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Cheap flights from Wales to Chicago Midway Airport from £224

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 14/1. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
2 Jan — 9 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 3 December 2025.

Tue 30/1213:30MAN - MDW
1 stop14h 52mKLM
Thu 29/113:26MDW - MAN
2 stops12h 54mKLM
Deal found 1/12£726
Tue 16/1205:50MAN - MDW
2 stops18h 10mMultiple Airlines
Sun 21/1209:50MDW - MAN
2 stops40h 05mMultiple Airlines
Deal found 1/12£775
Tue 16/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Sun 21/1209:50MDW - MAN
2 stops40h 05mVirgin Atlantic
Deal found 1/12£775
Thu 11/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Fri 16/106:45MDW - MAN
1 stop21h 45mVirgin Atlantic
Deal found 1/12£864
Tue 30/1213:30MAN - MDW
1 stop14h 52mDelta
Thu 29/112:48MDW - MAN
1 stop15h 42mDelta
Deal found 1/12£865
Tue 30/1205:50MAN - MDW
2 stops22h 32mVirgin Atlantic
Thu 29/113:26MDW - MAN
2 stops15h 04mVirgin Atlantic
Deal found 1/12£903
Thu 11/1213:30MAN - MDW
1 stop16h 17mMultiple Airlines
Fri 16/113:49MDW - MAN
2 stops14h 21mMultiple Airlines
Deal found 1/12£911
Tue 16/1205:50MAN - MDW
2 stops18h 10mDelta
Sun 21/1209:29MDW - MAN
2 stops16h 51mDelta
Deal found 2/12£1,504
Wed 24/1213:30MAN - MDW
1 stop14h 52mVirgin Atlantic
Wed 7/117:31MDW - MAN
1 stop10h 59mVirgin Atlantic
Deal found 1/12£3,797
Wed 24/1213:30MAN - MDW
1 stop25h 35mMultiple Airlines
Wed 7/118:14MDW - MAN
2 stops15h 51mMultiple Airlines
Deal found 1/12£4,518

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 3 December 2025.

Round-trip from

£573

One-way from

£224
KLM
  • KLM
  • 16/1-23/1
  • 4 total stops
  • 43h 25m total
  • Wales to Chicago
Search Deals
14/1
  • 14/1
  • 3 total stops
  • 55h 44m 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 3 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

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Fri 16/1

17:15-16:16

2 stops29h 01m

Chicago Midway

Fri 23/1

13:26-09:50

2 stops14h 24m

£573

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 14/1

17:25-17:34

2 stops30h 09m

Chicago Midway

Wed 21/1

13:29-09:50

2 stops14h 21m

£574

BristolChicago

BRS - MDW

BRSMDW

Bristol

Thu 15/1

06:00-17:34

2 stops17h 34m

Chicago Midway

Fri 23/1

13:26-09:55

2 stops14h 29m

£578

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 4/2

10:20-18:36

2 stops38h 16m

Chicago Midway

Sun 8/2

13:26-16:45

2 stops21h 19m

£603

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 21/1

06:00-18:36

2 stops18h 36m

Chicago Midway

Sun 25/1

09:32-10:15

2 stops18h 43m

£608

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 20/1

13:30-12:49

2 stops29h 19m

Chicago Midway

Mon 9/2

13:51-10:10

2 stops14h 19m

£615

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 21/1

13:00-08:52

2 stops25h 52m

Chicago Midway

Mon 9/2

13:51-10:10

2 stops14h 19m

£615

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 20/1

13:30-09:53

1 stop26h 23m

Chicago Midway

Tue 10/2

18:35-16:05

2 stops15h 30m

£615

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 19/1

09:05-08:52

2 stops29h 47m

Chicago Midway

Mon 9/2

13:26-10:10

2 stops14h 44m

£616

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 19/1

09:05-08:52

2 stops29h 47m

Chicago Midway

Tue 10/2

18:35-18:40

2 stops18h 05m

£616

Flights are sorted by cheapest return flights first.

Deals found on 2/12

Showing 1-10 of 25 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 £573, KLM can have you in Chicago Midway Airport from Wales in 29h 01m. 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
Heathrow to Midway flights
Gatwick to O'Hare Intl flights
London City to O'Hare Intl flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Gatwick to Midway flights
Manchester to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Birmingham to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
Birmingham to Midway flights
Glasgow Intl to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Glasgow Intl to Midway flights
Southend to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
London City to Midway flights
Inverness to O'Hare Intl flights
Leeds to O'Hare Intl flights
Leeds to Midway flights
Belfast City to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Bristol to O'Hare Intl flights
Southampton to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Cardiff to Midway flights
Southampton to Midway flights
Bristol to Midway flights
Darlington to Midway flights
Darlington to O'Hare Intl flights
Exeter to O'Hare Intl flights
Newquay to O'Hare Intl flights
Norwich to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Doncaster to O'Hare Intl 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.

Why should you use Cheapflights to find cheap flight tickets 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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