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 22/10. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
3 Sep — 10 Sep1
Return
1 adult
Economy
Cheapflights Tip: The best prices from York to Chicago are usually found in February or January, booked 77 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 29 August 2025.
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 29 August 2025.
Wed 24/912:40MAN - ORD
1 stop14h 35mIcelandair
Tue 7/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£459
Wed 10/913:05MAN - ORD
1 stop14h 10mIcelandair
Wed 24/922:15ORD - MAN
1 stop31h 25mIcelandair
Deal found 28/8£463
Wed 1/1012:40MAN - ORD
1 stop11h 35mIcelandair
Sun 5/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 28/8£472
Wed 17/913:05MAN - ORD
1 stop11h 10mIcelandair
Mon 6/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£475
Wed 19/1111:55MAN - ORD
1 stop11h 25mIcelandair
Tue 2/1218:30ORD - MAN
1 stop10h 15mIcelandair
Deal found 26/8£484
Mon 17/1111:55MAN - ORD
1 stop11h 25mIcelandair
Tue 2/1218:30ORD - MAN
1 stop10h 15mIcelandair
Deal found 26/8£486
Fri 24/1019:10MAN - ORD
1 stop27h 00mScandinavian Airlines
Wed 29/1023:10ORD - MAN
1 stop14h 25mScandinavian Airlines
Deal found 27/8£489
Sun 12/1012:40MAN - ORD
1 stop14h 35mIcelandair
Wed 15/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£491
Wed 1/1009:20MAN - ORD
1 stop11h 30mBritish Airways
Wed 15/1021:15ORD - MAN
1 stop12h 20mBritish Airways
Deal found 27/8£494
Sat 11/1010:55MAN - ORD
2 stops33h 15mMultiple Airlines
Sat 18/1017:10ORD - MAN
2 stops20h 20mMultiple Airlines
Deal found 27/8£494
Wed 1/1014:00MAN - ORD
2 stops28h 41mFinnair
Mon 6/1022:35ORD - MAN
1 stop13h 10mFinnair
Deal found 28/8£496
Wed 1/1011:55MAN - MDW
1 stop15h 41mVirgin Atlantic
Mon 6/1013:08MDW - MAN
2 stops15h 12mVirgin Atlantic
Deal found 28/8£513
Best flights from York to Chicago
Discover carefully curated flight deals from York to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 29 August 2025.
Wed 10/913:05MAN - ORD
1 stop14h 10mIcelandair
Wed 24/922:15ORD - MAN
1 stop31h 25mIcelandair
Deal found 28/8£463
Wed 1/1011:55MAN - MDW
1 stop15h 41mVirgin Atlantic
Mon 6/1013:08MDW - MAN
2 stops15h 12mVirgin Atlantic
Deal found 28/8£513
Wed 1/1008:55MAN - MDW
2 stops15h 40mDelta
Mon 6/1018:23MDW - MAN
2 stops13h 02mDelta
Deal found 28/8£519
Wed 1/1012:40MAN - ORD
1 stop11h 35mIcelandair
Sun 5/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 28/8£472
Wed 17/913:05MAN - ORD
1 stop11h 10mIcelandair
Thu 2/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£475
Fri 7/1113:25MAN - MDW
1 stop14h 49mVirgin Atlantic
Wed 12/1113:14MDW - MAN
2 stops14h 56mVirgin Atlantic
Deal found 27/8£525
Wed 19/1113:30MAN - MDW
1 stop16h 02mDelta
Tue 2/1214:00MDW - MAN
2 stops14h 10mDelta
Deal found 26/8£540
Wed 17/913:05MAN - ORD
1 stop11h 10mIcelandair
Mon 6/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£475
Fri 7/1113:25MAN - MDW
1 stop14h 49mDelta
Wed 12/1113:47MDW - MAN
2 stops14h 23mDelta
Deal found 28/8£540
Wed 24/912:40MAN - ORD
1 stop11h 35mIcelandair
Mon 6/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£475
Tue 23/912:35MAN - MDW
1 stop15h 01mDelta
Tue 7/1018:23MDW - MAN
2 stops13h 02mDelta
Deal found 27/8£548
Wed 19/1111:55MAN - ORD
1 stop11h 25mIcelandair
Tue 9/1218:30ORD - MAN
1 stop10h 15mIcelandair
Deal found 26/8£486
Last-minute flights from York to Chicago
Discover last-minute flight deals from York to Chicago. Data last updated 29 August 2025 and is based on user searches.
