Cheap flights from York to Chicago Midway Airport from £311

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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — MDW
12 Oct — 19 Oct1
1 adult
1 adult, Economy

Cheap 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 September 2025.

Round-trip from

£490

One-way from

£311

Popular in

July

Cheapest in

February

Average price

£508
Virgin Atlantic
  • Virgin Atlantic
  • 7/11-14/11
  • 2 total stops
  • 25h 45m total
  • York to Chicago
3/10
  • 3/10
  • 3 total stops
  • 44h 06m total
  • York to Chicago
Highest demand for flights based on searches. 15% potential increase in price (£78 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (£11 potential savings vs. average return price).
Average for round-trip flights in September 2025

Find flight deals from York to Midway

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 September 2025.

Fri 7/1113:25MAN - MDW
1 stop14h 49mVirgin Atlantic
Fri 14/1117:34MDW - MAN
1 stop10h 56mVirgin Atlantic
Deal found 11/9£490
Sat 15/1113:40MAN - MDW
2 stops15h 52mVirgin Atlantic
Tue 18/1109:32MDW - MAN
2 stops18h 38mVirgin Atlantic
Deal found 10/9£497
Wed 12/1105:50MAN - MDW
2 stops16h 49mVirgin Atlantic
Mon 17/1109:32MDW - MAN
2 stops18h 38mVirgin Atlantic
Deal found 12/9£501
Thu 2/1012:35MAN - MDW
1 stop15h 01mVirgin Atlantic
Mon 13/1010:35MDW - MAN
1 stop16h 00mVirgin Atlantic
Deal found 12/9£503
Fri 14/1113:25MAN - MDW
1 stop16h 07mDelta
Mon 17/1113:47MDW - MAN
2 stops14h 23mDelta
Deal found 11/9£510
Wed 12/1113:30MAN - MDW
1 stop16h 02mDelta
Mon 17/1113:14MDW - MAN
2 stops14h 56mDelta
Deal found 12/9£511
Fri 14/1120:40MAN - MDW
2 stops27h 38mVirgin Atlantic
Mon 17/1113:14MDW - MAN
2 stops14h 56mVirgin Atlantic
Deal found 11/9£512
Wed 12/1113:30MAN - MDW
1 stop16h 02mDelta
Sun 16/1106:00MDW - MAN
1 stop18h 30mDelta
Deal found 12/9£514
Sat 15/1113:30MAN - MDW
1 stop16h 02mDelta
Tue 18/1112:47MDW - MAN
1 stop15h 43mDelta
Deal found 10/9£515
Wed 12/1120:40MAN - MDW
2 stops27h 38mVirgin Atlantic
Sun 16/1109:32MDW - MAN
2 stops16h 48mVirgin Atlantic
Deal found 12/9£516

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 September 2025.
Use the filters below to find and compare flights from York to Chicago Midway Airport that are best for you.

Fly from

York

Fly to

Midway

Route

Depart

Return

Price

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 12/11

05:50-16:39

2 stops16h 49m

Chicago Midway

Mon 17/11

09:32-10:10

2 stops18h 38m

£501

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 14/11

13:25-23:32

1 stop16h 07m

Chicago Midway

Mon 17/11

13:47-10:10

2 stops14h 23m

£510

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sat 15/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Tue 18/11

13:47-10:10

2 stops14h 23m

£511

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 12/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Mon 17/11

13:14-10:10

2 stops14h 56m

£511

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 14/11

20:40-18:18

2 stops27h 38m

Chicago Midway

Mon 17/11

13:14-10:10

2 stops14h 56m

£512

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 12/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Sun 16/11

13:14-10:10

2 stops14h 56m

£515

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 12/11

20:40-18:18

2 stops27h 38m

Chicago Midway

Sun 16/11

09:32-08:20

2 stops16h 48m

£516

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 22/9

12:35-21:36

1 stop15h 01m

Chicago Midway

Thu 2/10

18:15-16:55

2 stops16h 40m

£518

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 23/9

12:35-17:35

1 stop35h 00m

Chicago Midway

Thu 2/10

18:15-13:25

2 stops13h 10m

£518

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 5/3

13:30-21:46

1 stop14h 16m

Chicago Midway

Mon 9/3

13:00-06:40

2 stops12h 40m

£520

Flights are sorted by cheapest return flights first.

Deals found on 10/9

Showing 1-10 of 15 results
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 September 2025.
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.

Comfort

7.3

Entertainment

7.5

Overall

7.4

Food

6.9

Crew

8.1

Boarding

7.7

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!

Comfort

7.3

Entertainment

7.5

Overall

7.4

Food

6.9

Crew

8.1

Boarding

7.7

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 16h 07m. 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

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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 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£486Average£599FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

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