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Cheap flights from Wales to Chicago Midway Airport from £322

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 17/1. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
9 Jan — 16 Jan1
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 10 December 2025.

Wed 24/1213:30MAN - MDW
1 stop14h 52mMultiple Airlines
Mon 29/1209:29MDW - MAN
2 stops18h 41mMultiple Airlines
Deal found 9/12£805
Wed 24/1205:50MAN - MDW
2 stops17h 36mDelta
Mon 29/1209:29MDW - MAN
2 stops16h 51mDelta
Deal found 9/12£810
Wed 24/1213:30MAN - MDW
1 stop14h 52mMultiple Airlines
Sun 28/1209:50MDW - MAN
2 stops16h 05mMultiple Airlines
Deal found 9/12£1,006
Wed 10/1213:30MAN - MDW
1 stop16h 17mKLM
Sun 14/1210:49MDW - MAN
2 stops15h 06mKLM
Deal found 8/12£1,032
Tue 23/1213:30MAN - MDW
1 stop25h 35mKLM
Tue 6/113:28MDW - MAN
2 stops14h 42mKLM
Deal found 9/12£1,245
Tue 16/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Sun 21/1209:29MDW - MAN
2 stops30h 01mVirgin Atlantic
Deal found 9/12£1,278
Sat 20/1213:30MAN - MDW
1 stop14h 52mKLM
Mon 29/1211:48MDW - MAN
2 stops14h 32mKLM
Deal found 9/12£1,347
Tue 16/1209:05MAN - MDW
2 stops14h 55mDelta
Sun 21/1217:05MDW - MAN
2 stops17h 30mDelta
Deal found 9/12£1,377
Sat 20/1213:30MAN - MDW
1 stop14h 52mMultiple Airlines
Tue 23/1217:05MDW - MAN
1 stop11h 25mMultiple Airlines
Deal found 9/12£1,404

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 10 December 2025.

Round-trip from

£564

One-way from

£322
Virgin Atlantic
  • Virgin Atlantic
  • 10/3-17/3
  • 3 total stops
  • 39h 32m total
  • Wales to Chicago
Search Deals
17/1
  • 17/1
  • 3 total stops
  • 34h 55m 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 10 December 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

Tue 3/2

13:30-22:22

1 stop14h 52m

Chicago Midway

Thu 19/2

13:26-10:10

2 stops14h 44m

£614

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 3/2

13:30-22:22

1 stop14h 52m

Chicago Midway

Tue 17/2

13:28-10:10

2 stops14h 42m

£614

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 2/2

09:00-17:29

1 stop14h 29m

Chicago Midway

Thu 19/2

13:26-10:10

2 stops14h 44m

£614

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 10/3

05:50-18:40

2 stops17h 50m

Chicago Midway

Tue 17/3

13:09-10:10

2 stops16h 01m

£615

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 3/2

13:30-22:22

1 stop14h 52m

Chicago Midway

Wed 18/2

12:46-08:45

1 stop13h 59m

£617

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 22/1

13:30-22:22

1 stop14h 52m

Chicago Midway

Thu 29/1

10:48-10:30

1 stop17h 42m

£619

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 2/2

05:50-22:22

2 stops22h 32m

Chicago Midway

Wed 18/2

09:34-08:45

2 stops17h 11m

£622

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 7/1

10:25-22:07

2 stops17h 42m

Chicago Midway

Wed 14/1

17:31-10:30

1 stop10h 59m

£624

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 22/1

06:00-17:55

2 stops17h 55m

Chicago Midway

Thu 29/1

13:26-10:15

2 stops14h 49m

£650

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 26/3

06:00-18:40

2 stops17h 40m

Chicago Midway

Thu 23/4

09:30-08:50

2 stops17h 20m

£834

Flights are sorted by cheapest return flights first.

Deals found on 7/12

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 £614, Delta 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
Heathrow to Midway flights
Gatwick to O'Hare Intl flights
London City to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Edinburgh to Midway flights
Gatwick to Midway flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Glasgow Intl to O'Hare Intl flights
Birmingham to O'Hare Intl flights
Glasgow Intl to Midway flights
Southampton to O'Hare Intl flights
Birmingham to Midway flights
Liverpool to O'Hare Intl flights
Leeds to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Inverness to O'Hare Intl flights
Southend to O'Hare Intl flights
Southampton to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
London City to Midway flights
Bristol to O'Hare Intl flights
Leeds to Midway flights
Newcastle upon Tyne to Midway flights
Grimsby to O'Hare Intl flights
Exeter to O'Hare Intl flights
Newquay to O'Hare Intl flights
Cardiff to Midway flights
Bristol to Midway flights
Cardiff to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Norwich to O'Hare Intl flights
Darlington to O'Hare Intl flights
Darlington to Midway flights

Fly with Cheapflights

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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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