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$369+ Cheap flights from Florence (FLR) to Chicago (CHI)

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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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Cheap flight deals from Florence to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Florence (FLR) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$556
(oojo)

One-way from

$369
(Air Serbia)

Popular in

December

Cheapest in

February
Provider with most accurate pricing for Florence Peretola-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Florence Peretola-Chicago (CHI) flights.
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From Florence Peretola to Chicago (CHI)
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One-way flight from Florence Peretola to Chicago (CHI)
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Highest demand for flights based on searches. 15% potential increase in price ($129 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
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Find flight deals from Florence to Chicago

Cheapest flights from Florence to Chicago
Explore the most affordable flight options available from Florence to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

This oojo deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:15 pmFLR - ORD
1 stop27h 10mTAP AIR PORTUGAL
Fri 2/278:15 pmORD - FLR
1 stop32h 20mTAP AIR PORTUGAL
Deal found 1/6$556
This Trip.com deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 pmFLR - ORD
2 stops30h 20mMultiple Airlines
Fri 2/276:30 pmORD - FLR
2 stops21h 35mMultiple Airlines
Deal found 1/6$622
This Vueling Global deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vueling Global is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/226:55 amFLR - ORD
1 stop15h 00mMultiple Airlines
Mon 1/265:40 pmORD - FLR
1 stop16h 10mMultiple Airlines
Deal found 1/5$631
This lol.travel deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1211:40 amFLR - ORD
1 stop34h 45mBritish Airways
Thu 2/55:10 pmORD - FLR
1 stop11h 35mBritish Airways
Deal found 1/5$643
This Iberia deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/226:55 amFLR - ORD
1 stop15h 00mMultiple Airlines
Wed 1/282:50 pmORD - FLR
2 stops16h 50mMultiple Airlines
Deal found 1/6$644
This Expedia deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/156:55 amFLR - ORD
1 stop15h 00mIberia
Sun 3/15:40 pmORD - FLR
1 stop16h 10mIberia
Deal found 1/6$649
This Iberia deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:55 amFLR - ORD
1 stop15h 00mIberia
Thu 2/265:40 pmORD - FLR
1 stop22h 20mIberia
Deal found 1/5$651
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2212:20 pmFLR - ORD
2 stops18h 36mDelta
Wed 1/281:58 pmORD - FLR
2 stops14h 27mDelta
Deal found 1/5$653
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/226:40 amFLR - MDW
2 stops17h 49mDelta
Mon 1/2610:46 amMDW - FLR
2 stops15h 09mDelta
Deal found 1/5$653
This Expedia deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/138:30 pmFLR - ORD
1 stop25h 25mIberia
Sun 3/15:40 pmORD - FLR
1 stop16h 10mIberia
Deal found 1/6$659
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:20 pmFLR - ORD
2 stops18h 36mDelta
Thu 2/2610:36 amORD - FLR
2 stops15h 19mDelta
Deal found 1/5$665
This Air France deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:15 pmFLR - MDW
2 stops17h 16mMultiple Airlines
Thu 2/261:28 pmMDW - FLR
2 stops15h 12mMultiple Airlines
Deal found 1/5$735

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florence 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 2,558,603 searches. Data last updated January 6, 2026.
Use the filters below to find and compare flights from Florence to Chicago that are best for you.

Fly from

Florence

Fly to

Chicago

Route

Depart

Return

Price

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 2/19

7:15 pm-3:25 pm

1 stop27h 10m

Chicago O'Hare Intl

Fri 2/27

8:15 pm-11:35 am

1 stop32h 20m

$556

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 2/19

6:00 pm-5:20 pm

2 stops30h 20m

Chicago O'Hare Intl

Fri 2/27

6:30 pm-11:05 pm

2 stops21h 35m

$622

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 1/22

6:55 am-2:55 pm

1 stop15h 00m

Chicago O'Hare Intl

Mon 1/26

5:40 pm-4:50 pm

1 stop16h 10m

$631

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 1/16

6:55 am-2:55 pm

1 stop15h 00m

Chicago O'Hare Intl

Thu 1/22

5:40 pm-11:00 pm

1 stop22h 20m

$649

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 1/22

12:20 pm-11:56 pm

2 stops18h 36m

Chicago O'Hare Intl

Mon 1/26

10:29 am-8:55 am

2 stops15h 26m

$653

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 1/22

6:40 am-5:29 pm

2 stops17h 49m

Chicago Midway

Mon 1/26

10:46 am-8:55 am

2 stops15h 09m

$653

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 2/19

6:55 am-2:55 pm

1 stop15h 00m

Chicago O'Hare Intl

Fri 2/27

6:30 pm-7:45 pm

2 stops18h 15m

$678

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 2/19

6:55 am-2:55 pm

1 stop15h 00m

Chicago O'Hare Intl

Mon 2/23

5:40 pm-4:50 pm

1 stop16h 10m

$684

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 1/22

6:35 am-3:20 pm

1 stop15h 45m

Chicago O'Hare Intl

Wed 1/28

9:50 pm-4:30 pm

1 stop11h 40m

$700

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 6/28

8:15 pm-2:30 pm

1 stop25h 15m

Chicago O'Hare Intl

Wed 8/12

4:40 pm-8:40 am

1 stop33h 00m

$706

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 32 results
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Compare providers for flights from Florence to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Florence to Chicago in January.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Florence-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Florence-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Florence-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Florence-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Florence-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Florence to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Florence with our price prediction graph.
Estimated round-trip 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 Florence to Chicago

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

Currently, September is the cheapest month in which you can book a flight from Florence to Chicago (average of $409). Flying from Florence to Chicago in June is currently the most expensive (average of $819). 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.

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 January 6, 2026.
Get a feel of what it's like to fly with United Airlines and ITA Airways from Florence 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.
United Airlines
7.4
Good
9,138 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,138 reviews
United Airlines
7.4
Good
9,138 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
ITA Airways
6.7
Okay
1,126 reviews
United Airlines
7.4
Good
9,138 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

Related info for your journey

Find useful and relevant information for your journey from Florence to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Florence to Chicago?

    Most people fly from Florence Peretola (FLR) if they book a flight from Florence to Chicago. On average, Peretola has 0 outbound flights to Chicago per day from 0 airlines. Florence Peretola is conveniently located just 3.7 mi from Florence’s city center.

  • How long is the flight from Florence to Chicago?

    For as low as $649, TAP AIR PORTUGAL can have you in Chicago from Florence in 15h. There are 4680 mi between Florence and Chicago. This flight may include one or multiple stops.

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

    The cheapest airline one-way is British Airways, with whom users have recently found tickets for as low as $490. However, be on the lookout for offers from ITA Airways and SWISS, as they are both options that can get you from Florence to Chicago for a low price.

  • Can I find deals for flights from Florence to Chicago that include hotel bookings?

    Yes. In addition to deals on Florence to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florence to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florence to Chicago.

  • Can I find deals for business class flights from Florence to Chicago?

    Yes. Cheapflights offers flight deals from Florence 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 Florence to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Florence to Chicago (average of $409). Flying from Florence to Chicago in June is currently the most expensive (average of $819). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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