Sun 7/908:35MAN - ORD
1 stop11h 25mMultiple Airlines
Thu 11/921:15ORD - MAN
1 stop19h 35mMultiple Airlines
Deal found 28/8£502
Mon 8/905:55MAN - ORD
1 stop14h 45mVirgin Atlantic
Thu 2/1016:15ORD - MAN
1 stop18h 30mVirgin Atlantic
Deal found 28/8£500
Mon 8/917:30MAN - ORD
1 stop26h 40mVirgin Atlantic
Mon 6/1017:10ORD - MAN
1 stop12h 00mVirgin Atlantic
Deal found 27/8£510
Mon 8/905:55MAN - ORD
1 stop14h 45mDelta
Thu 2/1018:28ORD - MAN
2 stops16h 27mDelta
Deal found 27/8£514
Wed 10/913:05MAN - ORD
1 stop14h 10mIcelandair
Wed 24/922:15ORD - MAN
1 stop31h 25mIcelandair
Deal found 28/8£463
Wed 10/906:05MAN - ORD
1 stop12h 00mUnited Airlines
Wed 24/908:50ORD - MAN
2 stops19h 30mUnited Airlines
Deal found 28/8£514
Tue 16/908:10MAN - ORD
1 stop11h 50mAer Lingus
Tue 9/1219:40ORD - MAN
1 stop11h 45mAer Lingus
Deal found 26/8£486
Wed 17/913:05MAN - ORD
1 stop11h 10mIcelandair
Mon 6/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£475
Wed 17/913:05MAN - ORD
1 stop11h 10mIcelandair
Fri 3/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£500
Fri 19/913:05MAN - ORD
1 stop11h 10mIcelandair
Sun 5/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£508
Sun 21/919:50MAN - ORD
2 stops25h 55mBritish Airways
Mon 6/1022:35ORD - MAN
1 stop13h 10mBritish Airways
Deal found 27/8£517
Wed 24/912:40MAN - ORD
1 stop14h 35mIcelandair
Tue 7/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£459
One-way flights from York to Chicago
Search for one-way flight options from York to Chicago. Find affordable one-way fares based on user searches. Data last updated 29 August 2025.
Wed 22/1017:50MAN - ORD
2 stops24h 45mMultiple Airlines
Deal found 28/8£243
Wed 15/1020:25MAN - ORD
2 stops22h 10mMultiple Airlines
Deal found 28/8£248
Sat 15/1122:15MAN - ORD
2 stops22h 45mMultiple Airlines
Deal found 29/8£250
Tue 14/1020:40MAN - ORD
3 stops45h 55mMultiple Airlines
Deal found 28/8£261
Wed 22/1018:55MAN - MDW
3 stops34h 30mMultiple Airlines
Deal found 28/8£293
Mon 15/907:45MAN - ORD
2 stops39h 06mMultiple Airlines
Deal found 27/8£306
Sat 20/917:15MAN - ORD
3 stops46h 03mMultiple Airlines
Deal found 28/8£318
Mon 15/921:45MAN - MDW
3 stops48h 13mMultiple Airlines
Deal found 27/8£319
Sat 20/920:15MAN - MDW
3 stops41h 08mMultiple Airlines
Deal found 28/8£330
Wed 15/1015:15MAN - MDW
3 stops38h 10mMultiple Airlines
Deal found 28/8£334
Sun 7/920:00MAN - MDW
3 stops49h 58mMultiple Airlines
Deal found 28/8£363
Tue 14/1009:05MAN - MDW
3 stops20h 20mMultiple Airlines
Deal found 28/8£392
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 29 August 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
Wed 10/9
13:05-21:15
1 stop14h 10m
Chicago O'Hare Intl
Wed 24/9
22:15-11:40
1 stop31h 25m
£463
ManchesterChicago
MAN - ORD
MANORD
Manchester
Wed 1/10
12:40-18:15
1 stop11h 35m
Chicago O'Hare Intl
Sun 5/10
19:25-11:40
1 stop10h 15m
£472
ManchesterChicago
MAN - ORD
MANORD
Manchester
Wed 17/9
13:05-18:15
1 stop11h 10m
Chicago O'Hare Intl
Thu 2/10
19:25-11:40
1 stop10h 15m
£475
ManchesterChicago
MAN - ORD
MANORD
Manchester
Wed 17/9
13:05-18:15
1 stop11h 10m
Chicago O'Hare Intl
Mon 6/10
19:25-11:40
1 stop10h 15m
£475
ManchesterChicago
MAN - ORD
MANORD
Manchester
Wed 24/9
12:40-18:15
1 stop11h 35m
Chicago O'Hare Intl
Mon 6/10
19:25-11:40
1 stop10h 15m
£475
ManchesterChicago
MAN - ORD
MANORD
Manchester
Wed 19/11
11:55-17:20
1 stop11h 25m
Chicago O'Hare Intl
Tue 9/12
18:30-10:45
