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Cheap flights from Sheffield to Chicago from £248

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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
12 fev — 19 fev1
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 13 janeiro 2026.

Round-trip from

£395

One-way from

£248

Popular in

July

Cheapest in

February

Average price

£499
Scandinavian Airlines
  • Scandinavian Airlines
  • 4/2-8/2
  • 2 total stops
  • 44h 55m total
  • Sheffield to Chicago
Search Deals
21/4
  • 21/4
  • 2 total stops
  • 47h 46m total
  • Sheffield to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£80 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 13 janeiro 2026.

seg 12/1020:25
MAN
-
ORD
2 stops25h 45m
Scandinavian Airlines
sex 16/1019:15
ORD
-
MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 11/1£393
qua 4/210:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
dom 8/219:10
ORD
-
MAN
1 stop32h 20m
Scandinavian Airlines
Deal found 10/1£395
qui 22/1009:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
sáb 31/1020:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 11/1£397
dom 11/1019:30
MAN
-
ORD
1 stop26h 40m
Scandinavian Airlines
ter 3/1119:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 12/1£399
seg 9/310:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
dom 15/320:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 11/1£400
qua 18/311:55
MAN
-
ORD
1 stop11h 25m
Icelandair
ter 7/419:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 12/1£404
qui 5/213:55
MAN
-
ORD
2 stops32h 50m
Scandinavian Airlines
sex 20/219:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 12/1£407
sáb 17/113:30
MAN
-
MDW
1 stop14h 37m
Virgin Atlantic
sáb 24/116:30
MDW
-
MAN
1 stop12h 00m
Virgin Atlantic
Deal found 9/1£500
qua 25/213:00
MAN
-
MDW
1 stop15h 31m
Virgin Atlantic
seg 9/313:10
MDW
-
MAN
2 stops13h 45m
Virgin Atlantic
Deal found 12/1£521
sex 23/113:25
MAN
-
MDW
1 stop14h 57m
Delta
seg 26/113:26
MDW
-
MAN
2 stops14h 44m
Delta
Deal found 12/1£524
ter 24/213:30
MAN
-
MDW
1 stop15h 03m
Delta
ter 3/318:20
MDW
-
MAN
2 stops15h 45m
Delta
Deal found 10/1£525
dom 1/205:50
MAN
-
MDW
2 stops18h 46m
Delta
dom 8/213:26
MDW
-
MAN
2 stops14h 44m
Delta
Deal found 12/1£525

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 13 janeiro 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

qua 4/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

dom 8/2

19:10-20:05

2 stops18h 55m

£398

ManchesterChicago

MAN - ORD

MANORD

Manchester

sex 6/2

20:55-16:45

2 stops25h 50m

Chicago O'Hare Intl

qua 11/2

19:20-18:35

1 stop17h 15m

£411

ManchesterChicago

MAN - ORD

MANORD

Manchester

dom 1/2

10:10-16:55

1 stop12h 45m

Chicago O'Hare Intl

dom 8/2

19:10-18:35

1 stop17h 25m

£416

ManchesterChicago

MAN - ORD

MANORD

Manchester

qui 9/4

21:10-16:10

2 stops25h 00m

Chicago O'Hare Intl

seg 13/4

19:15-19:10

2 stops17h 55m

£431

ManchesterChicago

MAN - ORD

MANORD

Manchester

sex 22/5

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

sex 29/5

19:15-08:55

1 stop31h 40m

£449

ManchesterChicago

MAN - ORD

MANORD

Manchester

sex 22/5

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

dom 31/5

19:15-12:05

2 stops34h 50m

£461

ManchesterChicago

MAN - ORD

MANORD

Manchester

sáb 16/5

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

sáb 30/5

18:10-08:55

2 stops56h 45m

£492

ManchesterChicago

MAN - ORD

MANORD

Manchester

seg 2/2

06:45-08:18

3 stops31h 33m

Chicago O'Hare Intl

dom 8/2

18:30-10:45

1 stop10h 15m

£494

ManchesterChicago

MAN - MDW

MANMDW

Manchester

qui 12/2

13:30-22:31

1 stop15h 01m

Chicago Midway

qui 19/2

12:45-10:30

1 stop15h 45m

£511

ManchesterChicago

MAN - MDW

MANMDW

Manchester

seg 2/2

09:00-17:29

1 stop14h 29m

Chicago Midway

dom 8/2

13:26-10:10

2 stops14h 44m

£524

Flights are sorted by cheapest return flights first.

Deals found on 11/1

Showing 1-10 of 35 results
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2
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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 9 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 £596). 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 13 janeiro 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

Entertainment

7.6

Overall

7.5

Comfort

7.3

Boarding

7.7

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

Entertainment

7.6

Overall

7.5

Comfort

7.3

Boarding

7.7

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
1,646 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Entertainment

7.6

Overall

7.5

Comfort

7.3

Boarding

7.7

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
1,435 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Entertainment

7.6

Overall

7.5

Comfort

7.3

Boarding

7.7

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
595 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Entertainment

7.6

Overall

7.5

Comfort

7.3

Boarding

7.7

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
7,665 reviews
Virgin Atlantic
7.5
Good
678 reviews
Check prices

Food

6.9

Entertainment

7.6

Overall

7.5

Comfort

7.3

Boarding

7.7

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 2h 26m. 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 £317. Icelandair flights start at £355 while deals on Aer Lingus start at £448 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 £596). 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 Sheffield 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 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 13 janeiro 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest£375Average£456FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£411Average£541FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£448Average£664FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
British AirwaysCheapest£449Average£623FlexibilityNo cancel feeOn-time70%
Search British Airways flights
FinnairCheapest£463Average£754FlexibilityNo cancel feeOn-time76%
Search Finnair flights
LufthansaCheapest£470Average£617FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
KLMCheapest£474Average£668FlexibilityNo cancel feeOn-time75%
Search KLM flights
Virgin AtlanticCheapest£480Average£637FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£497Average£627FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air FranceCheapest£499Average£671FlexibilityNo 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.

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