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Cheap flights from York to Chicago from £248

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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
27 Aug — 3 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from York to Chicago
Explore the most affordable flight options available from York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 July 2026.

Wed 16/913:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Sat 10/1019:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 27/7£507
Thu 10/914:25
MAN
-
ORD
3 stops31h 45m
Multiple Airlines
Thu 17/919:15
ORD
-
MAN
2 stops20h 40m
Multiple Airlines
Deal found 27/7£508
Sat 31/1020:55
MAN
-
ORD
2 stops24h 35m
Multiple Airlines
Thu 5/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/7£510
Fri 30/1006:35
MAN
-
ORD
2 stops16h 45m
Multiple Airlines
Sun 8/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/7£510
Mon 2/1111:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Sat 7/1118:30
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 27/7£512
Sat 31/1010:30
MAN
-
ORD
1 stop31h 27m
Lufthansa
Thu 5/1121:50
ORD
-
MAN
1 stop13h 05m
Lufthansa
Deal found 27/7£513
Tue 3/1119:00
MAN
-
ORD
2 stops26h 30m
Multiple Airlines
Sat 7/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/7£516
Thu 29/1011:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Tue 3/1118:30
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 27/7£521
Tue 22/909:10
MAN
-
ORD
2 stops34h 00m
Multiple Airlines
Tue 29/915:00
ORD
-
MAN
2 stops23h 10m
Multiple Airlines
Deal found 27/7£526
Wed 16/916:00
MAN
-
ORD
2 stops31h 50m
Multiple Airlines
Thu 8/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/7£531
Tue 15/917:50
MAN
-
ORD
2 stops26h 35m
Multiple Airlines
Sat 10/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/7£532
Mon 31/820:50
MAN
-
MDW
2 stops26h 09m
Virgin Atlantic
Wed 9/909:29
MDW
-
MAN
2 stops16h 56m
Virgin Atlantic
Deal found 25/7£698

Find flight deals from York to Chicago

Keep the following information in mind while searching for York to Chicago flight deals. Data was last updated 28 July 2026.

Round-trip from

£507

One-way from

£248

Popular in

July

Cheapest in

February

Average price

£805
Icelandair
  • Icelandair
  • 16/9-10/10
  • 2 total stops
  • 21h 25m total
  • York to Chicago
Search Deals
8/9
  • 8/9
  • 3 total stops
  • 42h 15m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (£96 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£13 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from York to Chicago 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 July 2026.
Use the filters below to find and compare flights from York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 12/11

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Fri 27/11

19:15-08:40

2 stops31h 25m

£544

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 16/9

21:10-16:10

2 stops25h 00m

Chicago O'Hare Intl

Wed 23/9

19:15-18:30

1 stop17h 15m

£578

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 5/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Sun 18/10

19:15-19:45

2 stops18h 30m

£578

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 7/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Wed 14/10

19:15-09:40

2 stops32h 25m

£580

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 24/9

10:20-16:10

2 stops35h 50m

Chicago O'Hare Intl

Wed 7/10

19:15-20:30

2 stops19h 15m

£617

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 3/9

17:55-16:00

1 stop28h 05m

Chicago O'Hare Intl

Thu 10/9

18:00-10:05

1 stop34h 05m

£690

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 8/9

05:55-16:57

2 stops17h 02m

Chicago Midway

Tue 15/9

09:29-08:25

2 stops16h 56m

£730

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 1/12

05:50-18:37

2 stops18h 47m

Chicago Midway

Sat 5/12

09:30-08:20

2 stops16h 50m

£753
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 8/9

13:00-22:44

1 stop15h 44m

Chicago Midway

Thu 17/9

13:00-08:50

1 stop13h 50m

£757

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 10/9

05:55-18:19

2 stops18h 24m

Chicago Midway

Thu 17/9

19:01-16:45

2 stops15h 44m

£760

Flights are sorted by cheapest return flights first.

Deals found on 23/7

Showing 1-10 of 31 resultsSorted by cheapest first
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2
3
4

Best time to book a flight from York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

How much does it cost for a return flight from York to Chicago?

Airfare is below average for this route at the moment.
York to Chicago flights typically cost between £584 and £839 in September.
The cheapest return price found within the last 5 days was £507 on Icelandair (16 Sept–10 Oct).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 28 July 2026.
Read through reviews of airlines operating flights from York to Chicago, such as Virgin Atlantic,Scandinavian Airlines, andAer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Entertainment

7.5

Boarding

7.7

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
7.5
Good
694 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Entertainment

7.5

Boarding

7.7

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.
Scandinavian Airlines
7.4
Good
1,903 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Entertainment

7.5

Boarding

7.7

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.
Aer Lingus
7.3
Good
1,682 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Entertainment

7.5

Boarding

7.7

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.
Icelandair
7.0
Good
715 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Entertainment

7.5

Boarding

7.7

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.
British Airways
6.7
Okay
8,128 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Entertainment

7.5

Boarding

7.7

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

Find useful and relevant information for your journey from York to Chicago. 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?

    Airlines like Scandinavian Airlines, Virgin Atlantic, and Delta fly from York to Chicago in about 18h 10m. The time it takes to get you to your destination can typically vary by up to 15h 40m. York and Chicago are separated by a distance of 3816 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from York to Chicago that include hotel bookings?

    Yes. In addition to deals on York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from York to Chicago.

  • Can I find deals for business class flights from York to Chicago?

    Yes. Cheapflights offers flight deals from York to Chicago 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 Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from York to Chicago

Discover the top 10 airlines that operate flights from York to Chicago. 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 July 2026.
AirlineCheapestAverageFlexibilityOn-time
RyanairCheapest£36Average£59FlexibilityNo cancel feeOn-timeN/A
Search Ryanair flights
Scandinavian AirlinesCheapest£384Average£523FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£433Average£599FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£469Average£722FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
British AirwaysCheapest£480Average£664FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Virgin AtlanticCheapest£496Average£686FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£505Average£792FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
KLMCheapest£515Average£601FlexibilityNo cancel feeOn-time75%
Search KLM flights
LufthansaCheapest£524Average£735FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
American AirlinesCheapest£566Average£764FlexibilityNo cancel feeOn-time71%
Search American Airlines 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 Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from York to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from York to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from York to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from York to Chicago with no change fees?

Certainly. Search results for flights to Chicago 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 Chicago become cheaper?

Not ready to book yet? You can track prices for flights from York to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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