Find flights
When to book
Airlines
FAQs

Cheap flights from York to Chicago Midway Airport from £263

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 20/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — MDW
2 May — 9 May1
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 2 April 2026.

Sun 10/508:10
MAN
-
MDW
2 stops31h 35m
Multiple Airlines
Tue 26/510:30
MDW
-
MAN
1 stop19h 10m
Multiple Airlines
Deal found 2/4£649
Tue 3/1105:50
MAN
-
MDW
2 stops18h 47m
Virgin Atlantic
Tue 10/1113:00
MDW
-
MAN
2 stops15h 10m
Virgin Atlantic
Deal found 1/4£715
Mon 27/413:00
MAN
-
MDW
1 stop15h 28m
Delta
Mon 4/513:24
MDW
-
MAN
2 stops18h 36m
Delta
Deal found 30/3£716
Wed 29/410:40
MAN
-
MDW
1 stop17h 48m
Virgin Atlantic
Tue 5/509:27
MDW
-
MAN
2 stops18h 43m
Virgin Atlantic
Deal found 1/4£719
Tue 28/413:00
MAN
-
MDW
1 stop15h 28m
Delta
Thu 7/513:22
MDW
-
MAN
2 stops14h 48m
Delta
Deal found 29/3£720
Wed 29/405:55
MAN
-
MDW
2 stops18h 41m
Virgin Atlantic
Wed 6/509:27
MDW
-
MAN
2 stops16h 58m
Virgin Atlantic
Deal found 29/3£721
Sun 3/511:15
MAN
-
MDW
2 stops31h 45m
Multiple Airlines
Fri 29/515:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 29/3£724
Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/910:35
MDW
-
MAN
2 stops15h 40m
Delta
Deal found 31/3£727

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 2 April 2026.

Round-trip from

£649

One-way from

£263

Popular in

July

Cheapest in

February

Average price

£564
10/5-26/5
  • 10/5-26/5
  • 3 total stops
  • 50h 45m total
  • York to Chicago
Search Deals
20/4
  • 20/4
  • 2 total stops
  • 32h 30m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£78 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£12 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 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 2 April 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

Mon 27/4

13:00-22:28

1 stop15h 28m

Chicago Midway

Mon 4/5

13:24-14:00

2 stops18h 36m

£716

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 27/4

13:00-22:28

1 stop15h 28m

Chicago Midway

Mon 4/5

10:41-08:50

1 stop16h 09m

£752

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sun 10/5

20:45-16:12

2 stops25h 27m

Chicago Midway

Tue 26/5

13:22-08:50

2 stops13h 28m

£783

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 15/4

10:40-22:28

1 stop17h 48m

Chicago Midway

Wed 29/4

12:52-07:15

1 stop12h 23m

£784

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 24/4

08:55-18:36

2 stops15h 41m

Chicago Midway

Mon 4/5

13:24-08:50

2 stops13h 26m

£813

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 14/4

13:00-22:28

1 stop15h 28m

Chicago Midway

Tue 28/4

13:24-08:50

2 stops13h 26m

£816

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 14/4

05:55-17:58

2 stops18h 03m

Chicago Midway

Tue 28/4

09:27-08:20

2 stops16h 53m

£816

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 17/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Thu 24/9

17:59-14:00

2 stops14h 01m

£817

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 30/6

05:55-16:46

2 stops16h 51m

Chicago Midway

Tue 7/7

11:05-08:50

1 stop15h 45m

£836

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 11/5

05:55-17:56

2 stops18h 01m

Chicago Midway

Sun 24/5

09:22-08:15

2 stops16h 53m

£840

Flights are sorted by cheapest return flights first.

Deals found on 29/3

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 2 April 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
685 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.5

Comfort

7.3

Food

6.9

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
685 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.5

Comfort

7.3

Food

6.9

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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 2 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£508Average£632FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.