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$367+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
feb. 7 — feb. 141
sáb. 2/7
sáb. 2/14
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 enero 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$556
(oojo)

One-way from

$367
(Kiwi.com)

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 enero 8, 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.
jue. 2/197:15 pmFLR - ORD
1 stop27h 10mTAP AIR PORTUGAL
vie. 2/278:15 pmORD - FLR
1 stop32h 20mTAP AIR PORTUGAL
Deal found 1/6$556
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/57:05 amFLR - ORD
1 stop15h 50mBritish Airways
sáb. 6/64:53 pmORD - FLR
2 stops22h 27mBritish Airways
Deal found 1/6$620
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.
jue. 2/196:00 pmFLR - ORD
2 stops30h 20mMultiple Airlines
vie. 2/276:30 pmORD - FLR
2 stops21h 35mMultiple Airlines
Deal found 1/6$622
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/67:05 amFLR - ORD
2 stops19h 15mBritish Airways
vie. 6/54:53 pmORD - FLR
2 stops22h 27mBritish Airways
Deal found 1/6$626
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/117:05 amFLR - ORD
2 stops22h 29mBritish Airways
sáb. 6/65:34 pmORD - FLR
2 stops21h 46mBritish Airways
Deal found 1/6$630
This Iberia deal was found by Cheapflights users on 1/7. 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.
jue. 1/226:55 amFLR - ORD
1 stop15h 00mMultiple Airlines
mié. 1/282:50 pmORD - FLR
2 stops16h 50mMultiple Airlines
Deal found 1/7$645
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/87:05 amFLR - ORD
1 stop18h 10mBritish Airways
vie. 6/55:34 pmORD - FLR
2 stops21h 46mBritish Airways
Deal found 1/6$661
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/196:55 amFLR - ORD
1 stop15h 00mIberia
vie. 2/276:30 pmORD - FLR
2 stops18h 15mIberia
Deal found 1/6$678
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/57:05 amFLR - ORD
1 stop13h 45mBritish Airways
jue. 6/49:40 pmORD - FLR
2 stops17h 40mBritish Airways
Deal found 1/6$682
This Iberia deal was found by Cheapflights users on 1/7. 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.
jue. 2/196:55 amFLR - ORD
1 stop15h 00mIberia
lun. 2/235:40 pmORD - FLR
1 stop16h 10mIberia
Deal found 1/7$683
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.
jue. 5/710:05 pmFLR - ORD
2 stops22h 45mIberia
vie. 6/510:35 pmORD - FLR
2 stops38h 00mIberia
Deal found 1/6$684
This Delta deal was found by Cheapflights users on 1/8. 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.
jue. 1/226:40 amFLR - MDW
2 stops17h 49mDelta
mié. 1/281:49 pmMDW - FLR
2 stops14h 36mDelta
Deal found 1/8$747

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 enero 8, 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

jue. 5/7

7:05 am-6:15 pm

1 stop18h 10m

Chicago O'Hare Intl

sáb. 6/6

10:35 pm-10:20 pm

1 stop16h 45m

$620

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

mié. 5/6

12:35 pm-3:55 pm

1 stop34h 20m

Chicago O'Hare Intl

sáb. 6/6

10:35 pm-10:20 pm

1 stop16h 45m

$620

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

mié. 5/6

12:35 pm-12:30 pm

1 stop30h 55m

Chicago O'Hare Intl

mar. 6/9

3:54 pm-10:20 pm

2 stops23h 26m

$620

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

mié. 5/6

12:35 pm-1:50 pm

1 stop32h 15m

Chicago O'Hare Intl

vie. 6/5

4:53 pm-10:20 pm

2 stops22h 27m

$620

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

mar. 5/5

7:05 am-3:55 pm

1 stop15h 50m

Chicago O'Hare Intl

mar. 6/9

6:30 pm-10:20 pm

2 stops20h 50m

$620

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

mar. 5/5

7:05 am-1:50 pm

1 stop13h 45m

Chicago O'Hare Intl

lun. 6/8

5:34 pm-10:20 pm

2 stops21h 46m

$620

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

mar. 5/5

7:05 am-3:55 pm

1 stop15h 50m

Chicago O'Hare Intl

sáb. 6/6

4:53 pm-10:20 pm

2 stops22h 27m

$620

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

jue. 5/7

12:20 pm-6:15 pm

1 stop12h 55m

Chicago O'Hare Intl

mar. 6/9

6:30 pm-10:20 pm

2 stops20h 50m

$620

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

jue. 1/22

6:40 am-5:29 pm

2 stops17h 49m

Chicago Midway

mié. 1/28

1:49 pm-11:25 am

2 stops14h 36m

$747

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

jue. 2/19

6:50 am-6:40 pm

2 stops18h 50m

Chicago Midway

vie. 2/27

9:50 am-10:25 am

2 stops17h 35m

$817

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 34 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 enero 8, 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
9,143 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

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
9,143 reviews
United Airlines
7.4
Good
9,143 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

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
9,143 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

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 $747, British Airways can have you in Chicago from Florence in 17h 49m. There are 4682 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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