h 45m

£532

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 5/3

10:20-08:50

2 stops28h 30m

Chicago Midway

Mon 9/3

13:00-16:55

2 stops22h 55m

£545

Flights are sorted by cheapest return flights first.

Deals found on 14/9

Showing 1-10 of 24 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 £508, Delta can have you in Chicago Midway Airport from Wales in 16h 02m. 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 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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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
Luton to O'Hare Intl flights
Stansted to O'Hare Intl flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Gatwick to Midway flights
Edinburgh to O'Hare Intl flights
Birmingham to O'Hare Intl flights
Edinburgh to Midway flights
London City to Midway flights
Birmingham to Midway flights
Leeds to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Belfast Intl to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Leeds to Midway flights
Glasgow Intl to Midway flights
Inverness to O'Hare Intl flights
Darlington to O'Hare Intl flights
Cardiff to Midway flights
Southampton to O'Hare Intl flights
Southend to O'Hare Intl flights
Norwich to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Darlington to Midway flights
Exeter to O'Hare Intl flights
Bristol to O'Hare Intl flights
Southampton to Midway flights
Bristol to Midway flights
Doncaster to O'Hare Intl flights
Newquay to O'Hare Intl flights

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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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