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Cheap flights from York to Chicago Midway Airport from £245

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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — MDW
11 Feb — 18 Feb1
1 adult
1 adult, Economy, 0 bags

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 January 2026.

Round-trip from

£526

One-way from

£245

Popular in

July

Cheapest in

January

Average price

£38
Delta
  • Delta
  • 2/2-8/2
  • 3 total stops
  • 29h 13m total
  • York to Chicago
Search Deals
1/2
  • 1/2
  • 3 total stops
  • 51h 50m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 21% potential increase in price (£112 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (£29 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find 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 January 2026.

Sat 17/113:30MAN - MDW
1 stop14h 37mVirgin Atlantic
Sat 24/116:30MDW - MAN
1 stop12h 00mVirgin Atlantic
Deal found 9/1£502
Mon 2/209:00MAN - MDW
1 stop14h 29mDelta
Sun 8/213:26MDW - MAN
2 stops14h 44mDelta
Deal found 11/1£526
Tue 24/213:30MAN - MDW
1 stop15h 03mDelta
Tue 3/318:20MDW - MAN
2 stops15h 45mDelta
Deal found 10/1£527
Fri 16/113:25MAN - MDW
1 stop14h 42mDelta
Sat 24/113:26MDW - MAN
2 stops14h 44mDelta
Deal found 9/1£527
Sat 17/113:30MAN - MDW
1 stop14h 37mDelta
Sat 24/113:26MDW - MAN
2 stops14h 44mDelta
Deal found 9/1£528
Fri 6/213:25MAN - MDW
1 stop14h 57mDelta
Wed 11/212:46MDW - MAN
1 stop13h 59mDelta
Deal found 11/1£530
Fri 13/213:25MAN - MDW
1 stop15h 06mVirgin Atlantic
Wed 18/212:45MDW - MAN
1 stop14h 00mVirgin Atlantic
Deal found 9/1£548
Wed 2/905:55MAN - MDW
2 stops18h 36mDelta
Wed 9/913:05MDW - MAN
1 stop12h 10mDelta
Deal found 9/1£551

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 January 2026.
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

Mon 2/2

09:00-17:29

1 stop14h 29m

Chicago Midway

Sun 8/2

13:26-10:10

2 stops14h 44m

£526

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 19/3

13:30-22:31

1 stop14h 01m

Chicago Midway

Mon 23/3

13:10-10:10

2 stops16h 00m

£527

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 1/2

05:50-18:36

2 stops18h 46m

Chicago Midway

Sun 8/2

09:33-10:10

2 stops18h 37m

£527

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 23/1

13:25-22:22

1 stop14h 57m

Chicago Midway

Mon 26/1

13:26-10:10

2 stops14h 44m

£527

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 24/2

05:50-17:37

2 stops17h 47m

Chicago Midway

Tue 3/3

13:29-10:10

2 stops14h 41m

£528

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 23/2

05:50-18:40

2 stops18h 50m

Chicago Midway

Mon 2/3

13:29-10:10

2 stops14h 41m

£529

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 6/2

13:25-22:22

1 stop14h 57m

Chicago Midway

Wed 11/2

12:46-08:45

1 stop13h 59m

£530

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 1/2

14:15-12:05

3 stops51h 50m

£245

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 26/1

13:05-12:05

3 stops53h 00m

£304

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 25/1

19:55-12:05

3 stops46h 10m

£305

Flights are sorted by cheapest return flights first.

Deals found on 8/1

Showing 1-10 of 17 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 January 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
678 reviews
Check prices

Comfort

7.3

Crew

8.2

Food

6.9

Entertainment

7.6

Overall

7.5

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!
Virgin Atlantic
7.5
Good
678 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Comfort

7.3

Crew

8.2

Food

6.9

Entertainment

7.6

Overall

7.5

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 14h 29m. 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

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Alternative routes for York to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£502Average£624FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

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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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