Cheap flights from Sheffield to Chicago from £298

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 18/3. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

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

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 12 December 2025.

Wed 24/1206:55MAN - ORD
2 stops43h 05mMultiple Airlines
Tue 30/1218:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 11/12£603
Thu 25/1210:10MAN - ORD
1 stop12h 35mMultiple Airlines
Tue 30/1218:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 11/12£627
Tue 23/1217:15MAN - ORD
1 stop27h 45mTAP AIR PORTUGAL
Sun 28/1220:25ORD - MAN
1 stop13h 50mTAP AIR PORTUGAL
Deal found 11/12£636
Thu 25/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Sun 28/1219:20ORD - MAN
1 stop32h 10mScandinavian Airlines
Deal found 11/12£640
Tue 23/1207:25MAN - ORD
2 stops37h 35mMultiple Airlines
Mon 29/1218:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 11/12£660
Wed 24/1211:55MAN - ORD
1 stop11h 25mIcelandair
Mon 29/1218:30ORD - MAN
1 stop10h 15mIcelandair
Deal found 11/12£662
Tue 23/1217:15MAN - ORD
1 stop27h 45mMultiple Airlines
Tue 6/118:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 9/12£667
Fri 26/1212:55MAN - ORD
2 stops27h 10mMultiple Airlines
Tue 30/1218:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 11/12£671
Fri 26/1209:20MAN - ORD
2 stops30h 34mMultiple Airlines
Sun 28/1215:50ORD - MAN
1 stop10h 05mMultiple Airlines
Deal found 11/12£677
Wed 24/1213:30MAN - MDW
1 stop14h 52mDelta
Mon 29/1218:08MDW - MAN
2 stops15h 57mDelta
Deal found 11/12£934
Thu 25/1213:30MAN - MDW
1 stop14h 52mDelta
Tue 30/1218:08MDW - MAN
2 stops15h 57mDelta
Deal found 11/12£962
Fri 26/1205:50MAN - MDW
2 stops17h 36mDelta
Tue 30/1218:08MDW - MAN
2 stops15h 57mDelta
Deal found 11/12£963

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 12 December 2025.

Round-trip from

£406

One-way from

£298

Popular in

July

Cheapest in

February

Average price

£652
Scandinavian Airlines
  • Scandinavian Airlines
  • 12/1-16/1
  • 4 total stops
  • 81h 20m total
  • Sheffield to Chicago
18/3
  • 18/3
  • 2 total stops
  • 32h 05m total
  • Sheffield to Chicago
Highest demand for flights based on searches. 15% potential increase in price (£78 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (£11 potential savings vs. average return price).
Average for round-trip flights in December 2025

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 12 December 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

Thu 12/3

10:10-17:45

1 stop12h 35m

Chicago O'Hare Intl

Wed 25/3

20:20-18:35

1 stop17h 15m

£409

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 3/3

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Wed 25/3

20:20-18:35

1 stop17h 15m

£411

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 4/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sun 8/2

19:10-09:30

1 stop32h 20m

£413

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

20:55-16:45

2 stops25h 50m

Chicago O'Hare Intl

Sun 22/2

19:10-12:15

2 stops35h 05m

£415

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 21/1

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Fri 13/2

19:20-18:35

1 stop17h 15m

£426

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 20/1

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Fri 13/2

19:20-18:35

1 stop17h 15m

£426

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 22/1

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 13/2

19:20-18:35

1 stop17h 15m

£426

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 3/3

13:30-22:44

1 stop15h 14m

Chicago Midway

Wed 25/3

17:38-10:30

1 stop11h 52m

£585

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 13/2

13:25-22:42

1 stop15h 17m

Chicago Midway

Wed 18/2

12:46-08:45

1 stop13h 59m

£593

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 17/3

13:30-22:29

1 stop13h 59m

Chicago Midway

Tue 21/4

17:59-14:00

2 stops14h 01m

£610

Flights are sorted by cheapest return flights first.

Deals found on 10/12

Showing 1-10 of 37 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 5 December 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, 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 £599). 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 12 December 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 12 December 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.

Comfort

7.3

Boarding

7.7

Food

6.9

Crew

8.2

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!

Comfort

7.3

Boarding

7.7

Food

6.9

Crew

8.2

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!

Comfort

7.3

Boarding

7.7

Food

6.9

Crew

8.2

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!

Comfort

7.3

Boarding

7.7

Food

6.9

Crew

8.2

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!

Comfort

7.3

Boarding

7.7

Food

6.9

Crew

8.2

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!

Comfort

7.3

Boarding

7.7

Food

6.9

Crew

8.2

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, 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 39m. 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 £319. Icelandair flights start at £344 while deals on Aer Lingus start at £450 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 £599). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest£369Average£458FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£373Average£622FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
IcelandairCheapest£413Average£536FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
British AirwaysCheapest£442Average£616FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Aer LingusCheapest£452Average£661FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
FinnairCheapest£465Average£706FlexibilityNo cancel feeOn-time76%
Search Finnair flights
KLMCheapest£467Average£668FlexibilityNo cancel feeOn-time75%
Search KLM flights
Virgin AtlanticCheapest£471Average£642FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
LufthansaCheapest£473Average£620FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
United AirlinesCheapest£499Average£630FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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