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$366+ 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 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 21, 2026.

This lol.travel deal was found by Cheapflights users on 1/20. 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.
Thu 2/57:15 pm
FLR
-
ORD
1 stop27h 10m
TAP AIR PORTUGAL
Wed 2/117:10 pm
ORD
-
FLR
1 stop16h 20m
TAP AIR PORTUGAL
Deal found 1/20$455
This Gotogate deal was found by Cheapflights users on 1/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:15 pm
FLR
-
ORD
2 stops25h 45m
Air Canada
Sat 11/1412:00 pm
ORD
-
FLR
2 stops14h 40m
Air Canada
Deal found 1/20$595
This lol.travel deal was found by Cheapflights users on 1/21. 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 3/211:40 am
FLR
-
ORD
1 stop14h 05m
British Airways
Mon 3/910:45 pm
ORD
-
FLR
1 stop30h 35m
British Airways
Deal found 1/21$597
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:30 am
FLR
-
ORD
2 stops18h 18m
Multiple Airlines
Tue 2/242:00 pm
ORD
-
FLR
2 stops16h 40m
Multiple Airlines
Deal found 1/20$610
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:30 am
FLR
-
ORD
1 stop15h 50m
United Airlines
Tue 2/244:10 pm
ORD
-
FLR
1 stop14h 50m
United Airlines
Deal found 1/20$611
This United Airlines deal was found by Cheapflights users on 1/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:30 am
FLR
-
ORD
1 stop15h 50m
United Airlines
Mon 2/238:50 am
ORD
-
FLR
2 stops24h 40m
United Airlines
Deal found 1/19$614
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/56:30 am
FLR
-
ORD
1 stop15h 50m
United Airlines
Wed 2/111:00 pm
ORD
-
FLR
2 stops17h 35m
United Airlines
Deal found 1/20$616
This Delta deal was found by Cheapflights users on 1/20. 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.
Tue 2/176:40 am
FLR
-
MDW
2 stops18h 05m
Delta
Tue 2/241:49 pm
MDW
-
FLR
2 stops14h 36m
Delta
Deal found 1/20$682
This Delta deal was found by Cheapflights users on 1/19. 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 2/56:40 am
FLR
-
MDW
2 stops17h 49m
Delta
Wed 2/1110:46 am
MDW
-
FLR
2 stops17h 54m
Delta
Deal found 1/19$685
This Delta deal was found by Cheapflights users on 1/20. 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.
Fri 11/66:50 am
FLR
-
MDW
2 stops18h 47m
Delta
Sat 11/141:00 pm
MDW
-
FLR
2 stops18h 25m
Delta
Deal found 1/20$807
This Expedia deal was found by Cheapflights users on 1/21. 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 2/56:50 am
FLR
-
MDW
2 stops17h 39m
KLM
Wed 2/116:14 pm
MDW
-
FLR
2 stops15h 06m
KLM
Deal found 1/21$825
This Delta deal was found by Cheapflights users on 1/19. 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 1/296:40 am
FLR
-
MDW
2 stops18h 56m
Delta
Tue 2/310:48 am
MDW
-
FLR
2 stops15h 07m
Delta
Deal found 1/19$831

Find 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 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$453
(lol.travel)

One-way from

$366
(Air Serbia)

Popular in

December

Cheapest in

February

Average price

$648
Provider with most accurate pricing for Florence Peretola-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Florence Peretola-Chicago (CHI) flights.
Search Deals
From Florence Peretola to Chicago (CHI)
Search Deals
One-way flight from Florence Peretola to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 21, 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 2/5

7:15 pm-3:25 pm

1 stop27h 10m

Chicago O'Hare Intl

Wed 2/11

7:10 pm-6:30 pm

1 stop16h 20m

$453

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 2/19

6:30 am-3:20 pm

1 stop15h 50m

Chicago O'Hare Intl

Mon 2/23

6:50 pm-1:45 pm

1 stop11h 55m

$609

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 2/17

6:30 am-5:48 pm

2 stops18h 18m

Chicago O'Hare Intl

Tue 2/24

2:00 pm-1:40 pm

2 stops16h 40m

$610

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 2/17

6:30 am-3:20 pm

1 stop15h 50m

Chicago O'Hare Intl

Tue 2/24

1:02 pm-2:00 pm

2 stops17h 58m

$611

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 3/5

6:30 am-3:20 pm

1 stop15h 50m

Chicago O'Hare Intl

Thu 4/2

9:40 pm-8:15 pm

1 stop15h 35m

$612

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 2/5

6:30 am-1:25 pm

1 stop13h 55m

Chicago O'Hare Intl

Wed 2/11

1:00 pm-1:35 pm

2 stops17h 35m

$614

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Tue 2/17

6:40 am-5:45 pm

2 stops18h 05m

Chicago Midway

Tue 2/24

1:49 pm-11:25 am

2 stops14h 36m

$682

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 2/5

6:40 am-5:29 pm

2 stops17h 49m

Chicago Midway

Wed 2/11

10:46 am-11:40 am

2 stops17h 54m

$685

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 2/5

6:50 am-5:29 pm

2 stops17h 39m

Chicago Midway

Wed 2/11

6:14 pm-4:20 pm

2 stops15h 06m

$825

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Fri 5/8

6:30 am-6:05 pm

2 stops18h 35m

Chicago Midway

Sat 6/6

5:59 pm-5:15 pm

2 stops16h 16m

$898

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 29 results
1
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3

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*
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Florence-Chicago flight deals on Cheapflights vs. FlightHub >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 AranGrant the most. AranGrant 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 21, 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
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,191 reviews
United Airlines
7.4
Good
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
ITA Airways
6.7
Okay
1,130 reviews
United Airlines
7.4
Good
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 $609, TAP AIR PORTUGAL can have you in Chicago from Florence in 15h 50m. 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 American Airlines and ITA Airways, 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
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