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Cheap flights from Wales to Chicago Midway Airport from £246

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 15/1. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
27 Dec — 3 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 27 November 2025.

Round-trip from

£600

One-way from

£246
Virgin Atlantic
  • Virgin Atlantic
  • 27/2-2/3
  • 3 total stops
  • 35h 54m total
  • Wales to Chicago
Search Deals
15/1
  • 15/1
  • 3 total stops
  • 39h 49m 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 27 November 2025.

Mon 15/1213:00MAN - MDW
2 stops26h 54mDelta
Wed 7/118:14MDW - MAN
2 stops15h 51mDelta
Deal found 24/11£736
Mon 15/1213:00MAN - MDW
2 stops29h 34mDelta
Thu 8/113:28MDW - MAN
2 stops20h 37mDelta
Deal found 26/11£738
Mon 15/1213:00MAN - MDW
2 stops25h 54mDelta
Tue 6/113:28MDW - MAN
2 stops17h 17mDelta
Deal found 24/11£740
Wed 24/1205:50MAN - MDW
2 stops17h 36mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 24/11£742
Mon 29/1205:50MAN - MDW
2 stops17h 36mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 26/11£742
Wed 31/1213:30MAN - MDW
1 stop14h 52mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 26/11£745
Tue 16/1211:05MAN - MDW
2 stops18h 42mDelta
Tue 6/113:28MDW - MAN
2 stops17h 17mDelta
Deal found 25/11£751
Thu 25/1213:30MAN - MDW
1 stop14h 52mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 26/11£754
Wed 31/1213:30MAN - MDW
1 stop14h 52mDelta
Tue 6/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 25/11£761
Fri 28/1108:55BRS - MDW
2 stops15h 23mKLM
Tue 2/1213:14MDW - BRS
2 stops13h 11mKLM
Deal found 25/11£4,441
Fri 28/1108:55BRS - MDW
2 stops15h 23mDelta
Mon 1/1217:34MDW - BRS
2 stops17h 21mDelta
Deal found 25/11£4,512

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 27 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

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 4/2

10:20-08:52

2 stops28h 32m

Chicago Midway

Sun 8/2

17:00-16:55

2 stops41h 55m

£601

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 13/2

13:25-22:42

1 stop15h 17m

Chicago Midway

Wed 18/2

10:53-08:45

1 stop15h 52m

£604

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 21/1

06:00-17:55

2 stops17h 55m

Chicago Midway

Sun 25/1

19:16-10:15

2 stops32h 59m

£604

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

£642

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

£644

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 4/2

13:30-22:22

1 stop14h 52m

Chicago Midway

Sun 8/2

13:26-22:00

2 stops26h 34m

£646

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 16/1

13:25-22:07

1 stop14h 42m

Chicago Midway

Sun 25/1

13:26-10:10

2 stops14h 44m

£649

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 24/4

11:00-21:45

1 stop16h 45m

Chicago Midway

Fri 1/5

13:00-22:20

2 stops27h 20m

£655

BristolChicago

BRS - MDW

BRSMDW

Bristol

Fri 8/5

06:15-18:31

2 stops18h 16m

Chicago Midway

Tue 12/5

09:30-08:50

2 stops17h 20m

£715

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 7/5

09:20-18:31

2 stops15h 11m

Chicago Midway

Mon 11/5

17:59-17:00

2 stops17h 01m

£770

Flights are sorted by cheapest return flights first.

Deals found on 25/11

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 £604, Delta can have you in Chicago Midway Airport from Wales in 15h 17m. 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
London City to O'Hare Intl flights
Heathrow to Midway flights
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Gatwick to Midway flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to O'Hare Intl flights
Birmingham to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Edinburgh to Midway flights
Belfast Intl to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
London City to Midway flights
Glasgow Intl to Midway flights
Leeds to O'Hare Intl flights
Southend to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Leeds to Midway flights
Bristol to O'Hare Intl flights
Southampton to O'Hare Intl flights
Inverness to O'Hare Intl flights
Birmingham to Midway flights
Exeter to O'Hare Intl flights
Norwich to O'Hare Intl flights
Bristol to Midway flights
Cardiff to O'Hare Intl flights
Cardiff to Midway flights
Grimsby to O'Hare Intl flights
Darlington to Midway flights
Darlington to O'Hare Intl flights
Newquay to O'Hare Intl flights
Southampton to Midway flights
Doncaster 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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