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Cheap flights from Wales to Chicago Midway Airport from £372

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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
7 Sep — 14 Sep1
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 8 August 2026.

Fri 25/913:25 -
1 stop27h 35m
Fri 9/1015:20 -
2 stops24h 05m
Deal found 4/8£596
Wed 23/909:20 -
2 stops14h 59m
Wed 30/919:01 -
2 stops15h 59m
Deal found 7/8£645
Wed 23/906:15 -
2 stops18h 18m
Wed 30/914:00 -
2 stops21h 00m
Deal found 5/8£655
Tue 1/909:20 -
2 stops14h 41m
Tue 29/913:19 -
2 stops13h 31m
Deal found 4/8£656
Tue 10/1112:40 -
1 stop16h 16m
Tue 17/1113:22 -
2 stops14h 43m
Deal found 5/8£697
Thu 10/909:45 -
2 stops18h 59m
Wed 16/919:01 -
2 stops15h 44m
Deal found 8/8£698
Mon 7/920:50 -
2 stops26h 07m
Mon 5/1013:19 -
2 stops13h 06m
Deal found 5/8£705
Thu 10/909:45 -
2 stops18h 59m
Wed 16/919:01 -
2 stops15h 44m
Deal found 7/8£705
Wed 16/905:55 -
2 stops18h 38m
Wed 23/919:13 -
2 stops15h 32m
Deal found 6/8£706
Mon 28/905:55 -
2 stops18h 38m
Tue 6/1013:27 -
2 stops12h 58m
Deal found 8/8£707
Tue 6/1013:00 -
1 stop15h 33m
Tue 20/1012:45 -
1 stop14h 05m
Deal found 7/8£713
Wed 7/1012:10 -
2 stops16h 23m
Wed 14/1013:27 -
2 stops12h 58m
Deal found 5/8£714

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 8 August 2026.

Round-trip from

£596

One-way from

£372
25/9-9/10
  • 25/9-9/10
  • 3 total stops
  • 51h 40m total
  • Wales to Chicago
Search Deals
5/9
  • 5/9
  • 2 total stops
  • 37h 45m 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 8 August 2026.
Use the filters below to find and compare flights from Wales to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

BristolChicago

BRS Bristol - MDW Chicago Midway

BRSMDW

Bristol

Wed 23/9

09:20-18:19

2 stops14h 59m

Chicago Midway

Wed 30/9

19:01-17:00

2 stops15h 59m

£645

BristolChicago

BRS Bristol - MDW Chicago Midway

BRSMDW

Bristol

Wed 23/9

06:15-18:33

2 stops18h 18m

Chicago Midway

Wed 30/9

14:00-17:00

2 stops21h 00m

£655

BristolChicago

BRS Bristol - MDW Chicago Midway

BRSMDW

Bristol

Tue 1/9

06:15-16:59

2 stops16h 44m

Chicago Midway

Tue 29/9

09:59-08:50

2 stops16h 51m

£656
Fastest return journey

BristolChicago

BRS Bristol - MDW Chicago Midway

BRSMDW

Bristol

Tue 1/9

09:20-18:01

2 stops14h 41m

Chicago Midway

Tue 29/9

13:19-08:50

2 stops13h 31m

£656

CardiffChicago

CWL Cardiff Wales - MDW Chicago Midway

CWLMDW

Cardiff Wales

Thu 10/9

09:45-22:44

2 stops18h 59m

Chicago Midway

Wed 16/9

19:01-16:45

2 stops15h 44m

£698

CardiffChicago

CWL Cardiff Wales - MDW Chicago Midway

CWLMDW

Cardiff Wales

Thu 10/9

09:45-22:44

2 stops18h 59m

Chicago Midway

Wed 16/9

19:01-16:45

2 stops15h 44m

£705

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Mon 5/10

08:55-18:19

2 stops15h 24m

Chicago Midway

Sun 18/10

13:27-10:10

2 stops14h 43m

£768

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 17/9

05:55-18:33

2 stops18h 38m

Chicago Midway

Wed 30/9

13:19-08:25

2 stops13h 06m

£768

BristolChicago

BRS Bristol - MDW Chicago Midway

BRSMDW

Bristol

Mon 31/8

17:30-15:44

2 stops28h 14m

Chicago Midway

Mon 7/9

19:25-17:00

2 stops15h 35m

£791

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Fri 25/9

05:55-18:19

2 stops18h 24m

Chicago Midway

Fri 9/10

13:27-10:10

2 stops14h 43m

£797

Flights are sorted by cheapest return flights first.

Deals found on 7/8

Showing 1-10 of 22 resultsSorted by cheapest first
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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 £645, KLM can have you in Chicago Midway Airport from Wales in 14h 59m. The distance between Wales and Chicago Midway Airport is about 3858 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 Cardiff Wales - Chicago Midway or Bristol - 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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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?

Millions of users choose and trust Cheapflights to book the best flight deals from Wales to Midway for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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.

Can Cheapflights notify me if prices for flights from Wales to Midway become cheaper?

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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