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Cheap flights from York to Chicago Midway Airport from £329

MAN — MDW
1 Oct — 8 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

Wed 2/1220:40 -
2 stops27h 21m
Mon 7/1213:41 -
2 stops17h 04m
Deal found 28/8£649
Thu 15/1013:00 -
1 stop33h 14m
Tue 20/1010:59 -
1 stop15h 51m
Deal found 31/8£658
Sun 1/1105:50 -
2 stops18h 10m
Mon 16/1112:30 -
2 stops15h 35m
Deal found 29/8£659
Mon 28/913:00 -
1 stop15h 44m
Mon 5/1019:13 -
2 stops15h 32m
Deal found 29/8£661
Tue 8/913:00 -
1 stop15h 44m
Thu 3/1209:37 -
2 stops16h 43m
Deal found 31/8£670
Wed 23/905:50 -
2 stops18h 29m
Tue 13/1013:27 -
2 stops14h 43m
Deal found 30/8£671
Wed 4/1105:50 -
2 stops16h 57m
Sun 8/1109:29 -
2 stops16h 51m
Deal found 29/8£678
Tue 1/1209:05 -
2 stops14h 56m
Mon 7/1212:39 -
2 stops13h 41m
Deal found 1/9£679
Wed 2/1212:40 -
1 stop16h 15m
Mon 7/1212:39 -
2 stops13h 41m
Deal found 1/9£680

Find flight deals from York to Midway

Round-trip from

£649

One-way from

£329

Popular in

July

Cheapest in

February

Average price

£585
Virgin Atlantic
  • Virgin Atlantic
  • 2/12-7/12
  • 4 total stops
  • 44h 25m total
  • York to Chicago
Search Deals
23/9
  • 23/9
  • 2 total stops
  • 49h 50m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£86 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£13 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.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Wed 16/9

05:55-18:19

2 stops18h 24m

Chicago Midway

Mon 21/9

19:13-16:45

2 stops15h 32m

£690

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Fri 20/11

20:40-16:18

2 stops25h 38m

Chicago Midway

Fri 4/12

12:39-10:30

2 stops15h 51m

£690

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Sat 12/9

05:55-16:57

2 stops17h 02m

Chicago Midway

Sat 26/9

13:19-08:25

2 stops13h 06m

£690

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Wed 16/9

05:55-18:33

2 stops18h 38m

Chicago Midway

Wed 23/9

19:01-16:45

2 stops15h 44m

£690

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Wed 14/10

05:55-18:00

2 stops18h 05m

Chicago Midway

Wed 21/10

13:27-08:25

2 stops12h 58m

£737

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 15/10

05:55-18:00

2 stops18h 05m

Chicago Midway

Tue 20/10

10:59-08:50

1 stop15h 51m

£739

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 8/10

05:55-18:00

2 stops18h 05m

Chicago Midway

Sun 11/10

09:29-08:25

2 stops16h 56m

£774

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Sun 1/11

05:50-19:00

2 stops18h 10m

Chicago Midway

Sun 29/11

06:00-06:40

1 stop18h 40m

£798

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Sun 1/11

11:00-22:33

1 stop17h 33m

Chicago Midway

Mon 16/11

09:30-08:20

2 stops16h 50m

£799
Fastest return journey

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Thu 22/10

13:00-22:33

1 stop15h 33m

Chicago Midway

Sat 7/11

12:27-08:20

2 stops13h 53m

£859

Flights are sorted by cheapest return flights first.

Deals found on 28/8

Showing 1-10 of 20 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
695 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.9

Entertainment

7.5

Overall

7.4

Boarding

7.7

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
695 reviews
Virgin Atlantic
7.4
Good
695 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.9

Entertainment

7.5

Overall

7.4

Boarding

7.7

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 18h 24m. 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£614Average£722FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

Fly with Cheapflights

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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.

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