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$359+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This Mytrip deal was found by Cheapflights users on 3/14. 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.
Fri 4/176:50 pm
FLR
-
ORD
1 stop28h 15m
TAP AIR PORTUGAL
Wed 4/226:00 pm
ORD
-
FLR
1 stop17h 05m
TAP AIR PORTUGAL
Deal found 3/14$521
This Trip.com deal was found by Cheapflights users on 3/15. 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 4/166:50 pm
FLR
-
ORD
1 stop28h 10m
TAP AIR PORTUGAL
Wed 4/226:00 pm
ORD
-
FLR
1 stop33h 50m
TAP AIR PORTUGAL
Deal found 3/15$523
This oojo deal was found by Cheapflights users on 3/13. 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.
Mon 4/2711:25 am
FLR
-
ORD
2 stops38h 19m
ITA Airways
Mon 5/43:00 pm
ORD
-
FLR
1 stop24h 40m
ITA Airways
Deal found 3/13$587
This lol.travel deal was found by Cheapflights users on 3/16. 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.
Wed 4/87:05 am
FLR
-
ORD
1 stop18h 10m
British Airways
Tue 4/217:05 pm
ORD
-
FLR
1 stop20h 15m
British Airways
Deal found 3/16$638
This lol.travel deal was found by Cheapflights users on 3/16. 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 11/2311:40 am
FLR
-
ORD
1 stop14h 05m
British Airways
Mon 11/309:45 pm
ORD
-
FLR
1 stop30h 35m
British Airways
Deal found 3/16$640
This lol.travel deal was found by Cheapflights users on 3/17. 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.
Sat 4/186:55 pm
FLR
-
ORD
1 stop28h 05m
TAP AIR PORTUGAL
Sat 4/256:05 pm
ORD
-
FLR
1 stop16h 45m
TAP AIR PORTUGAL
Deal found 3/17$646
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/198:15 pm
FLR
-
ORD
1 stop25h 15m
Air Serbia
Sat 7/2511:20 pm
ORD
-
FLR
1 stop13h 20m
Air Serbia
Deal found 3/15$650
This Iberia deal was found by Cheapflights users on 3/13. 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.
Mon 4/276:45 am
FLR
-
ORD
1 stop14h 40m
Multiple Airlines
Mon 5/47:05 pm
ORD
-
FLR
1 stop20h 15m
Multiple Airlines
Deal found 3/13$659
This British Airways deal was found by Cheapflights users on 3/13. 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.
Thu 4/167:05 am
FLR
-
ORD
1 stop15h 50m
British Airways
Wed 4/227:05 pm
ORD
-
FLR
1 stop33h 55m
British Airways
Deal found 3/13$661
This Delta deal was found by Cheapflights users on 3/16. 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.
Wed 4/86:30 am
FLR
-
MDW
2 stops17h 52m
Delta
Tue 4/211:24 pm
MDW
-
FLR
2 stops15h 46m
Delta
Deal found 3/16$677
This Delta deal was found by Cheapflights users on 3/15. 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 4/166:30 am
FLR
-
MDW
2 stops18h 28m
Delta
Wed 4/226:38 pm
MDW
-
FLR
2 stops17h 22m
Delta
Deal found 3/15$682
This Delta deal was found by Cheapflights users on 3/16. 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.
Mon 11/236:40 am
FLR
-
MDW
2 stops18h 30m
Delta
Mon 11/301:00 pm
MDW
-
FLR
2 stops15h 20m
Delta
Deal found 3/16$688

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$511
(Mytrip)

One-way from

$359
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$901
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. 3% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 17, 2026.
Use the filters below to find and compare flights from Florence to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Wed 4/8

6:30 am-6:40 pm

2 stops19h 10m

Chicago Midway

Tue 4/21

1:24 pm-11:30 am

2 stops15h 06m

$680

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 4/16

6:30 am-5:58 pm

2 stops18h 28m

Chicago Midway

Wed 4/22

6:38 pm-7:00 pm

2 stops17h 22m

$682

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 4/27

7:40 pm-2:15 pm

1 stop25h 35m

Chicago O'Hare Intl

Mon 5/4

5:10 pm-5:15 pm

1 stop17h 05m

$684

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/30

6:30 am-2:15 pm

1 stop14h 45m

Chicago O'Hare Intl

Thu 5/7

4:20 pm-7:00 pm

1 stop19h 40m

$695

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 4/27

12:40 pm-11:59 pm

2 stops18h 19m

Chicago O'Hare Intl

Mon 5/4

1:36 pm-12:10 pm

2 stops15h 34m

$695

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Mon 4/27

6:30 am-5:58 pm

2 stops18h 28m

Chicago Midway

Mon 5/4

1:24 pm-11:30 am

2 stops15h 06m

$695

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/23

11:20 am-11:59 pm

2 stops19h 39m

Chicago O'Hare Intl

Thu 4/30

4:20 pm-4:50 pm

1 stop17h 30m

$698

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/23

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Mon 4/27

7:15 pm-7:05 pm

1 stop16h 50m

$723

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 4/17

6:40 am-6:52 pm

2 stops19h 12m

Chicago O'Hare Intl

Wed 4/22

4:50 pm-4:50 pm

1 stop17h 00m

$748

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Fri 4/17

6:40 am-5:58 pm

2 stops18h 18m

Chicago Midway

Wed 4/22

6:38 pm-7:00 pm

2 stops17h 22m

$748

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/15

Showing 1-10 of 38 resultsSorted by cheapest first
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2
3
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  • 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 $396). Flying from Florence to Chicago in June is currently the most expensive (average of $896). 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 March 17, 2026.
Get a feel of what it's like to fly with United Airlines 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
9,431 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

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
9,431 reviews
United Airlines
7.4
Good
9,431 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

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 $677, Delta can have you in Chicago from Florence in 17h 52m. 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 American Airlines, with whom users have recently found tickets for as low as $445. However, be on the lookout for offers from British Airways and Lufthansa, 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 $396). Flying from Florence to Chicago in June is currently the most expensive (average of $896). 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
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Hammond
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