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Cheap flights from York to Chicago Midway Airport from £314

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 14/9. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — MDW
16 Aug — 23 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from York to Midway

Enter your travel dates to find the best prices.

Cheapest flights from York to Midway
Explore the most affordable flight options available from York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 July 2026.

Wed 7/1005:55
MAN
-
MDW
2 stops18h 10m
Virgin Atlantic
Wed 14/1013:28
MDW
-
MAN
2 stops12h 57m
Virgin Atlantic
Deal found 14/7£694
Wed 16/905:55
MAN
-
MDW
2 stops18h 38m
Virgin Atlantic
Wed 23/909:29
MDW
-
MAN
2 stops18h 41m
Virgin Atlantic
Deal found 17/7£700
Tue 25/813:00
MAN
-
MDW
1 stop15h 47m
Multiple Airlines
Mon 31/806:05
MDW
-
MAN
2 stops21h 55m
Multiple Airlines
Deal found 16/7£702
Sun 6/911:15
MAN
-
MDW
1 stop17h 32m
Multiple Airlines
Mon 14/912:03
MDW
-
MAN
1 stop14h 47m
Multiple Airlines
Deal found 13/7£713
Fri 28/813:00
MAN
-
MDW
1 stop15h 47m
Multiple Airlines
Sun 6/911:50
MDW
-
MAN
2 stops20h 10m
Multiple Airlines
Deal found 13/7£722
Tue 8/908:55
MAN
-
MDW
2 stops15h 24m
Delta
Mon 30/1113:00
MDW
-
MAN
2 stops15h 05m
Delta
Deal found 13/7£724
Wed 16/908:55
MAN
-
MDW
2 stops15h 24m
Delta
Wed 23/919:01
MDW
-
MAN
2 stops15h 44m
Delta
Deal found 14/7£725
Mon 7/905:55
MAN
-
MDW
2 stops18h 06m
Delta
Mon 14/913:19
MDW
-
MAN
2 stops14h 51m
Delta
Deal found 13/7£728
Tue 22/920:50
MAN
-
MDW
2 stops27h 43m
Virgin Atlantic
Sun 27/909:29
MDW
-
MAN
2 stops18h 41m
Virgin Atlantic
Deal found 17/7£731

Find flight deals from York to Midway

Keep the following information in mind while searching for York to Midway flight deals. Data was last updated 17 July 2026.

Round-trip from

£694

One-way from

£314

Popular in

July

Cheapest in

February

Average price

£805
Virgin Atlantic
  • Virgin Atlantic
  • 7/10-14/10
  • 4 total stops
  • 31h 07m total
  • York to Chicago
Search Deals
14/9
  • 14/9
  • 3 total stops
  • 50h 25m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (£90 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (£14 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from York 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 17 July 2026.
Use the filters below to find and compare flights from York 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 28/10

05:50-16:39

2 stops15h 49m

Chicago Midway

Wed 11/11

12:30-10:05

2 stops15h 35m

£724

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

08:55-18:19

2 stops15h 24m

Chicago Midway

Wed 23/9

19:01-16:45

2 stops15h 44m

£725
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

08:55-18:19

2 stops15h 24m

Chicago Midway

Wed 16/9

13:19-08:25

2 stops13h 06m

£728

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 8/10

05:55-18:05

2 stops18h 10m

Chicago Midway

Wed 14/10

12:28-08:25

2 stops13h 57m

£756

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 24/9

05:55-18:33

2 stops18h 38m

Chicago Midway

Wed 7/10

13:28-08:25

2 stops12h 57m

£756

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 10/9

08:55-18:19

2 stops15h 24m

Chicago Midway

Wed 23/9

13:19-10:10

2 stops14h 51m

£760

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 8/10

05:55-18:05

2 stops18h 10m

Chicago Midway

Sun 11/10

10:58-07:15

1 stop14h 17m

£786
Cheapest one-way

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 15/9

20:05-11:00

3 stops44h 55m

£377

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 27/7

22:35-09:40

2 stops41h 05m

£450

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 8/9

05:55-16:57

2 stops17h 02m

£460

Flights are sorted by cheapest return flights first.

Deals found on 17/7

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Best time to book a flight from York to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from York 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 York to Chicago Midway Airport

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 17 July 2026.
Read through reviews of airlines operating flights from York to Chicago Midway Airport, such as Virgin Atlantic. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Virgin Atlantic
7.5
Good
693 reviews
Check prices

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.
Virgin Atlantic
7.5
Good
693 reviews
Virgin Atlantic
7.5
Good
693 reviews
Check prices

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.

Related info for your journey

Find useful and relevant information for your journey from York 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 York to Chicago Midway Airport?

    Departing from York to Chicago Midway Airport will take you 15h 49m. There are 3816 mi between York and Chicago Midway Airport.

  • Can I find deals for flights from York to Midway that include hotel bookings?

    Yes. In addition to deals on York to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from York to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from York to Midway.

  • Can I find deals for business class flights from York to Midway?

    Yes. Cheapflights offers flight deals from York 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from York to Midway

Discover the top airline that operate flights from York to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 17 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£532Average£727FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

Fly with Cheapflights

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How does Cheapflights help users find flights from York to Midway?

Cheapflights helps you search for flights from York to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from York to Midway?

Millions of users choose and trust Cheapflights to book the best flight deals from York 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 York to Midway with no change fees?

Certainly. Search results for flights to Midway from York shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Yes! Start tracking prices for York to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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