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Cheap flights from York to Chicago from £252

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 15/1. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

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 6 November 2025.

Round-trip from

£427

One-way from

£252

Popular in

July

Cheapest in

February

Average price

£554
Scandinavian Airlines
  • Scandinavian Airlines
  • 5/12-12/12
  • 4 total stops
  • 57h 10m total
  • York to Chicago
Search Deals
15/1
  • 15/1
  • 2 total stops
  • 35h 59m total
  • York to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£81 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 November 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 6 November 2025.

Fri 5/1220:55MAN - ORD
2 stops25h 50mScandinavian Airlines
Fri 12/1219:20ORD - MAN
2 stops31h 20mScandinavian Airlines
Deal found 5/11£427
Fri 5/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Sun 7/1219:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 4/11£460
Tue 23/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Mon 5/119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 3/11£463
Wed 24/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Mon 5/119:20ORD - MAN
2 stops58h 55mScandinavian Airlines
Deal found 3/11£466
Tue 18/1119:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Sun 23/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 4/11£468
Wed 17/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Wed 14/119:20ORD - MAN
2 stops58h 55mScandinavian Airlines
Deal found 5/11£475
Fri 14/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sat 13/1219:20ORD - MAN
2 stops42h 45mScandinavian Airlines
Deal found 4/11£486
Fri 5/1208:40MAN - ORD
1 stop15h 15mMultiple Airlines
Fri 12/1219:40ORD - MAN
1 stop16h 15mMultiple Airlines
Deal found 5/11£494
Tue 18/1112:30MAN - ORD
3 stops34h 15mMultiple Airlines
Sun 23/1119:20ORD - MAN
2 stops20h 55mMultiple Airlines
Deal found 4/11£498
Wed 10/1213:30MAN - MDW
1 stop16h 17mVirgin Atlantic
Sun 14/1209:34MDW - MAN
2 stops16h 21mVirgin Atlantic
Deal found 5/11£664
Fri 5/1213:25MAN - MDW
1 stop16h 22mDelta
Sun 7/1213:14MDW - MAN
2 stops14h 56mDelta
Deal found 4/11£673
Tue 18/1113:00MAN - MDW
2 stops16h 40mDelta
Sun 23/1113:15MDW - MAN
2 stops17h 30mDelta
Deal found 4/11£688

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 6 November 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

Fri 5/12

20:55-16:45

2 stops25h 50m

Chicago O'Hare Intl

Fri 12/12

19:20-08:40

2 stops31h 20m

£427

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/2

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Fri 13/2

19:20-19:30

2 stops18h 10m

£440

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 3/3

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Tue 10/3

10:10-09:30

2 stops18h 20m

£456

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Fri 13/2

19:20-19:30

2 stops18h 10m

£456

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 21/2

20:15-16:55

2 stops26h 40m

Chicago O'Hare Intl

Sat 28/2

19:20-19:45

2 stops18h 25m

£456

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 5/12

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Sun 7/12

19:20-18:35

1 stop17h 15m

£460

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 23/12

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 5/1

19:20-18:35

1 stop17h 15m

£463

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 14/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 20/2

19:20-18:35

1 stop17h 15m

£466

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 29/4

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Sat 16/5

19:15-18:50

1 stop17h 35m

£475

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 29/4

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Mon 11/5

19:15-08:55

1 stop31h 40m

£475

Flights are sorted by cheapest return flights first.

Deals found on 5/11

Showing 1-10 of 35 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 31 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 £147). Flying from York to Chicago in July is currently the most expensive (average of £614). 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 6 November 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.

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 6 November 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
672 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

6.9

Crew

8.1

Entertainment

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
672 reviews
Virgin Atlantic
7.5
Good
672 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

6.9

Crew

8.1

Entertainment

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
7.4
Good
1,560 reviews
Virgin Atlantic
7.5
Good
672 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

6.9

Crew

8.1

Entertainment

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
1,365 reviews
Virgin Atlantic
7.5
Good
672 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

6.9

Crew

8.1

Entertainment

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
7.1
Good
571 reviews
Virgin Atlantic
7.5
Good
672 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

6.9

Crew

8.1

Entertainment

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
7,496 reviews
Virgin Atlantic
7.5
Good
672 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

6.9

Crew

8.1

Entertainment

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 and Delta fly from York to Chicago in about 14h 39m. The time it takes to get you to your destination can typically vary by up to 11h 11m. 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 £147). Flying from York to Chicago in July is currently the most expensive (average of £614). 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 6 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest£379Average£466FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£384Average£639FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
IcelandairCheapest£425Average£548FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
British AirwaysCheapest£444Average£622FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Aer LingusCheapest£462Average£724FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
KLMCheapest£466Average£643FlexibilityNo cancel feeOn-time75%
Search KLM flights
FinnairCheapest£478Average£725FlexibilityNo cancel feeOn-time76%
Search Finnair flights
LufthansaCheapest£485Average£637FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Virgin AtlanticCheapest£495Average£632FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£513Average£647FlexibilityNo 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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