Find flights
When to book
Airlines
FAQs

Cheap flights from Sheffield to Chicago from £277

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
19 Feb — 26 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Sheffield to Chicago

Keep the following information in mind while searching for Sheffield to Chicago flight deals. Data was last updated 20 January 2026.

Round-trip from

£412

One-way from

£277

Popular in

July

Cheapest in

February

Average price

£500
Scandinavian Airlines
  • Scandinavian Airlines
  • 18/2-25/4
  • 2 total stops
  • 59h 10m total
  • Sheffield to Chicago
Search Deals
1/6
  • 1/6
  • 2 total stops
  • 29h 10m total
  • Sheffield to Chicago
Search Deals
Highest demand for flights based on searches. 16% 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 January 2026
Search Deals

Find flight deals from Sheffield to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Sheffield to Chicago
Explore the most affordable flight options available from Sheffield to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 January 2026.

Sat 7/212:30
MAN
-
ORD
2 stops35h 34m
Multiple Airlines
Sun 15/221:00
ORD
-
MAN
1 stop10h 25m
Multiple Airlines
Deal found 20/1£409
Wed 18/219:15
MAN
-
ORD
1 stop27h 30m
Scandinavian Airlines
Fri 24/419:15
ORD
-
MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 18/1£412
Mon 13/408:00
MAN
-
ORD
2 stops30h 25m
Multiple Airlines
Thu 16/419:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 18/1£412
Wed 4/210:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 8/219:10
ORD
-
MAN
1 stop17h 25m
Scandinavian Airlines
Deal found 19/1£413
Wed 4/311:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Wed 11/319:30
ORD
-
MAN
1 stop10h 30m
Icelandair
Deal found 18/1£417
Thu 22/1009:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 1/1119:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 18/1£421
Tue 14/419:10
MAN
-
ORD
1 stop27h 00m
Scandinavian Airlines
Sat 18/419:15
ORD
-
MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 18/1£424
Fri 17/420:25
MAN
-
ORD
2 stops25h 45m
Scandinavian Airlines
Fri 24/419:15
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 17/1£424
Wed 4/313:30
MAN
-
MDW
1 stop15h 01m
Virgin Atlantic
Wed 11/317:40
MDW
-
MAN
1 stop11h 50m
Virgin Atlantic
Deal found 18/1£500
Fri 30/113:25
MAN
-
MDW
1 stop14h 57m
Virgin Atlantic
Thu 5/212:46
MDW
-
MAN
1 stop15h 44m
Virgin Atlantic
Deal found 18/1£518
Thu 8/1013:00
MAN
-
MDW
1 stop14h 45m
Virgin Atlantic
Sun 11/1010:35
MDW
-
MAN
1 stop14h 40m
Virgin Atlantic
Deal found 18/1£520
Fri 30/113:25
MAN
-
MDW
1 stop14h 57m
KLM
Thu 5/213:26
MDW
-
MAN
2 stops12h 54m
KLM
Deal found 18/1£524

Cheapflights Fare Finder

 
Customise your flight search to find flights from Sheffield 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 20 January 2026.
Use the filters below to find and compare flights from Sheffield to Chicago that are best for you.

Fly from

Sheffield

Fly to

Chicago

Route

Depart

Return

Price

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 19/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 20/4

19:15-08:55

1 stop31h 40m

£412

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 4/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sun 8/2

19:10-18:35

1 stop17h 25m

£413

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 17/4

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Sat 25/4

19:15-08:55

1 stop31h 40m

£427

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 22/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Sat 25/4

19:15-08:55

1 stop31h 40m

£427

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 19/4

19:30-16:10

1 stop26h 40m

Chicago O'Hare Intl

Fri 24/4

19:15-11:45

2 stops34h 30m

£427

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 22/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 20/4

19:15-08:55

1 stop31h 40m

£427

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 17/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Fri 24/4

19:15-08:55

1 stop31h 40m

£427

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 9/2

19:20-18:35

1 stop17h 15m

£428

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

20:55-16:45

2 stops25h 50m

Chicago O'Hare Intl

Wed 11/2

19:20-18:35

1 stop17h 15m

£435

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 30/1

13:25-22:22

1 stop14h 57m

Chicago Midway

Thu 5/2

12:46-10:30

1 stop15h 44m

£518

Flights are sorted by cheapest return flights first.

Deals found on 18/1

Showing 1-10 of 34 results
1
2
3
4

Best time to book a flight from Sheffield to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sheffield 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 Sheffield to Chicago

How far ahead should I book a flight from Sheffield to Chicago?

Use this chart to determine the optimal time to book a return flight from Sheffield to Chicago. Price data was last updated on 16 January 2026.

