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Cheap flights from Sheffield to Chicago from £281

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 16/10. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
8 Sep — 15 Sep1
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 9 August 2026.

Tue 15/908:10 -
1 stop11h 50m
Tue 22/915:45 -
1 stop9h 55m
Deal found 5/8£505
Mon 23/1107:45 -
2 stops15h 35m
Thu 3/1218:30 -
1 stop10h 15m
Deal found 6/8£508
Tue 22/913:35 -
2 stops37h 45m
Tue 29/919:25 -
1 stop10h 15m
Deal found 7/8£510
Thu 17/908:10 -
1 stop11h 50m
Tue 22/915:45 -
1 stop13h 15m
Deal found 6/8£510
Thu 3/919:20 -
2 stops32h 05m
Tue 8/919:25 -
2 stops16h 00m
Deal found 5/8£512
Thu 26/1111:55 -
1 stop11h 25m
Tue 1/1218:30 -
1 stop10h 15m
Deal found 6/8£513
Mon 12/1012:05 -
1 stop13h 10m
Mon 26/1016:55 -
1 stop11h 35m
Deal found 5/8£517
Mon 23/1108:05 -
1 stop16h 20m
Thu 3/1215:55 -
1 stop11h 35m
Deal found 6/8£518
Sun 25/1010:35 -
2 stops37h 15m
Sun 1/1118:30 -
1 stop10h 15m
Deal found 6/8£519
Thu 12/1111:55 -
1 stop11h 25m
Fri 27/1118:30 -
1 stop10h 15m
Deal found 6/8£521
Thu 17/917:55 -
1 stop28h 05m
Thu 24/918:00 -
1 stop34h 05m
Deal found 5/8£522
Tue 10/1112:40 -
1 stop16h 16m
Tue 17/1113:22 -
2 stops14h 43m
Deal found 5/8£697

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 9 August 2026.

Round-trip from

£505

One-way from

£281

Popular in

July

Cheapest in

February

Average price

£750
Aer Lingus
  • Aer Lingus
  • 15/9-22/9
  • 2 total stops
  • 21h 45m total
  • Sheffield to Chicago
Search Deals
16/10
  • 16/10
  • 3 total stops
  • 37h 15m total
  • Sheffield to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (£90 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£13 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 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 9 August 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 Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Thu 12/11

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Fri 27/11

19:15-08:40

2 stops31h 25m

£541

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Wed 7/10

13:05-21:25

1 stop14h 20m

Chicago O'Hare Intl

Wed 14/10

22:25-11:40

1 stop31h 15m

£559

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Mon 28/9

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Tue 6/10

19:15-09:40

2 stops32h 25m

£575

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Mon 5/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Sun 18/10

19:15-18:30

1 stop17h 15m

£583
Fastest return journey

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Wed 25/11

11:55-17:20

1 stop11h 25m

Chicago O'Hare Intl

Sun 29/11

18:30-10:45

1 stop10h 15m

£602

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Wed 16/9

10:20-16:10

2 stops35h 50m

Chicago O'Hare Intl

Wed 23/9

19:15-20:30

2 stops19h 15m

£623

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Wed 25/11

10:25-16:45

2 stops36h 20m

Chicago O'Hare Intl

Sun 29/11

19:15-18:35

1 stop17h 20m

£638

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Thu 8/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Sun 11/10

19:15-08:55

1 stop31h 40m

£655

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Fri 11/9

09:35-21:37

2 stops18h 02m

Chicago O'Hare Intl

Thu 17/9

07:35-08:55

2 stops19h 20m

£694

ManchesterChicago

MAN Manchester - MDW Chicago Midway

MANMDW

Manchester

Tue 8/9

05:55-16:57

2 stops17h 02m

Chicago Midway

Tue 15/9

13:19-10:10

2 stops14h 51m

£739

Flights are sorted by cheapest return flights first.

Deals found on 4/8

Showing 1-10 of 39 resultsSorted by cheapest first
1
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 much does it cost for a return flight from Sheffield to Chicago?

Airfare is below average for this route at the moment.
Sheffield to Chicago flights typically cost between £579 and £839 in September.
The cheapest return price found within the last 5 days was £505 on Aer Lingus (15 Sept–22 Sept).

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 9 August 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
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Entertainment

7.5

Boarding

7.7

Crew

8.1

Food

6.9

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.
Virgin Atlantic
7.5
Good
694 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Entertainment

7.5

Boarding

7.7

Crew

8.1

Food

6.9

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.
Scandinavian Airlines
7.4
Good
1,932 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Entertainment

7.5

Boarding

7.7

Crew

8.1

Food

6.9

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.
Aer Lingus
7.3
Good
1,691 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Entertainment

7.5

Boarding

7.7

Crew

8.1

Food

6.9

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.
Icelandair
6.9
Okay
726 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Entertainment

7.5

Boarding

7.7

Crew

8.1

Food

6.9

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.
British Airways
6.7
Okay
8,153 reviews
Virgin Atlantic
7.5
Good
694 reviews
Check prices

Comfort

7.3

Overall

7.5

Entertainment

7.5

Boarding

7.7

Crew

8.1

Food

6.9

Reviews

1 / 20
10.0
Excellent

Edwin,May 2026

LHR - LAX

First time flying with Virgin. It was everything I hoped it would be.

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, Icelandair, and Virgin Atlantic can get you from Sheffield to Chicago in just under 14h 20m. Your travel time can differ by up to 19h 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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Grimsby to O'Hare Intl flights
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London City to Peoria flights
Newquay to O'Hare Intl flights
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Gatwick to Champaign flights
Leeds to St. Louis flights
Bristol to Midway flights
Darlington to Midway flights
Southampton to Midway flights
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Doncaster to O'Hare Intl flights
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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 9 August 2026.
AirlineCheapestAverageFlexibilityOn-time
RyanairCheapest£36Average£61FlexibilityNo cancel feeOn-timeN/A
Search Ryanair flights
Scandinavian AirlinesCheapest£377Average£472FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£427Average£598FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£453Average£724FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
Virgin AtlanticCheapest£469Average£689FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
British AirwaysCheapest£473Average£665FlexibilityNo cancel feeOn-time70%
Search British Airways flights
United AirlinesCheapest£498Average£782FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
KLMCheapest£504Average£605FlexibilityNo cancel feeOn-time75%
Search KLM flights
LufthansaCheapest£553Average£732FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
American AirlinesCheapest£558Average£754FlexibilityNo cancel feeOn-time71%
Search American Airlines 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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