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Cheap flights from Sheffield to Chicago from £289

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 26/8. Fares are subject to change and may not be available on all flights or dates of travel.
MAN — CHI
18 Jun — 25 Jun1
1 adult

Cheapflights Tip: The best prices from Sheffield to Chicago are usually found in February or January, booked 77 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 13 June 2025.

Round-trip from

£491

One-way from

£289

Popular in

July

Cheapest in

February

Average price

£601
Virgin Atlantic
  • Virgin Atlantic
  • 22/9-29/9
  • 4 total stops
  • 40h 36m total
  • Sheffield to Chicago
Search Deals
26/8
  • 26/8
  • 2 total stops
  • 43h 55m total
  • Sheffield to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£70 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 June 2025
Search Deals

Find flight deals from Sheffield to Chicago

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 13 June 2025.

Mon 22/905:55MAN - MDW
2 stops18h 41mVirgin Atlantic
Mon 29/909:30MDW - MAN
2 stops21h 55mVirgin Atlantic
Deal found 11/6£491
Mon 1/905:55MAN - ORD
1 stop14h 45mVirgin Atlantic
Wed 24/910:35ORD - MAN
2 stops15h 45mVirgin Atlantic
Deal found 11/6£491
Thu 7/808:50MAN - ORD
1 stop11h 10mMultiple Airlines
Sun 17/815:45ORD - MAN
1 stop10h 25mMultiple Airlines
Deal found 12/6£494
Thu 11/911:50MAN - ORD
1 stop11h 43mAir Canada
Thu 18/920:25ORD - MAN
1 stop31h 55mAir Canada
Deal found 11/6£497
Fri 3/1020:25MAN - ORD
2 stops25h 45mScandinavian Airlines
Sun 5/1019:15ORD - MAN
2 stops18h 30mScandinavian Airlines
Deal found 10/6£497
Mon 1/907:00MAN - ORD
1 stop12h 50mBritish Airways
Fri 12/922:35ORD - MAN
1 stop12h 45mBritish Airways
Deal found 10/6£501
Mon 3/1105:55MAN - MDW
2 stops18h 41mDelta
Mon 1/1217:59MDW - MAN
2 stops15h 56mDelta
Deal found 11/6£502
Sun 2/1113:40MAN - ORD
1 stop30h 50mDelta
Tue 2/1209:35ORD - MAN
2 stops16h 45mDelta
Deal found 11/6£502
Thu 4/911:50MAN - ORD
1 stop11h 43mUnited Airlines
Thu 11/912:00ORD - MAN
2 stops15h 55mUnited Airlines
Deal found 11/6£523
Wed 18/605:55MAN - ORD
1 stop14h 15mKLM
Wed 25/616:20ORD - MAN
1 stop11h 25mKLM
Deal found 10/6£538
Sun 2/1117:45MAN - ORD
2 stops26h 15mAustrian Airlines
Fri 28/1116:20ORD - MAN
2 stops16h 30mAustrian Airlines
Deal found 11/6£561
Fri 17/1012:40MAN - ORD
1 stop14h 35mIcelandair
Tue 28/1019:30ORD - MAN
1 stop10h 15mIcelandair
Deal found 11/6£575

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 13 June 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 - MDW

MANMDW

Manchester

Mon 22/9

05:55-18:36

2 stops18h 41m

Chicago Midway

Mon 29/9

09:30-13:25

2 stops21h 55m

£491

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 1/9

05:55-14:40

1 stop14h 45m

Chicago O'Hare Intl

Wed 24/9

10:35-08:20

2 stops15h 45m

£491

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 7/8

08:50-14:00

1 stop11h 10m

Chicago O'Hare Intl

Sun 17/8

15:45-08:10

1 stop10h 25m

£494

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 11/9

11:50-17:33

1 stop11h 43m

Chicago O'Hare Intl

Thu 18/9

20:25-10:20

1 stop31h 55m

£497

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 3/10

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Sun 5/10

19:15-19:45

2 stops18h 30m

£497

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 1/9

07:00-13:50

1 stop12h 50m

Chicago O'Hare Intl

Fri 12/9

22:35-17:20

1 stop12h 45m

£501

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 3/11

05:55-18:36

2 stops18h 41m

Chicago Midway

Mon 1/12

17:59-15:55

2 stops15h 56m

£502

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 2/11

13:40-14:30

1 stop30h 50m

Chicago O'Hare Intl

Tue 2/12

09:35-08:20

2 stops16h 45m

£502

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 4/9

11:50-17:33

1 stop11h 43m

Chicago O'Hare Intl

Thu 11/9

12:00-09:55

2 stops15h 55m

£523

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 2/11

17:45-14:00

2 stops26h 15m

Chicago O'Hare Intl

Fri 28/11

16:20-14:50

2 stops16h 30m

£561

Flights are sorted by cheapest return flights first.

Deals found on 12/6

Showing 1-10 of 32 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 9 June 2025.

To ensure you get the cheapest price possible for a flight from Sheffield to Chicago, you should look to book at least 77 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 £595). Flying from Sheffield to Chicago in July is currently the most expensive (average of £843). 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 13 June 2025.

When flying from Sheffield to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Sheffield to Chicago?

Use this chart to determine the cheapest time to fly return from Sheffield to Chicago. Price data was last updated on 3 November 2024.

Travellers seeking maximum savings on their Sheffield to Chicago flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 13 June 2025.
Read reviews from past customers who have flown Delta, KLM and Austrian Airlines from Sheffield to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very Good
7,950 reviews
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,358 reviews
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Austrian Airlines
7.6
Good
802 reviews
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Finnair
7.6
Good
1,290 reviews
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,463 reviews
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Sheffield to Chicago one-way?

    To fly one-way, consider booking your trip with Icelandair, which is currently one of the cheapest options available, starting at £444. British Airways flights start at £486 while deals on Aer Lingus start at £523 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 £595). Flying from Sheffield to Chicago in July is currently the most expensive (average of £843). 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.
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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 13 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest£354Average£465FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
IcelandairCheapest£363Average£524FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£413Average£611FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
British AirwaysCheapest£430Average£602FlexibilityNo cancel feeOn-time70%
Search British Airways flights
FinnairCheapest£458Average£606FlexibilityNo cancel feeOn-time76%
Search Finnair flights
KLMCheapest£459Average£593FlexibilityNo cancel feeOn-time75%
Search KLM flights
LufthansaCheapest£466Average£617FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Virgin AtlanticCheapest£480Average£596FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
United AirlinesCheapest£489Average£621FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air FranceCheapest£494Average£830FlexibilityNo cancel feeOn-time77%
Search Air France 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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