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Cheap flights from York to Chicago from £249

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 28/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
7 May — 14 May1
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 7 April 2026.

Thu 16/420:55
MAN
-
ORD
2 stops25h 05m
Multiple Airlines
Fri 1/522:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 3/4£507
Tue 21/412:45
MAN
-
ORD
2 stops33h 15m
Multiple Airlines
Fri 24/422:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 7/4£521
Tue 21/419:40
MAN
-
ORD
2 stops26h 20m
Multiple Airlines
Tue 28/419:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 4/4£523
Wed 14/1009:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sat 24/1020:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 6/4£528
Mon 11/522:35
MAN
-
ORD
2 stops27h 05m
Multiple Airlines
Mon 18/509:55
ORD
-
MAN
2 stops30h 25m
Multiple Airlines
Deal found 7/4£537
Thu 22/1009:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Fri 30/1020:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 5/4£538
Sun 15/1120:30
MAN
-
ORD
2 stops26h 15m
Scandinavian Airlines
Sun 22/1119:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 6/4£543
Tue 5/507:30
MAN
-
ORD
1 stop12h 30m
Multiple Airlines
Tue 12/521:00
ORD
-
MAN
1 stop14h 25m
Multiple Airlines
Deal found 4/4£545
Mon 18/508:10
MAN
-
MDW
2 stops15h 46m
Multiple Airlines
Mon 25/509:22
MDW
-
MAN
2 stops29h 03m
Multiple Airlines
Deal found 3/4£718
Mon 4/505:55
MAN
-
MDW
2 stops18h 03m
Delta
Tue 12/513:59
MDW
-
MAN
2 stops14h 01m
Delta
Deal found 5/4£727
Wed 6/510:40
MAN
-
MDW
1 stop17h 48m
Delta
Wed 13/513:22
MDW
-
MAN
2 stops12h 53m
Delta
Deal found 5/4£729
Wed 16/905:55
MAN
-
MDW
2 stops18h 36m
Delta
Wed 23/909:30
MDW
-
MAN
2 stops16h 45m
Delta
Deal found 5/4£730

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 7 April 2026.

Round-trip from

£507

One-way from

£249

Popular in

July

Cheapest in

February

Average price

£566
17/4-21/4
  • 17/4-21/4
  • 4 total stops
  • 51h 40m total
  • York to Chicago
Search Deals
28/4
  • 28/4
  • 2 total stops
  • 45h 57m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£79 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 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 7 April 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

Fri 22/5

20:25-21:56

2 stops31h 31m

Chicago O'Hare Intl

Fri 29/5

07:00-08:55

2 stops19h 55m

£711

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

£730

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 7/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Mon 14/9

18:45-16:45

2 stops16h 00m

£730

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 7/9

11:10-22:06

2 stops16h 56m

Chicago O'Hare Intl

Mon 14/9

19:35-16:45

2 stops15h 10m

£730

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sat 2/5

05:55-18:36

2 stops18h 41m

Chicago Midway

Sat 9/5

13:59-10:00

2 stops14h 01m

£791

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 7/5

05:55-17:56

2 stops18h 01m

Chicago Midway

Sun 10/5

13:22-10:10

2 stops14h 48m

£795

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 10/9

11:10-21:36

2 stops16h 26m

Chicago O'Hare Intl

Fri 18/9

13:15-10:20

2 stops15h 05m

£796

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 18/7

19:15-16:00

1 stop26h 45m

Chicago O'Hare Intl

Wed 29/7

16:40-17:05

1 stop18h 25m

£800
Fastest return journey

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 20/5

10:35-18:15

1 stop13h 40m

Chicago O'Hare Intl

Wed 27/5

13:18-10:10

2 stops14h 52m

£816

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Sat 26/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Sun 4/10

17:59-14:00

2 stops14h 01m

£820

Flights are sorted by cheapest return flights first.

Deals found on 4/4

Showing 1-10 of 41 resultsSorted by cheapest first
1
2
3
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5

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 far ahead should I book a flight from York to Chicago?

Use this chart to determine the optimal time to book a return flight from York to Chicago. Price data was last updated on 3 April 2026.

The price you pay for your flight from York to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 59 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from York to Chicago?

Currently, January is the cheapest month in which you can book a flight from York to Chicago (average of £104). Flying from York to Chicago in July is currently the most expensive (average of £556). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

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 7 April 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
685 reviews
Check prices

Entertainment

7.5

Food

6.9

Boarding

7.7

Crew

8.1

Overall

7.5

Comfort

7.3

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

Entertainment

7.5

Food

6.9

Boarding

7.7

Crew

8.1

Overall

7.5

Comfort

7.3

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!
Scandinavian Airlines
7.3
Good
1,746 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Entertainment

7.5

Food

6.9

Boarding

7.7

Crew

8.1

Overall

7.5

Comfort

7.3

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!
Aer Lingus
7.2
Good
1,499 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Entertainment

7.5

Food

6.9

Boarding

7.7

Crew

8.1

Overall

7.5

Comfort

7.3

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!
Icelandair
7.0
Good
631 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Entertainment

7.5

Food

6.9

Boarding

7.7

Crew

8.1

Overall

7.5

Comfort

7.3

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!
British Airways
6.7
Okay
7,859 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Entertainment

7.5

Food

6.9

Boarding

7.7

Crew

8.1

Overall

7.5

Comfort

7.3

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 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, Delta, and TAP AIR PORTUGAL fly from York to Chicago in about 18h 36m. The time it takes to get you to your destination can typically vary by up to 12h 55m. 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.

  • What is the cheapest month to book a flight from York to Chicago?

    Currently, January is the cheapest month in which you can book a flight from York to Chicago (average of £104). Flying from York to Chicago in July is currently the most expensive (average of £556). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 7 April 2026.
AirlineCheapestAverageFlexibilityOn-time
RyanairCheapest£38Average£49FlexibilityNo cancel feeOn-timeN/A
Search Ryanair flights
Scandinavian AirlinesCheapest£384Average£480FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£417Average£577FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
KLMCheapest£459Average£688FlexibilityNo cancel feeOn-time75%
Search KLM flights
FinnairCheapest£471Average£817FlexibilityNo cancel feeOn-time76%
Search Finnair flights
British AirwaysCheapest£477Average£646FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Aer LingusCheapest£481Average£707FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
LufthansaCheapest£488Average£696FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Virgin AtlanticCheapest£504Average£630FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£508Average£661FlexibilityNo cancel feeOn-time69%
Search United 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.

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