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Cheap flights from Wales to Chicago Midway Airport from £293

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 22/10. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
3 Sep — 10 Sep1
1 adult

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 29 August 2025.

Round-trip from

£513

One-way from

£293
Virgin Atlantic
  • Virgin Atlantic
  • 1/10-6/10
  • 3 total stops
  • 30h 53m total
  • Wales to Chicago
Search Deals
22/10
  • 22/10
  • 3 total stops
  • 34h 30m 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 29 August 2025.

Wed 1/1011:55MAN - MDW
1 stop15h 41mVirgin Atlantic
Mon 6/1013:08MDW - MAN
2 stops15h 12mVirgin Atlantic
Deal found 28/8£513
Wed 1/1008:55MAN - MDW
2 stops15h 40mDelta
Mon 6/1018:23MDW - MAN
2 stops13h 02mDelta
Deal found 28/8£519
Fri 7/1113:25MAN - MDW
1 stop14h 49mVirgin Atlantic
Wed 12/1113:14MDW - MAN
2 stops14h 56mVirgin Atlantic
Deal found 27/8£525
Fri 7/1113:25MAN - MDW
1 stop14h 49mDelta
Wed 12/1113:47MDW - MAN
2 stops14h 23mDelta
Deal found 28/8£540
Wed 1/1006:15BRS - MDW
2 stops18h 20mDelta
Wed 8/1013:08MDW - BRS
2 stops13h 42mDelta
Deal found 27/8£546
Tue 23/912:35MAN - MDW
1 stop15h 01mDelta
Tue 7/1018:23MDW - MAN
2 stops13h 02mDelta
Deal found 27/8£548
Wed 24/905:55MAN - MDW
2 stops17h 40mDelta
Wed 8/1013:08MDW - MAN
2 stops12h 27mDelta
Deal found 27/8£552
Sun 12/1009:50CWL - MDW
2 stops38h 35mVirgin Atlantic
Sun 19/1013:08MDW - CWL
2 stops21h 37mVirgin Atlantic
Deal found 28/8£591
Sat 11/1006:15BRS - MDW
2 stops18h 10mDelta
Sat 18/1013:11MDW - BRS
2 stops13h 54mDelta
Deal found 27/8£619
Thu 16/1009:20BRS - MDW
2 stops15h 05mDelta
Fri 24/1009:20MDW - BRS
2 stops17h 30mDelta
Deal found 28/8£664
Sat 11/1009:45CWL - MDW
2 stops14h 40mDelta
Sat 18/1011:10MDW - CWL
2 stops16h 05mDelta
Deal found 27/8£699
Mon 6/1009:50CWL - MDW
2 stops14h 35mKLM
Mon 13/1013:08MDW - CWL
2 stops14h 07mKLM
Deal found 28/8£810

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 29 August 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

Wed 1/10

11:55-21:36

1 stop15h 41m

Chicago Midway

Mon 6/10

13:08-10:20

2 stops15h 12m

£513

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 1/10

08:55-18:35

2 stops15h 40m

Chicago Midway

Mon 6/10

18:23-13:25

2 stops13h 02m

£519

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 7/11

13:25-22:14

1 stop14h 49m

Chicago Midway

Wed 12/11

13:14-10:10

2 stops14h 56m

£525

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 19/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Tue 2/12

14:00-10:10

2 stops14h 10m

£540

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 7/11

13:25-22:14

1 stop14h 49m

Chicago Midway

Wed 12/11

13:47-10:10

2 stops14h 23m

£540

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 1/10

06:15-18:35

2 stops18h 20m

Chicago Midway

Wed 8/10

13:08-08:50

2 stops13h 42m

£546

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 23/9

12:35-21:36

1 stop15h 01m

Chicago Midway

Tue 7/10

18:23-13:25

2 stops13h 02m

£548

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Sun 12/10

09:50-18:25

2 stops38h 35m

Chicago Midway

Sun 19/10

13:08-16:45

2 stops21h 37m

£591

BristolChicago

BRS - MDW

BRSMDW

Bristol

Sat 11/10

06:15-18:25

2 stops18h 10m

Chicago Midway

Sat 18/10

13:11-09:05

2 stops13h 54m

£619

BristolChicago

BRS - MDW

BRSMDW

Bristol

Sun 12/10

06:15-18:25

2 stops18h 10m

Chicago Midway

Sun 19/10

09:35-08:50

2 stops17h 15m

£619

Flights are sorted by cheapest return flights first.

Deals found on 28/8

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 £810, Virgin Atlantic can have you in Chicago Midway Airport from Wales in 14h 35m. The distance between Wales and Chicago Midway Airport is about 3833 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
London City to O'Hare Intl flights
Heathrow to Midway flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Gatwick to Midway flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
Norwich to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Glasgow Intl to Midway flights
Birmingham to O'Hare Intl flights
Edinburgh to Midway flights
London City to Midway flights
Leeds to O'Hare Intl flights
Birmingham to Midway flights
Liverpool to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Bristol to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Bristol to Midway flights
Leeds to Midway flights
Exeter to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Southampton to O'Hare Intl flights
Cardiff to Midway flights
Newquay to O'Hare Intl flights
Southend to O'Hare Intl flights
Inverness to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Darlington to Midway flights
Darlington to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Southampton to Midway flights

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