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$338+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 28, 2026.

This lol.travel deal was found by Cheapflights users on 1/26. 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 1/26$437
This lol.travel deal was found by Cheapflights users on 1/27. 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.
Tue 2/246:30 am
FLR
-
ORD
2 stops17h 09m
Air Canada
Tue 3/311:11 am
ORD
-
FLR
2 stops18h 24m
Air Canada
Deal found 1/27$597
This United Airlines deal was found by Cheapflights users on 1/25. 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 2/236:50 pm
ORD
-
FLR
1 stop11h 55m
United Airlines
Deal found 1/25$621
This United Airlines deal was found by Cheapflights users on 1/27. 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 2/116:00 pm
ORD
-
FLR
1 stop11h 35m
United Airlines
Deal found 1/27$625
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/237:10 am
FLR
-
ORD
2 stops18h 31m
United Airlines
Mon 3/24:10 pm
ORD
-
FLR
2 stops14h 35m
United Airlines
Deal found 1/26$639
This Delta deal was found by Cheapflights users on 1/28. 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 stops18h 56m
Delta
Wed 2/1110:46 am
MDW
-
FLR
2 stops17h 54m
Delta
Deal found 1/28$703
This Delta deal was found by Cheapflights users on 1/26. 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 3/126:40 am
FLR
-
MDW
2 stops17h 14m
Delta
Thu 3/192:05 pm
MDW
-
FLR
2 stops15h 35m
Delta
Deal found 1/26$1,223
This Delta deal was found by Cheapflights users on 1/27. 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.
Sat 5/96:30 am
FLR
-
MDW
2 stops18h 35m
Delta
Sat 6/65:59 pm
MDW
-
FLR
2 stops16h 16m
Delta
Deal found 1/27$1,544
This Delta deal was found by Cheapflights users on 1/26. 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.
Sun 3/156:40 am
FLR
-
MDW
2 stops21h 51m
Delta
Tue 3/311:10 pm
MDW
-
FLR
2 stops15h 50m
Delta
Deal found 1/26$1,963

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 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$597
(lol.travel)

One-way from

$338
(Kiwi.com)

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 28, 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

Tue 2/24

6:30 am-4:39 pm

2 stops17h 09m

Chicago O'Hare Intl

Tue 3/3

11:11 am-12:35 pm

2 stops18h 24m

$597

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 2/24

6:30 am-1:25 pm

1 stop13h 55m

Chicago O'Hare Intl

Tue 3/3

6:50 pm-6:15 pm

1 stop16h 25m

$621

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

$621

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 2/24

6:30 am-3:20 pm

1 stop15h 50m

Chicago O'Hare Intl

Tue 3/3

4:10 pm-2:00 pm

2 stops14h 50m

$622

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 3/15

11:30 am-3:00 pm

1 stop33h 30m

Chicago O'Hare Intl

Tue 3/31

7:05 pm-6:55 pm

1 stop16h 50m

$624

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 2/23

7:00 pm-4:20 pm

1 stop28h 20m

Chicago O'Hare Intl

Mon 3/2

6:50 pm-6:05 pm

1 stop16h 15m

$628

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 3/12

6:40 am-5:54 pm

2 stops17h 14m

Chicago Midway

Thu 3/19

2:05 pm-11:40 am

2 stops15h 35m

$1,223

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Sat 5/9

6:30 am-6:05 pm

2 stops18h 35m

Chicago Midway

Sat 6/6

5:59 pm-5:15 pm

2 stops16h 16m

$1,544

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Sun 3/15

6:40 am-10:31 pm

2 stops21h 51m

Chicago Midway

Tue 3/31

1:10 pm-12:00 pm

2 stops15h 50m

$1,963

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 5/17

7:00 pm-1:00 pm

2 stops49h 00m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 26 results
1
2
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*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub the most. FlightHub 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 28, 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
9,206 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,206 reviews
United Airlines
7.4
Good
9,206 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
ITA Airways
6.7
Okay
1,131 reviews
United Airlines
7.4
Good
9,206 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 $621, Air Canada 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 KLM, 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

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