To ensure you get the cheapest price possible for a flight from Sheffield to Chicago, you should look to book at least 59 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, January is the cheapest month in which you can book a flight from Sheffield to Chicago (average of £38). Flying from Sheffield to Chicago in July is currently the most expensive (average of £600). 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 20 January 2026.
Get a feel of what it's like to fly with Virgin Atlantic, Scandinavian Airlines, andAer Lingus from Sheffield to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Overall

7.5

Boarding

7.7

Entertainment

7.6

Comfort

7.3

Crew

8.2

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
678 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Overall

7.5

Boarding

7.7

Entertainment

7.6

Comfort

7.3

Crew

8.2

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
1,655 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Overall

7.5

Boarding

7.7

Entertainment

7.6

Comfort

7.3

Crew

8.2

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
1,437 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Overall

7.5

Boarding

7.7

Entertainment

7.6

Comfort

7.3

Crew

8.2

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
598 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Overall

7.5

Boarding

7.7

Entertainment

7.6

Comfort

7.3

Crew

8.2

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
7,691 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Overall

7.5

Boarding

7.7

Entertainment

7.6

Comfort

7.3

Crew

8.2

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 Sheffield 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 Sheffield to Chicago?

    Scandinavian Airlines, Virgin Atlantic, and Delta can get you from Sheffield to Chicago in just under 12h 35m. Your travel time can differ by up to 6h 11m. There are 3812 mi between Sheffield and Chicago. Both multi-stop and direct flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with Scandinavian Airlines, which is currently one of the cheapest options available, starting at £318. Icelandair flights start at £344 while deals on Aer Lingus start at £470 one-way.

  • Can I find deals for flights from Sheffield to Chicago that include hotel bookings?

    Yes. In addition to deals on Sheffield to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Sheffield to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sheffield to Chicago.

  • Can I find deals for business class flights from Sheffield to Chicago?

    Yes. Cheapflights offers flight deals from Sheffield 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 Sheffield to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Sheffield to Chicago (average of £38). Flying from Sheffield to Chicago in July is currently the most expensive (average of £600). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Sheffield to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Heathrow to O'Hare Intl flights
Gatwick to O'Hare Intl flights
Heathrow to Midway flights
London City to O'Hare Intl flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Manchester to O'Hare Intl flights
Heathrow to St. Louis flights
Edinburgh to Midway flights
Manchester to Midway flights
Gatwick to Midway flights
Birmingham to O'Hare Intl flights
Gatwick to St. Louis flights
Newcastle upon Tyne to O'Hare Intl flights
London City to St. Louis flights
Stansted to St. Louis flights
Southampton to O'Hare Intl flights
Birmingham to Midway flights
Norwich to O'Hare Intl flights
Luton to St. Louis flights
Leeds to O'Hare Intl flights
Bristol to O'Hare Intl flights
London City to Midway flights
Newcastle upon Tyne to Midway flights
Liverpool to O'Hare Intl flights
Heathrow to Champaign flights
Bristol to Midway flights
Manchester to Peoria flights
Edinburgh to Moline flights
Manchester to St. Louis flights
Gatwick to Champaign flights
Birmingham to St. Louis flights
Manchester to Moline flights
Heathrow to Peoria flights
Southend to O'Hare Intl flights
Exeter to O'Hare Intl flights
Leeds to Midway flights
Edinburgh to St. Louis flights
Heathrow to Evansville flights
Grimsby to O'Hare Intl flights
Newquay to O'Hare Intl flights
Heathrow to Moline flights
Liverpool to St. Louis flights
Darlington to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Darlington to Midway flights
Grimsby to St. Louis flights
Heathrow to Springfield flights
Southampton to Midway flights

Top 10 airlines flying from Sheffield to Chicago

Discover the top 10 airlines that operate flights from Sheffield 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 20 January 2026.
AirlineCheapestAverageFlexibilityOn-time
LufthansaCheapest£287Average£687FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Scandinavian AirlinesCheapest£377Average£468FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£412Average£548FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£453Average£668FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
British AirwaysCheapest£453Average£626FlexibilityNo cancel feeOn-time70%
Search British Airways flights
FinnairCheapest£464Average£781FlexibilityNo cancel feeOn-time76%
Search Finnair flights
KLMCheapest£476Average£673FlexibilityNo cancel feeOn-time75%
Search KLM flights
Virgin AtlanticCheapest£481Average£644FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£498Average£629FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air FranceCheapest£500Average£673FlexibilityNo cancel feeOn-time77%
Search Air France 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 Sheffield to Chicago?

Cheapflights makes it easy to find Sheffield to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Sheffield to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Sheffield.

Can Cheapflights find flights from Sheffield to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Sheffield to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Sheffield to Chicago become cheaper?

Of course! You can now track prices for flights from Sheffield to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.