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Cheap flights from York to Chicago from £225

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 22/11. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
15 Nov — 22 Nov1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from York to Chicago are usually found in February or January, booked 59 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from York to Chicago

Keep the following information in mind while searching for York to Chicago flight deals. Data was last updated 16 October 2025.

Round-trip from

£418

One-way from

£225

Popular in

July

Cheapest in

February

Average price

£578
22/11-29/11
  • 22/11-29/11
  • 2 total stops
  • 25h 20m total
  • York to Chicago
Search Deals
22/11
  • 22/11
  • 2 total stops
  • 28h 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 (£11 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find 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 16 October 2025.

Sat 1/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sat 15/1119:20ORD - MAN
2 stops18h 25mScandinavian Airlines
Deal found 16/10£419
Sun 23/1109:20MAN - ORD
2 stops37h 25mScandinavian Airlines
Sun 30/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 16/10£427
Tue 16/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Mon 12/119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 15/10£432
Wed 12/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Wed 19/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 15/10£435
Tue 4/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Sun 9/1119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 15/10£436
Fri 7/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Wed 12/1119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 14/10£454
Mon 15/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Thu 15/119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 15/10£468
Mon 17/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Fri 21/1119:20ORD - MAN
2 stops31h 20mScandinavian Airlines
Deal found 15/10£471
Thu 20/1113:30MAN - MDW
1 stop16h 10mVirgin Atlantic
Sun 7/1210:49MDW - MAN
1 stop13h 41mVirgin Atlantic
Deal found 14/10£639
Tue 4/1113:30MAN - MDW
1 stop14h 44mDelta
Tue 11/1113:47MDW - MAN
2 stops14h 23mDelta
Deal found 14/10£646
Mon 15/1205:50MAN - MDW
2 stops18h 28mDelta
Thu 15/113:00MDW - MAN
2 stops15h 10mDelta
Deal found 15/10£655
Fri 21/1113:25MAN - MDW
1 stop16h 15mDelta
Fri 28/1109:41MDW - MAN
2 stops16h 39mDelta
Deal found 15/10£669

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 16 October 2025.
Use the filters below to find and compare flights from York to Chicago that are best for you.

Fly from

York

Fly to

Chicago

Route

Depart

Return

Price

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/3

19:15-16:55

1 stop27h 40m

Chicago O'Hare Intl

Mon 9/3

20:20-17:55

2 stops16h 35m

£418

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 1/11

10:10-17:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 15/11

19:20-19:45

2 stops18h 25m

£419

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 16/12

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 12/1

19:20-18:35

1 stop17h 15m

£432

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/2

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Fri 13/2

19:20-18:35

1 stop17h 15m

£435

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 7/1

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Wed 4/3

19:20-18:35

1 stop17h 15m

£435

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 12/11

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Wed 19/11

19:20-18:35

1 stop17h 15m

£435

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 17/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 21/11

19:20-08:40

2 stops31h 20m

£471

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Fri 13/2

19:20-18:35

1 stop17h 15m

£477

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 6/1

13:30-21:46

1 stop14h 16m

Chicago Midway

Wed 14/1

13:00-10:10

2 stops15h 10m

£591

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 5/3

13:30-21:46

1 stop14h 16m

Chicago Midway

Mon 9/3

13:00-06:40

2 stops36h 40m

£643

Flights are sorted by cheapest return flights first.

Deals found on 14/10

Showing 1-10 of 33 results
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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 10 October 2025.

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, May is the cheapest month in which you can book a flight from York to Chicago (average of £143). Flying from York to Chicago in July is currently the most expensive (average of £599). 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.

What is the cheapest time of day to fly from Y0R to CHI?

Find hourly flight availability from York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 16 October 2025.

A simple way to save on the total cost of your ticket is to fly from York to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight at midday.

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 16 October 2025.
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
670 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Crew

8.1

Entertainment

7.5

Boarding

7.7

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
670 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Crew

8.1

Entertainment

7.5

Boarding

7.7

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
7.4
Good
1,533 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Crew

8.1

Entertainment

7.5

Boarding

7.7

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
1,341 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Crew

8.1

Entertainment

7.5

Boarding

7.7

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
556 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Crew

8.1

Entertainment

7.5

Boarding

7.7

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
7,457 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Comfort

7.3

Overall

7.5

Food

6.9

Crew

8.1

Entertainment

7.5

Boarding

7.7

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, Virgin Atlantic, and Delta fly from York to Chicago in about 14h 16m. The time it takes to get you to your destination can typically vary by up to 13h 24m. 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, May is the cheapest month in which you can book a flight from York to Chicago (average of £143). Flying from York to Chicago in July is currently the most expensive (average of £599). 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

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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 16 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest£367Average£451FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£374Average£623FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
IcelandairCheapest£418Average£534FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
British AirwaysCheapest£433Average£607FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Aer LingusCheapest£453Average£702FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
KLMCheapest£455Average£596FlexibilityNo cancel feeOn-time75%
Search KLM flights
FinnairCheapest£466Average£707FlexibilityNo cancel feeOn-time76%
Search Finnair flights
LufthansaCheapest£473Average£621FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Virgin AtlanticCheapest£488Average£610FlexibilityNo 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.

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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