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Cheap flights from Wales to Chicago Midway Airport from £313

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 7/6. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — MDW
15 Jun — 22 Jun1
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 16 May 2026.

Thu 4/611:35
CWL
-
MDW
1 stop28h 00m
Multiple Airlines
Sat 13/618:35
MDW
-
CWL
2 stops33h 40m
Multiple Airlines
Deal found 12/5£722
Sun 14/620:55
MAN
-
MDW
2 stops42h 40m
Multiple Airlines
Sat 27/610:25
MDW
-
MAN
1 stop19h 15m
Multiple Airlines
Deal found 12/5£727
Wed 16/905:55
MAN
-
MDW
2 stops18h 10m
Delta
Wed 23/913:05
MDW
-
MAN
1 stop12h 10m
Delta
Deal found 16/5£730
Wed 23/910:40
MAN
-
MDW
1 stop17h 06m
Delta
Wed 30/913:05
MDW
-
MAN
1 stop12h 10m
Delta
Deal found 15/5£736
Fri 19/620:55
MAN
-
MDW
2 stops42h 45m
Multiple Airlines
Fri 3/715:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 12/5£747
Thu 10/1213:30
MAN
-
MDW
1 stop14h 15m
Virgin Atlantic
Tue 15/1217:25
MDW
-
MAN
1 stop11h 05m
Virgin Atlantic
Deal found 15/5£752
Mon 5/1005:55
MAN
-
MDW
2 stops18h 36m
Delta
Sun 18/1009:30
MDW
-
MAN
2 stops15h 45m
Delta
Deal found 16/5£760
Fri 9/1013:00
MAN
-
MDW
1 stop14h 45m
Delta
Wed 14/1009:30
MDW
-
MAN
2 stops16h 55m
Delta
Deal found 16/5£760
Mon 15/606:15
BRS
-
MDW
2 stops18h 03m
Delta
Mon 22/618:58
MDW
-
BRS
2 stops16h 02m
Delta
Deal found 16/5£768
Sat 20/606:15
BRS
-
MDW
2 stops22h 02m
KLM
Sun 28/618:58
MDW
-
BRS
2 stops21h 07m
KLM
Deal found 16/5£774
Mon 8/606:15
BRS
-
MDW
2 stops18h 03m
Delta
Mon 15/613:26
MDW
-
BRS
2 stops17h 49m
Delta
Deal found 14/5£778
Mon 8/622:10
CWL
-
MDW
3 stops44h 36m
Multiple Airlines
Mon 15/609:17
MDW
-
CWL
2 stops18h 58m
Multiple Airlines
Deal found 12/5£784

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 16 May 2026.

Round-trip from

£722

One-way from

£328
WestJet
  • WestJet
  • 4/6-13/6
  • 3 total stops
  • 61h 40m total
  • Wales to Chicago
Search Deals
16/6
  • 16/6
  • 3 total stops
  • 31h 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 16 May 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

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Wed 23/9

13:05-07:15

1 stop12h 10m

£736
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 11/9

13:00-21:46

1 stop14h 46m

Chicago Midway

Wed 16/9

13:05-07:15

1 stop12h 10m

£767

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 15/6

06:15-18:18

2 stops18h 03m

Chicago Midway

Mon 22/6

18:58-17:00

2 stops16h 02m

£768

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 16/6

06:15-18:18

2 stops18h 03m

Chicago Midway

Thu 25/6

13:49-13:15

2 stops17h 26m

£768

BristolChicago

BRS - MDW

BRSMDW

Bristol

Sat 20/6

06:15-22:17

2 stops22h 02m

Chicago Midway

Sun 28/6

18:58-22:05

2 stops21h 07m

£774

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 8/6

06:15-18:18

2 stops18h 03m

Chicago Midway

Mon 15/6

13:26-13:15

2 stops17h 49m

£778

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sat 7/11

13:25-21:45

1 stop14h 20m

Chicago Midway

Sat 14/11

13:00-10:10

2 stops15h 10m

£788

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 8/6

08:55-09:14

3 stops30h 19m

Chicago Midway

Mon 15/6

09:17-23:05

3 stops31h 48m

£793

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 30/6

06:15-18:31

2 stops18h 16m

Chicago Midway

Tue 7/7

09:49-10:15

2 stops18h 26m

£816

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 15/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Tue 20/10

12:30-10:00

2 stops15h 30m

£818

Flights are sorted by cheapest return flights first.

Deals found on 11/5

Showing 1-10 of 33 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 £736, Delta can have you in Chicago Midway Airport from Wales in 18h 36m. 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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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.

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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