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Cheap flights from Sheffield to Chicago from £284

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
23 May — 30 May1
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 23 April 2026.

Thu 17/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Wed 7/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 21/4£501
Thu 17/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Thu 8/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 21/4£502
Thu 17/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Sun 27/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 21/4£506
Thu 17/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Mon 28/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 21/4£507
Tue 19/513:40
MAN
-
ORD
2 stops34h 35m
Multiple Airlines
Tue 26/519:25
ORD
-
MAN
2 stops19h 35m
Multiple Airlines
Deal found 19/4£508
Sat 5/907:45
MAN
-
ORD
2 stops16h 05m
Multiple Airlines
Tue 22/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 21/4£520
Thu 3/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Tue 8/921:00
ORD
-
MAN
1 stop10h 55m
Multiple Airlines
Deal found 20/4£520
Thu 17/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Tue 6/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 21/4£524
Wed 28/1019:15
MAN
-
ORD
1 stop27h 30m
Scandinavian Airlines
Tue 3/1119:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 21/4£540
Tue 19/507:30
MAN
-
MDW
2 stops32h 15m
Multiple Airlines
Tue 26/515:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 19/4£658
Mon 21/920:50
MAN
-
MDW
2 stops27h 41m
Virgin Atlantic
Mon 28/913:00
MDW
-
MAN
2 stops19h 00m
Virgin Atlantic
Deal found 20/4£696
Mon 21/913:00
MAN
-
MDW
1 stop14h 46m
Air France
Mon 28/917:59
MDW
-
MAN
2 stops14h 01m
Air France
Deal found 20/4£704

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 23 April 2026.

Round-trip from

£501

One-way from

£284

Popular in

July

Cheapest in

February

Average price

£554
Icelandair
  • Icelandair
  • 17/9-7/10
  • 3 total stops
  • 27h 10m total
  • Sheffield to Chicago
Search Deals
15/9
  • 15/9
  • 2 total stops
  • 34h 00m 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 (£12 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 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 23 April 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

Cheapest return flight

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 15/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Tue 20/10

19:15-08:55

1 stop31h 40m

£621

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 2/6

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Tue 9/6

10:29-18:30

2 stops26h 01m

£664
Fastest return journey

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 9/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Wed 14/10

13:05-07:15

1 stop12h 10m

£759

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-18:31

2 stops18h 36m

Chicago Midway

Wed 23/9

10:35-07:15

1 stop14h 40m

£763

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 16/7

17:55-16:00

1 stop28h 05m

Chicago O'Hare Intl

Wed 29/7

16:40-17:05

1 stop18h 25m

£769

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 24/6

23:30-09:40

1 stop16h 10m

Chicago O'Hare Intl

Thu 2/7

20:10-12:05

1 stop33h 55m

£791

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 15/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Tue 20/10

12:30-10:00

2 stops15h 30m

£807

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 2/6

05:55-20:05

2 stops20h 10m

Chicago O'Hare Intl

Tue 9/6

05:00-06:30

2 stops19h 30m

£823

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 30/6

15:00-21:48

1 stop12h 48m

Chicago O'Hare Intl

Tue 7/7

15:55-14:00

2 stops16h 05m

£827

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 16/6

05:55-19:31

2 stops19h 36m

Chicago O'Hare Intl

Wed 22/7

12:27-10:05

2 stops15h 38m

£827

Flights are sorted by cheapest return flights first.

Deals found on 18/4

Showing 1-10 of 39 resultsSorted by cheapest first
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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 17 April 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.

How much does it cost for a return flight from Sheffield 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 23 April 2026.
Get a feel of what it's like to fly with Virgin Atlantic,Aer Lingus, andScandinavian Airlines 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
687 reviews
Check prices

Food

6.9

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.5

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
687 reviews
Virgin Atlantic
7.5
Good
687 reviews
Check prices

Food

6.9

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.5

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
7.3
Good
1,521 reviews
Virgin Atlantic
7.5
Good
687 reviews
Check prices

Food

6.9

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.5

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
1,756 reviews
Virgin Atlantic
7.5
Good
687 reviews
Check prices

Food

6.9

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.5

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
7.0
Good
639 reviews
Virgin Atlantic
7.5
Good
687 reviews
Check prices

Food

6.9

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.5

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
7,906 reviews
Virgin Atlantic
7.5
Good
687 reviews
Check prices

Food

6.9

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.5

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 TAP AIR PORTUGAL can get you from Sheffield to Chicago in just under 12h 35m. Your travel time can differ by up to 15h 30m. There are 3812 mi between Sheffield and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • 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.

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 23 April 2026.
AirlineCheapestAverageFlexibilityOn-time
RyanairCheapest£37Average£48FlexibilityNo cancel feeOn-timeN/A
Search Ryanair flights
Scandinavian AirlinesCheapest£376Average£449FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£408Average£567FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£461Average£695FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
FinnairCheapest£461Average£800FlexibilityNo cancel feeOn-time76%
Search Finnair flights
British AirwaysCheapest£467Average£618FlexibilityNo cancel feeOn-time70%
Search British Airways flights
KLMCheapest£477Average£689FlexibilityNo cancel feeOn-time75%
Search KLM flights
LufthansaCheapest£478Average£702FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Virgin AtlanticCheapest£494Average£647FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£498Average£648FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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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.

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

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