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Cheap flights from York to Chicago Midway Airport from £299

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 17/6. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — MDW
11 Apr — 18 Apr1
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 12 March 2026.

Mon 20/413:00
MAN
-
MDW
1 stop15h 28m
Delta
Mon 27/413:24
MDW
-
MAN
2 stops13h 26m
Delta
Deal found 10/3£658
Tue 14/420:50
MAN
-
MDW
2 stops27h 08m
Virgin Atlantic
Mon 20/413:24
MDW
-
MAN
2 stops12h 51m
Virgin Atlantic
Deal found 7/3£658
Wed 22/410:40
MAN
-
MDW
1 stop17h 48m
Delta
Wed 29/410:41
MDW
-
MAN
2 stops15h 34m
Delta
Deal found 8/3£661
Mon 20/405:50
MAN
-
MDW
2 stops18h 46m
Virgin Atlantic
Mon 27/409:27
MDW
-
MAN
2 stops16h 58m
Virgin Atlantic
Deal found 7/3£664
Mon 7/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Tue 22/910:35
MDW
-
MAN
2 stops15h 45m
Delta
Deal found 7/3£667
Wed 9/910:40
MAN
-
MDW
1 stop17h 06m
Delta
Mon 14/917:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 11/3£668
Mon 20/413:00
MAN
-
MDW
1 stop15h 28m
Delta
Thu 30/409:27
MDW
-
MAN
2 stops16h 58m
Delta
Deal found 10/3£679
Tue 12/505:55
MAN
-
MDW
2 stops18h 38m
Delta
Wed 20/518:36
MDW
-
MAN
2 stops16h 19m
Delta
Deal found 10/3£684
Wed 9/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/917:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 8/3£687
Sun 19/411:15
MAN
-
MDW
1 stop17h 13m
Virgin Atlantic
Mon 27/413:24
MDW
-
MAN
2 stops12h 51m
Virgin Atlantic
Deal found 10/3£688
Sun 19/405:55
MAN
-
MDW
2 stops18h 03m
Delta
Mon 27/418:38
MDW
-
MAN
2 stops16h 07m
Delta
Deal found 10/3£688

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 12 March 2026.

Round-trip from

£658

One-way from

£299

Popular in

July

Cheapest in

February

Average price

£565
Delta
  • Delta
  • 20/4-27/4
  • 3 total stops
  • 28h 54m total
  • York to Chicago
Search Deals
17/6
  • 17/6
  • 3 total stops
  • 48h 50m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£76 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£11 potential savings vs. average return price).
Search Deals
Average for round-trip flights in March 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 12 March 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

Tue 8/9

05:55-18:05

2 stops18h 10m

Chicago Midway

Tue 15/9

10:35-08:20

2 stops15h 45m

£690
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 14/4

13:00-22:28

1 stop15h 28m

Chicago Midway

Mon 20/4

13:24-08:15

2 stops12h 51m

£706

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 13/5

11:00-18:33

2 stops13h 33m

Chicago Midway

Thu 28/5

13:22-10:20

2 stops14h 58m

£717

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 23/4

13:00-22:28

1 stop15h 28m

Chicago Midway

Sun 26/4

09:27-07:15

2 stops15h 48m

£720

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 16/4

05:55-17:58

2 stops18h 03m

Chicago Midway

Sat 25/4

06:00-08:50

1 stop20h 50m

£721

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 16/4

05:55-17:58

2 stops18h 03m

Chicago Midway

Sun 26/4

09:27-07:15

2 stops15h 48m

£721

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 26/4

11:15-22:28

1 stop17h 13m

Chicago Midway

Sun 3/5

18:38-14:00

2 stops13h 22m

£738

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 6/5

05:55-17:58

2 stops18h 03m

Chicago Midway

Wed 20/5

09:22-07:15

2 stops15h 53m

£772

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 21/5

05:55-17:56

2 stops18h 01m

Chicago Midway

Thu 28/5

13:22-10:20

2 stops14h 58m

£833
Cheapest one-way

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 1/4

12:25-10:15

3 stops27h 50m

£445

Flights are sorted by cheapest return flights first.

Deals found on 8/3

Showing 1-10 of 17 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 12 March 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
680 reviews
Check prices

Boarding

7.7

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Overall

7.5

Reviews

1 / 20
6.0
Good

Pratap,Aug 2025

JFK - LHR

The flight is clean, food good and the staff are excellent! Very professional, polite and accommodating. The seat itself is really mediocre. Can’t believe there is not inch of storage space. Believe it or not it there is not place even to put away your phone or pen!! Very very surprising and terribly inconvenient. No coat hanger hook either. Had to give it away. ALL IN ALL VERY INCONVENIENT business class seat compared to their peers. What is even more surprising is that this on their relatively new fleet of Airbus A350-1000. I was having com platelets different expectations of Virgin and this has disappointed me. Everything else is just as good and as you would expect from Virgin!
Virgin Atlantic
7.5
Good
680 reviews
Virgin Atlantic
7.5
Good
680 reviews
Check prices

Boarding

7.7

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Overall

7.5

Reviews

1 / 20
6.0
Good

Pratap,Aug 2025

JFK - LHR

The flight is clean, food good and the staff are excellent! Very professional, polite and accommodating. The seat itself is really mediocre. Can’t believe there is not inch of storage space. Believe it or not it there is not place even to put away your phone or pen!! Very very surprising and terribly inconvenient. No coat hanger hook either. Had to give it away. ALL IN ALL VERY INCONVENIENT business class seat compared to their peers. What is even more surprising is that this on their relatively new fleet of Airbus A350-1000. I was having com platelets different expectations of Virgin and this has disappointed me. Everything else is just as good and as you would expect from Virgin!

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 28m. There are 3816 mi between York and Chicago Midway Airport. Both multi-stop and direct flights can be found to your destination and back.

  • 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 12 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£503Average£626FlexibilityNo 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?

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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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