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Cheap flights from Sheffield to Chicago from £256

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
30 Mar — 6 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap 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 28 February 2026.

Mon 13/407:45
MAN
-
ORD
3 stops33h 08m
Multiple Airlines
Mon 27/419:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 25/2£411
Thu 16/422:55
MAN
-
ORD
2 stops25h 20m
Multiple Airlines
Mon 27/419:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 25/2£417
Thu 16/421:10
MAN
-
ORD
2 stops25h 00m
Scandinavian Airlines
Mon 27/419:15
ORD
-
MAN
2 stops34h 50m
Scandinavian Airlines
Deal found 25/2£419
Tue 14/419:40
MAN
-
ORD
2 stops26h 20m
Multiple Airlines
Tue 21/419:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 28/2£421
Wed 4/1110:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sat 7/1119:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 25/2£439
Mon 4/507:45
MAN
-
ORD
2 stops17h 40m
Multiple Airlines
Fri 8/522:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 25/2£451
Thu 29/1019:15
MAN
-
ORD
1 stop27h 30m
Scandinavian Airlines
Sat 7/1119:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 27/2£459
Thu 30/406:00
MAN
-
ORD
2 stops17h 50m
Multiple Airlines
Mon 18/522:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 27/2£460
Thu 12/310:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Mon 23/320:20
ORD
-
MAN
2 stops34h 55m
Scandinavian Airlines
Deal found 27/2£461
Tue 14/405:55
MAN
-
MDW
2 stops18h 03m
Delta
Tue 21/410:41
MDW
-
MAN
2 stops15h 39m
Delta
Deal found 28/2£630
Mon 13/405:55
MAN
-
MDW
2 stops18h 41m
Delta
Mon 27/409:27
MDW
-
MAN
2 stops16h 48m
Delta
Deal found 25/2£631
Mon 13/405:55
MAN
-
MDW
2 stops18h 41m
Virgin Atlantic
Mon 27/413:24
MDW
-
MAN
2 stops12h 51m
Virgin Atlantic
Deal found 27/2£632

Find flight deals from Sheffield to Chicago

Keep the following information in mind while searching for Sheffield to Chicago flight deals. Data was last updated 28 February 2026.

Round-trip from

£411

One-way from

£256

Popular in

July

Cheapest in

February

Average price

£481
Icelandair
  • Icelandair
  • 13/4-27/4
  • 4 total stops
  • 43h 23m total
  • Sheffield to Chicago
Search Deals
9/4
  • 9/4
  • 3 total stops
  • 24h 22m total
  • Sheffield to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£76 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 28 February 2026.
Use the filters below to find and compare flights from Sheffield to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 12/3

13:55-17:55

2 stops33h 00m

Chicago O'Hare Intl

Mon 23/3

20:20-12:15

2 stops34h 55m

£508

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 5/4

21:35-18:15

2 stops26h 40m

Chicago O'Hare Intl

Tue 28/4

19:25-11:40

1 stop10h 15m

£583

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 14/4

05:55-17:58

2 stops18h 03m

Chicago Midway

Tue 21/4

10:41-08:20

2 stops15h 39m

£630

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 13/4

05:55-18:36

2 stops18h 41m

Chicago Midway

Mon 27/4

10:41-08:50

1 stop16h 09m

£631

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 13/4

05:55-18:36

2 stops18h 41m

Chicago Midway

Mon 27/4

13:24-08:15

2 stops12h 51m

£632

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 13/3

13:00-21:05

1 stop13h 05m

Chicago O'Hare Intl

Mon 16/3

14:35-12:20

2 stops16h 45m

£676

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 11/4

06:05-23:43

2 stops23h 38m

Chicago O'Hare Intl

Sat 18/4

17:45-10:25

2 stops34h 40m

£683

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 5/4

11:10-11:00

1 stop29h 50m

Chicago O'Hare Intl

Tue 28/4

16:05-10:40

1 stop12h 35m

£693

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 4/5

10:35-18:15

1 stop13h 40m

Chicago O'Hare Intl

Sat 23/5

15:10-10:25

1 stop13h 15m

£706

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 25/3

06:00-17:54

2 stops16h 54m

Chicago Midway

Wed 1/4

10:45-07:15

1 stop14h 30m

£755

Flights are sorted by cheapest return flights first.

Deals found on 26/2

Showing 1-10 of 31 resultsSorted by cheapest first
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 20 February 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 £67). 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 28 February 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
680 reviews
Check prices

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Boarding

7.7

Overall

7.5

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
680 reviews
Virgin Atlantic
7.5
Good
680 reviews
Check prices

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Boarding

7.7

Overall

7.5

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
1,700 reviews
Virgin Atlantic
7.5
Good
680 reviews
Check prices

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Boarding

7.7

Overall

7.5

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
1,464 reviews
Virgin Atlantic
7.5
Good
680 reviews
Check prices

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Boarding

7.7

Overall

7.5

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
617 reviews
Virgin Atlantic
7.5
Good
680 reviews
Check prices

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Boarding

7.7

Overall

7.5

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
7,772 reviews
Virgin Atlantic
7.5
Good
680 reviews
Check prices

Crew

8.2

Food

6.9

Comfort

7.3

Entertainment

7.6

Boarding

7.7

Overall

7.5

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, Delta, and Virgin Atlantic can get you from Sheffield to Chicago in just under 18h 03m. Your travel time can differ by up to 14h 57m. There are 3816 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 £316. Icelandair flights start at £394 while deals on Aer Lingus start at £473 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 £67). 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

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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 28 February 2026.
AirlineCheapestAverageFlexibilityOn-time
LufthansaCheapest£286Average£683FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Scandinavian AirlinesCheapest£377Average£450FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£409Average£544FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
FinnairCheapest£462Average£801FlexibilityNo cancel feeOn-time76%
Search Finnair flights
British AirwaysCheapest£464Average£617FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Aer LingusCheapest£480Average£688FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
KLMCheapest£482Average£678FlexibilityNo cancel feeOn-time75%
Search KLM flights
Virgin AtlanticCheapest£492Average£639FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£495Average£625FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air FranceCheapest£497Average£669FlexibilityNo 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.

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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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