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Cheap flights from Sheffield to Chicago from £224

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 22/11. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
16 Nov — 23 Nov1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Sheffield to Chicago are usually found in February or January, booked 59 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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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 17 October 2025.

Sat 22/1108:45MAN - ORD
1 stop15h 10mMultiple Airlines
Sat 29/1115:50ORD - MAN
1 stop10h 10mMultiple Airlines
Deal found 16/10£416
Sat 1/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sat 15/1119:20ORD - MAN
2 stops18h 25mScandinavian Airlines
Deal found 16/10£417
Sat 22/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Sat 29/1119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 16/10£418
Sun 23/1109:20MAN - ORD
2 stops37h 25mScandinavian Airlines
Sun 30/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 16/10£425
Tue 16/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Mon 12/119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 15/10£430
Wed 12/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Wed 19/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 15/10£433
Tue 4/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Sun 9/1119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 15/10£434
Mon 15/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Thu 15/119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 15/10£466
Mon 15/1205:50MAN - MDW
2 stops18h 28mDelta
Thu 15/113:00MDW - MAN
2 stops15h 10mDelta
Deal found 15/10£652
Tue 4/1113:30MAN - MDW
1 stop14h 44mVirgin Atlantic
Tue 16/1210:49MDW - MAN
2 stops15h 06mVirgin Atlantic
Deal found 16/10£656
Fri 21/1113:25MAN - MDW
1 stop16h 15mDelta
Fri 28/1109:41MDW - MAN
2 stops16h 39mDelta
Deal found 15/10£666
Sat 22/1113:30MAN - MDW
1 stop16h 10mDelta
Sat 29/1113:15MDW - MAN
2 stops17h 30mDelta
Deal found 16/10£669

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 17 October 2025.

Round-trip from

£416

One-way from

£224

Popular in

July

Cheapest in

February

Average price

£575
22/11-29/11
  • 22/11-29/11
  • 2 total stops
  • 25h 20m total
  • Sheffield to Chicago
Search Deals
22/11
  • 22/11
  • 2 total stops
  • 28h 15m total
  • Sheffield to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£77 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 October 2025
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 17 October 2025.
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

Sat 22/11

08:45-17:55

1 stop15h 10m

Chicago O'Hare Intl

Sat 29/11

15:50-08:00

1 stop10h 10m

£416

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/3

19:15-16:55

1 stop27h 40m

Chicago O'Hare Intl

Mon 9/3

20:20-17:55

2 stops16h 35m

£416

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 1/11

10:10-17:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 15/11

19:20-19:45

2 stops18h 25m

£417

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 22/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 29/11

19:20-12:15

2 stops34h 55m

£420

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 16/12

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 12/1

19:20-18:35

1 stop17h 15m

£430

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 7/1

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Wed 4/3

19:20-18:35

1 stop17h 15m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 12/11

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Wed 19/11

19:20-18:35

1 stop17h 15m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 13/2

19:20-08:40

2 stops31h 20m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 17/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 21/11

19:20-08:40

2 stops31h 20m

£469

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

20:55-16:45

2 stops25h 50m

Chicago O'Hare Intl

Fri 13/2

19:20-18:35

1 stop17h 15m

£478

Flights are sorted by cheapest return flights first.

Deals found on 16/10

Showing 1-10 of 34 results
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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 10 October 2025.

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, May is the cheapest month in which you can book a flight from Sheffield to Chicago (average of £142). Flying from Sheffield to Chicago in July is currently the most expensive (average of £598). 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.

What is the cheapest time of day to fly from SH9 to CHI?

Find hourly flight availability from Sheffield to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 17 October 2025.

A simple way to save on the total cost of your ticket is to fly from Sheffield to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight at midday.

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 17 October 2025.
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
670 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

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
670 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

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
7.4
Good
1,533 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

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
1,341 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

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
556 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

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
7,457 reviews
Virgin Atlantic
7.5
Good
670 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.5

Food

6.9

Overall

7.5

Boarding

7.7

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 14h 16m. Your travel time can differ by up to 13h 24m. There are 3816 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.

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

    Currently, May is the cheapest month in which you can book a flight from Sheffield to Chicago (average of £142). Flying from Sheffield to Chicago in July is currently the most expensive (average of £598). 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 17 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest£365Average£459FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£372Average£620FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
IcelandairCheapest£416Average£531FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
British AirwaysCheapest£441Average£611FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Aer LingusCheapest£447Average£647FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
FinnairCheapest£464Average£704FlexibilityNo cancel feeOn-time76%
Search Finnair flights
KLMCheapest£464Average£611FlexibilityNo cancel feeOn-time75%
Search KLM flights
LufthansaCheapest£471Average£618FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Virgin AtlanticCheapest£481Average£613FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£497Average£628FlexibilityNo cancel feeOn-time69%
Search United 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.

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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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