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Cheap flights from York to Chicago from £289

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 27/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
23 Apr — 30 Apr1
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 24 March 2026.

Thu 14/514:25
MAN
-
ORD
2 stops31h 45m
Multiple Airlines
Thu 28/519:15
ORD
-
MAN
2 stops20h 40m
Multiple Airlines
Deal found 22/3£447
Sun 22/1110:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 29/1119:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 20/3£456
Thu 21/509:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Thu 28/519:15
ORD
-
MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 19/3£466
Tue 19/519:10
MAN
-
ORD
1 stop27h 00m
Scandinavian Airlines
Tue 2/619:15
ORD
-
MAN
2 stops32h 25m
Scandinavian Airlines
Deal found 19/3£467
Fri 6/1119:15
MAN
-
ORD
1 stop27h 30m
Scandinavian Airlines
Sat 14/1119:20
ORD
-
MAN
2 stops34h 55m
Scandinavian Airlines
Deal found 22/3£469
Sun 19/417:30
MAN
-
MDW
2 stops31h 06m
Virgin Atlantic
Sun 26/413:24
MDW
-
MAN
2 stops36h 51m
Virgin Atlantic
Deal found 22/3£672
Tue 10/1113:30
MAN
-
MDW
1 stop14h 15m
Virgin Atlantic
Tue 24/1113:00
MDW
-
MAN
2 stops13h 20m
Virgin Atlantic
Deal found 21/3£674
Wed 29/410:40
MAN
-
MDW
1 stop17h 48m
Virgin Atlantic
Sat 2/517:21
MDW
-
MAN
1 stop31h 54m
Virgin Atlantic
Deal found 20/3£690
Wed 16/905:55
MAN
-
MDW
2 stops16h 32m
Delta
Wed 23/910:35
MDW
-
MAN
2 stops15h 40m
Delta
Deal found 19/3£693
Mon 20/405:55
MAN
-
MDW
2 stops18h 03m
Delta
Mon 27/413:24
MDW
-
MAN
2 stops13h 26m
Delta
Deal found 21/3£702
Tue 5/513:00
MAN
-
MDW
1 stop15h 28m
Multiple Airlines
Tue 12/513:22
MDW
-
MAN
2 stops13h 03m
Multiple Airlines
Deal found 21/3£705
Thu 12/1105:50
MAN
-
MDW
2 stops18h 20m
Virgin Atlantic
Wed 13/113:00
MDW
-
MAN
2 stops15h 10m
Virgin Atlantic
Deal found 19/3£706

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 24 March 2026.

Round-trip from

£447

One-way from

£289

Popular in

July

Cheapest in

February

Average price

£567
14/5-28/5
  • 14/5-28/5
  • 4 total stops
  • 52h 25m total
  • York to Chicago
Search Deals
27/4
  • 27/4
  • 3 total stops
  • 35h 15m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£77 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 March 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 24 March 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

Tue 19/5

12:45-16:10

2 stops33h 25m

Chicago O'Hare Intl

Tue 2/6

19:15-09:40

2 stops32h 25m

£470

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 10/5

19:30-16:10

1 stop26h 40m

Chicago O'Hare Intl

Thu 28/5

19:15-08:55

1 stop31h 40m

£603
Fastest return journey

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 16/4

13:05-18:15

1 stop11h 10m

Chicago O'Hare Intl

Thu 23/4

19:25-11:40

1 stop10h 15m

£607

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 12/5

19:10-16:10

1 stop27h 00m

Chicago O'Hare Intl

Tue 26/5

19:15-18:30

1 stop17h 15m

£619

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 17/4

13:05-18:15

1 stop11h 10m

Chicago O'Hare Intl

Sun 19/4

19:25-11:40

1 stop10h 15m

£633

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 22/5

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Mon 25/5

19:15-19:10

2 stops17h 55m

£654

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 17/4

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Sun 19/4

06:04-19:45

2 stops31h 41m

£670

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-16:27

2 stops16h 32m

Chicago Midway

Wed 23/9

10:35-08:15

2 stops15h 40m

£693

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 4/5

06:00-16:56

2 stops16h 56m

Chicago O'Hare Intl

Mon 11/5

12:55-09:50

2 stops14h 55m

£699

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 6/5

05:55-17:58

2 stops18h 03m

Chicago Midway

Wed 13/5

13:59-10:00

2 stops14h 01m

£706

Flights are sorted by cheapest return flights first.

Deals found on 20/3

Showing 1-10 of 39 resultsSorted by cheapest first
1
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 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 13 March 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 £103). Flying from York to Chicago in July is currently the most expensive (average of £572). 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.

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 24 March 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

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.5

Food

6.9

Entertainment

7.5

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

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.5

Food

6.9

Entertainment

7.5

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
1,722 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.5

Food

6.9

Entertainment

7.5

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
1,487 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.5

Food

6.9

Entertainment

7.5

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
625 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.5

Food

6.9

Entertainment

7.5

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
7,818 reviews
Virgin Atlantic
7.5
Good
685 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.5

Food

6.9

Entertainment

7.5

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, Icelandair, and Delta fly from York to Chicago in about 11h 10m. The time it takes to get you to your destination can typically vary by up to 22h 15m. York and Chicago are separated by a distance of 3812 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from York to Chicago one-way?

    £345 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on Scandinavian Airlines and Aer Lingus, with prices starting from £403 and £487, respectively.

  • 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 £103). Flying from York to Chicago in July is currently the most expensive (average of £572). 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 24 March 2026.
AirlineCheapestAverageFlexibilityOn-time
RyanairCheapest£37Average£48FlexibilityNo cancel feeOn-timeN/A
Search Ryanair flights
Scandinavian AirlinesCheapest£380Average£473FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£408Average£556FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
KLMCheapest£455Average£681FlexibilityNo cancel feeOn-time75%
Search KLM flights
FinnairCheapest£466Average£808FlexibilityNo cancel feeOn-time76%
Search Finnair flights
British AirwaysCheapest£468Average£616FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Aer LingusCheapest£477Average£699FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
LufthansaCheapest£483Average£688FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Virgin AtlanticCheapest£499Average£623FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£500Average£631FlexibilityNo 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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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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