1 stop10h 15m
£486
ManchesterChicago
MAN - ORD
MANORD
Manchester
Tue 18/11
11:55-17:20
1 stop11h 25m
Chicago O'Hare Intl
Tue 9/12
18:30-10:45
1 stop10h 15m
£486
ManchesterChicago
MAN - ORD
MANORD
Manchester
Mon 17/11
11:55-17:20
1 stop11h 25m
Chicago O'Hare Intl
Tue 9/12
18:30-10:45
1 stop10h 15m
£486
ManchesterChicago
MAN - ORD
MANORD
Manchester
Mon 17/11
11:55-17:20
1 stop11h 25m
Chicago O'Hare Intl
Tue 2/12
18:30-10:45
1 stop10h 15m
£486
ManchesterChicago
MAN - ORD
MANORD
Manchester
Wed 22/10
12:40-18:15
1 stop11h 35m
Chicago O'Hare Intl
Sun 26/10
19:30-10:45
1 stop10h 15m
£491
Flights are sorted by cheapest return flights first.
Deals found on 28/8
Showing 1-10 of 28 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 22 August 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 77 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 £595). Flying from York to Chicago in July is currently the most expensive (average of £843). 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 29 August 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from York to Chicago as you normally would.
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 29 August 2025.
Read through reviews of airlines operating flights from York to Chicago, such as Scandinavian Airlines, Virgin Atlantic, andAer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
When I got to Copenhagen, my two suitcases were missing from Monday 1030. I got them back Friday after five in the afternoon. My flight from Copenhagen to Seattle did not make the connection from Seattle to Honolulu
When I got to Copenhagen, my two suitcases were missing from Monday 1030. I got them back Friday after five in the afternoon. My flight from Copenhagen to Seattle did not make the connection from Seattle to Honolulu
When I got to Copenhagen, my two suitcases were missing from Monday 1030. I got them back Friday after five in the afternoon. My flight from Copenhagen to Seattle did not make the connection from Seattle to Honolulu
When I got to Copenhagen, my two suitcases were missing from Monday 1030. I got them back Friday after five in the afternoon. My flight from Copenhagen to Seattle did not make the connection from Seattle to Honolulu
When I got to Copenhagen, my two suitcases were missing from Monday 1030. I got them back Friday after five in the afternoon. My flight from Copenhagen to Seattle did not make the connection from Seattle to Honolulu
When I got to Copenhagen, my two suitcases were missing from Monday 1030. I got them back Friday after five in the afternoon. My flight from Copenhagen to Seattle did not make the connection from Seattle to Honolulu
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 Icelandair, Virgin Atlantic, and Delta fly from York to Chicago in about 14h 10m. The time it takes to get you to your destination can typically vary by up to 1h 31m. York and Chicago are separated by a distance of 3812 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 £595). Flying from York to Chicago in July is currently the most expensive (average of £843). 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.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 29 August 2025.
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 29 August 2025.
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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