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Cheap flights from York to Chicago Midway Airport from £358

MAN — MDW
14 Oct — 21 Oct1
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

Sun 1/1106:00 -
2 stops18h 00m
Tue 17/1113:31 -
2 stops14h 34m
Deal found 10/9£650
Fri 6/1114:55 -
1 stop13h 38m
Wed 11/1113:05 -
1 stop13h 40m
Deal found 11/9£661
Sat 7/1112:40 -
1 stop15h 53m
Sun 15/1117:13 -
2 stops22h 17m
Deal found 11/9£670
Sun 1/1106:00 -
2 stops18h 00m
Sat 14/1112:30 -
2 stops15h 35m
Deal found 13/9£672
Sat 7/1105:50 -
2 stops16h 57m
Sun 22/1113:31 -
2 stops14h 34m
Deal found 14/9£678
Fri 2/1013:00 -
1 stop15h 44m
Fri 16/1006:04 -
1 stop20h 46m
Deal found 10/9£680
Wed 28/1005:50 -
2 stops17h 10m
Wed 11/1112:30 -
2 stops15h 35m
Deal found 13/9£687
Thu 10/1209:05 -
2 stops14h 56m
Tue 15/1212:39 -
2 stops15h 51m
Deal found 13/9£688
Mon 21/905:55 -
2 stops18h 24m
Tue 6/1012:49 -
1 stop14h 01m
Deal found 11/9£689
Wed 23/905:55 -
2 stops18h 38m
Wed 30/913:19 -
2 stops14h 51m
Deal found 12/9£690

Find flight deals from York to Midway

Round-trip from

£650

One-way from

£358

Popular in

July

Cheapest in

February

Average price

£618
Virgin Atlantic
  • Virgin Atlantic
  • 1/11-17/11
  • 4 total stops
  • 32h 34m total
  • York to Chicago
Search Deals
24/9-31/12
  • 24/9-31/12
  • 3 total stops
  • 49h 20m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£82 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 September 2026
Search Deals

Cheapflights Fare Finder

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

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Route

Depart

Return

Price

Cheapest return flight

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Sun 11/10

18:55-11:00

3 stops46h 05m

Chicago Midway

Wed 31/12

00:00-07:00

Nonstop0h 00m

£425

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Sun 7/3

05:50-18:37

2 stops18h 47m

Chicago Midway

Wed 31/12

00:00-07:00

Nonstop0h 00m

£509
Fastest return journey

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 21/1

14:55-22:10

1 stop13h 15m

Chicago Midway

Wed 31/12

00:00-07:00

Nonstop0h 00m

£513

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Mon 14/12

05:50-18:01

2 stops18h 11m

Chicago Midway

Wed 31/12

00:00-07:00

Nonstop0h 00m

£530

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Wed 30/9

13:20-23:44

3 stops40h 24m

Chicago Midway

Wed 31/12

00:00-07:00

Nonstop0h 00m

£553

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Sat 7/11

05:50-16:47

2 stops16h 57m

Chicago Midway

Sun 22/11

13:31-10:05

2 stops14h 34m

£678

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Fri 6/11

14:55-22:33

1 stop13h 38m

Chicago Midway

Wed 11/11

12:30-10:05

2 stops15h 35m

£678

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 18/2

14:55-22:10

1 stop13h 15m

Chicago Midway

Tue 23/2

12:30-10:05

2 stops15h 35m

£685

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Fri 25/9

05:50-18:33

2 stops18h 43m

Chicago Midway

Fri 23/10

13:27-10:10

2 stops14h 43m

£696

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Wed 14/10

05:55-16:47

2 stops16h 52m

Chicago Midway

Mon 19/10

13:27-08:25

2 stops12h 58m

£740

Flights are sorted by cheapest return flights first.

Deals found on 10/9

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

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

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
694 reviews
Check prices

Entertainment

7.5

Comfort

7.3

Boarding

7.7

Overall

7.4

Food

6.9

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.
Virgin Atlantic
7.4
Good
694 reviews
Virgin Atlantic
7.4
Good
694 reviews
Check prices

Entertainment

7.5

Comfort

7.3

Boarding

7.7

Overall

7.4

Food

6.9

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.

Related info for your journey

  • How long is the flight from York to Chicago Midway Airport?

    Departing from York to Chicago Midway Airport will take you 16h 57m. 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

Top airline flying from York to Midway

AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£617Average£725FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

Fly with Cheapflights

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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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