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Cheap flights from Wales to Chicago Midway Airport from £423

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 19/12. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
30 Nov — 7 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 31 October 2025.

Round-trip from

£619

One-way from

£423
Delta
  • Delta
  • 4/2-9/2
  • 3 total stops
  • 29h 38m total
  • Wales to Chicago
Search Deals
19/12
  • 19/12
  • 2 total stops
  • 44h 25m 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 31 October 2025.

Wed 3/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Sun 7/1212:50MDW - MAN
1 stop11h 40mVirgin Atlantic
Deal found 29/10£626
Wed 19/1113:30MAN - MDW
1 stop16h 10mVirgin Atlantic
Tue 25/1113:15MDW - MAN
2 stops26h 15mVirgin Atlantic
Deal found 29/10£631
Thu 27/1110:20CWL - MDW
2 stops19h 20mKLM
Thu 4/1213:14MDW - CWL
2 stops14h 36mKLM
Deal found 30/10£636
Thu 27/1113:30MAN - MDW
1 stop16h 10mDelta
Mon 1/1213:15MDW - MAN
2 stops14h 55mDelta
Deal found 30/10£640
Wed 3/1213:30MAN - MDW
1 stop16h 17mMultiple Airlines
Sun 7/1217:13MDW - MAN
2 stops33h 07mMultiple Airlines
Deal found 29/10£642
Thu 27/1113:30MAN - MDW
1 stop16h 10mDelta
Thu 4/1213:14MDW - MAN
2 stops14h 56mDelta
Deal found 29/10£648
Wed 19/1113:00MAN - MDW
2 stops16h 40mDelta
Mon 24/1113:15MDW - MAN
2 stops17h 30mDelta
Deal found 29/10£658
Fri 28/1113:25MAN - MDW
1 stop16h 15mDelta
Fri 5/1213:14MDW - MAN
2 stops14h 56mDelta
Deal found 31/10£668
Thu 4/1206:00BRS - MDW
2 stops18h 18mKLM
Mon 8/1209:34MDW - BRS
2 stops16h 51mKLM
Deal found 29/10£678
Thu 13/1108:55BRS - MDW
2 stops15h 13mDelta
Sun 16/1109:34MDW - BRS
2 stops16h 51mDelta
Deal found 30/10£753
Fri 28/1110:20CWL - MDW
2 stops19h 20mMultiple Airlines
Fri 5/1213:14MDW - CWL
2 stops14h 36mMultiple Airlines
Deal found 29/10£814
Sun 14/1213:40BRS - MDW
2 stops16h 07mMultiple Airlines
Sun 21/1209:29MDW - BRS
2 stops21h 41mMultiple Airlines
Deal found 29/10£999

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 31 October 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 4/2

13:30-22:26

1 stop14h 56m

Chicago Midway

Mon 9/2

13:28-10:10

2 stops14h 42m

£619

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 18/3

05:50-18:08

2 stops17h 18m

Chicago Midway

Mon 23/3

13:00-10:10

2 stops16h 10m

£621

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 15/4

11:00-09:51

1 stop28h 51m

Chicago Midway

Mon 27/4

17:59-14:00

2 stops14h 01m

£631

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 19/11

13:30-23:40

1 stop16h 10m

Chicago Midway

Tue 25/11

10:47-10:30

1 stop17h 43m

£634

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 27/11

10:20-23:40

2 stops19h 20m

Chicago Midway

Thu 4/12

13:14-09:50

2 stops14h 36m

£636

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 21/1

06:00-17:55

2 stops17h 55m

Chicago Midway

Sat 31/1

13:28-09:55

2 stops14h 27m

£641

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 3/12

13:30-23:47

1 stop16h 17m

Chicago Midway

Sun 7/12

17:13-08:20

2 stops33h 07m

£642

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 13/2

13:25-21:46

1 stop14h 21m

Chicago Midway

Wed 18/2

14:00-10:10

2 stops14h 10m

£646

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 27/11

11:00-23:40

2 stops18h 40m

Chicago Midway

Mon 1/12

13:15-10:10

2 stops14h 55m

£646

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 5/3

13:30-21:46

1 stop14h 16m

Chicago Midway

Mon 9/3

13:00-06:40

2 stops36h 40m

£647

Flights are sorted by cheapest return flights first.

Deals found on 29/10

Showing 1-10 of 34 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 £619, Delta can have you in Chicago Midway Airport from Wales in 14h 56m. 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
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Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to O'Hare Intl flights
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Southend to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
Edinburgh to Midway flights
London City to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
Glasgow Intl to Midway flights
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Leeds to Midway flights
Belfast City to O'Hare Intl flights
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Birmingham to Midway flights
Newcastle upon Tyne to Midway flights
Bristol to Midway flights
Inverness to O'Hare Intl flights
Cardiff to Midway flights
Liverpool to O'Hare Intl flights
Exeter to O'Hare Intl flights
Darlington to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Southampton to Midway flights
Grimsby to O'Hare Intl flights
Darlington to Midway flights
Newquay to O'Hare Intl flights
Norwich to O'Hare Intl flights
Doncaster to O'Hare Intl 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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