Find flights
When to book
Airlines
FAQs

Cheap flights from York to Chicago Midway Airport from £266

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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — MDW
28 May — 4 Jun1
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 28 April 2026.

Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/909:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 24/4£727
Wed 9/910:40
MAN
-
MDW
2 stops28h 02m
Delta
Tue 15/906:00
MDW
-
MAN
2 stops20h 20m
Delta
Deal found 27/4£729
Mon 7/905:55
MAN
-
MDW
2 stops18h 10m
Delta
Tue 15/913:00
MDW
-
MAN
2 stops13h 25m
Delta
Deal found 26/4£730
Wed 28/1005:50
MAN
-
MDW
2 stops20h 55m
Virgin Atlantic
Wed 11/1113:05
MDW
-
MAN
1 stop15h 25m
Virgin Atlantic
Deal found 27/4£735
Sat 12/913:15
MAN
-
MDW
1 stop14h 31m
Virgin Atlantic
Thu 24/913:05
MDW
-
MAN
1 stop13h 45m
Virgin Atlantic
Deal found 25/4£751
Thu 8/1013:00
MAN
-
MDW
1 stop14h 45m
Virgin Atlantic
Tue 20/1013:05
MDW
-
MAN
1 stop13h 45m
Virgin Atlantic
Deal found 28/4£753
Thu 17/913:00
MAN
-
MDW
1 stop14h 46m
Delta
Mon 28/917:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 27/4£756
Fri 9/1013:00
MAN
-
MDW
1 stop14h 45m
Delta
Wed 14/1009:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 25/4£757
Mon 5/1005:55
MAN
-
MDW
2 stops18h 36m
Delta
Sun 18/1013:00
MDW
-
MAN
2 stops15h 20m
Delta
Deal found 25/4£758
Fri 9/1014:55
MAN
-
MDW
2 stops27h 01m
Multiple Airlines
Mon 12/1006:00
MDW
-
MAN
2 stops20h 15m
Multiple Airlines
Deal found 27/4£758

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 28 April 2026.

Round-trip from

£727

One-way from

£266

Popular in

July

Cheapest in

February

Average price

£555
Delta
  • Delta
  • 16/9-23/9
  • 4 total stops
  • 35h 21m total
  • York to Chicago
Search Deals
17/5
  • 17/5
  • 2 total stops
  • 54h 15m 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. 3% potential price decrease (£13 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 28 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

Wed 16/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Wed 23/9

09:30-08:15

2 stops16h 45m

£727

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-15:27

1 stop34h 47m

Chicago Midway

Wed 16/9

06:00-08:15

2 stops20h 15m

£729

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-21:46

1 stop17h 06m

Chicago Midway

Mon 14/9

06:00-08:15

2 stops20h 15m

£729
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 9/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Wed 14/10

13:00-08:15

2 stops13h 15m

£756

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 5/10

05:55-18:31

2 stops18h 36m

Chicago Midway

Sun 18/10

10:35-07:15

1 stop14h 40m

£759

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-09:50

1 stop29h 10m

Chicago Midway

Sun 13/9

17:59-22:00

2 stops22h 01m

£759

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/9

10:40-08:42

2 stops28h 02m

Chicago Midway

Sat 19/9

16:30-07:15

1 stop32h 45m

£759

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 5/10

05:55-18:31

2 stops18h 36m

Chicago Midway

Sat 17/10

13:00-08:15

2 stops13h 15m

£760

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 6/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Sun 18/10

13:00-10:20

2 stops15h 20m

£789
Cheapest one-way

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 19/5

22:45-14:35

3 stops45h 50m

£402

Flights are sorted by cheapest return flights first.

Deals found on 24/4

Showing 1-10 of 18 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 28 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
7.4
Good
688 reviews
Check prices

Food

6.9

Overall

7.4

Comfort

7.3

Entertainment

7.5

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!
Virgin Atlantic
7.4
Good
688 reviews
Virgin Atlantic
7.4
Good
688 reviews
Check prices

Food

6.9

Overall

7.4

Comfort

7.3

Entertainment

7.5

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 18h 36m. 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

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 28 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£499Average£621FlexibilityNo 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.