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Cheap flights from Wales to Chicago Midway Airport from £358

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 30/8. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
14 Sep — 21 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 15 August 2026.

Mon 7/913:25 -
1 stop27h 35m
Wed 23/915:20 -
2 stops16h 40m
Deal found 14/8£611
Thu 24/909:20 -
2 stops14h 59m
Wed 30/919:01 -
2 stops15h 59m
Deal found 13/8£645
Thu 3/906:15 -
2 stops17h 46m
Tue 8/917:37 -
2 stops17h 23m
Deal found 12/8£656
Wed 16/905:55 -
2 stops18h 38m
Wed 23/919:13 -
2 stops15h 32m
Deal found 11/8£706
Sat 19/913:25 -
1 stop27h 35m
Sat 26/911:45 -
2 stops18h 30m
Deal found 13/8£709
Sun 22/1105:55 -
2 stops18h 09m
Sun 29/1109:30 -
2 stops18h 45m
Deal found 12/8£719
Fri 4/913:00 -
1 stop32h 44m
Thu 10/906:05 -
1 stop20h 45m
Deal found 15/8£733
Tue 29/905:55 -
2 stops18h 38m
Tue 6/1012:27 -
2 stops15h 33m
Deal found 15/8£735
Wed 16/908:55 -
2 stops15h 24m
Mon 21/913:19 -
2 stops14h 51m
Deal found 14/8£737
Wed 7/1005:55 -
2 stops18h 05m
Wed 14/1013:27 -
2 stops14h 43m
Deal found 13/8£738
Wed 16/905:55 -
2 stops18h 38m
Wed 23/913:19 -
2 stops14h 51m
Deal found 15/8£739
Sat 26/917:35 -
2 stops30h 44m
Sat 3/1013:19 -
2 stops21h 26m
Deal found 12/8£744

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 15 August 2026.

Round-trip from

£611

One-way from

£358
7/9-23/9
  • 7/9-23/9
  • 3 total stops
  • 44h 15m total
  • Wales to Chicago
Search Deals
30/8
  • 30/8
  • 3 total stops
  • 46h 50m 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 15 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

Thu 24/9

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

Thu 3/9

06:15-18:01

2 stops17h 46m

Chicago Midway

Tue 8/9

17:37-17:00

2 stops17h 23m

£656

BristolChicago

BRS Bristol - MDW Chicago Midway

BRSMDW

Bristol

Sun 22/11

05:55-18:04

2 stops18h 09m

Chicago Midway

Sun 29/11

09:30-10:15

2 stops18h 45m

£719

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Wed 16/9

08:55-18:19

2 stops15h 24m

Chicago Midway

Wed 23/9

19:01-16:45

2 stops15h 44m

£737

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

£746

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Mon 9/11

05:50-18:04

2 stops18h 14m

Chicago Midway

Sun 15/11

06:00-06:40

1 stop18h 40m

£759

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 17/9

05:55-18:33

2 stops18h 38m

Chicago Midway

Thu 24/9

09:29-08:25

2 stops16h 56m

£767

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 8/10

05:55-16:47

2 stops16h 52m

Chicago Midway

Sun 11/10

12:27-10:10

2 stops15h 43m

£798

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Wed 7/10

05:55-18:00

2 stops18h 05m

Chicago Midway

Sun 25/10

18:44-12:45

2 stops13h 01m

£818

BristolChicago

BRS Bristol - MDW Chicago Midway

BRSMDW

Bristol

Wed 16/12

05:55-16:39

2 stops16h 44m

Chicago Midway

Sun 27/12

09:30-16:55

2 stops25h 25m

£826

Flights are sorted by cheapest return flights first.

Deals found on 12/8

Showing 1-10 of 28 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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