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$364+ 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
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
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 12, 2026.

This lol.travel deal was found by Cheapflights users on 3/8. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:50 pm
FLR
-
ORD
1 stop28h 15m
TAP AIR PORTUGAL
Fri 5/16:00 pm
ORD
-
FLR
1 stop17h 00m
TAP AIR PORTUGAL
Deal found 3/8$512
This lol.travel deal was found by Cheapflights users on 3/11. 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.
Fri 4/176:50 pm
FLR
-
ORD
1 stop28h 15m
TAP AIR PORTUGAL
Fri 4/246:00 pm
ORD
-
FLR
1 stop34h 00m
TAP AIR PORTUGAL
Deal found 3/11$515
This lol.travel deal was found by Cheapflights users on 3/10. 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.
Fri 5/17:00 pm
FLR
-
ORD
1 stop25h 10m
ITA Airways
Thu 5/73:00 pm
ORD
-
FLR
1 stop16h 45m
ITA Airways
Deal found 3/10$539
This lol.travel deal was found by Cheapflights users on 3/9. 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 4/27:05 am
FLR
-
ORD
1 stop18h 10m
British Airways
Mon 4/67:05 pm
ORD
-
FLR
1 stop20h 15m
British Airways
Deal found 3/9$597
This Air Serbia deal was found by Cheapflights users on 3/10. 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 Serbia 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 3/10$608
This Expedia deal was found by Cheapflights users on 3/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:05 am
FLR
-
ORD
1 stop13h 45m
British Airways
Wed 4/299:15 pm
ORD
-
FLR
1 stop18h 05m
British Airways
Deal found 3/8$609
This Iberia deal was found by Cheapflights users on 3/7. 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.
Fri 4/246:45 am
FLR
-
ORD
1 stop14h 40m
Multiple Airlines
Fri 5/17:05 pm
ORD
-
FLR
1 stop20h 15m
Multiple Airlines
Deal found 3/7$612
This Scandinavian Airlines deal was found by Cheapflights users on 3/8. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Mon 4/277:15 pm
ORD
-
FLR
1 stop16h 50m
Scandinavian Airlines
Deal found 3/8$622
This Delta deal was found by Cheapflights users on 3/9. 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 4/26:30 am
FLR
-
MDW
2 stops17h 52m
Delta
Mon 4/66:34 pm
MDW
-
FLR
2 stops15h 41m
Delta
Deal found 3/9$688
This Delta deal was found by Cheapflights users on 3/10. 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 11/136:40 am
FLR
-
MDW
2 stops18h 30m
Delta
Sun 11/221:00 pm
MDW
-
FLR
2 stops15h 40m
Delta
Deal found 3/10$724
This Delta deal was found by Cheapflights users on 3/9. 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 12/226:40 am
FLR
-
MDW
2 stops18h 30m
Delta
Sat 1/91:00 pm
MDW
-
FLR
2 stops15h 20m
Delta
Deal found 3/9$896
This Delta deal was found by Cheapflights users on 3/10. 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 4/246:40 am
FLR
-
MDW
2 stops18h 18m
Delta
Fri 5/11:24 pm
MDW
-
FLR
2 stops15h 46m
Delta
Deal found 3/10$931

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 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$512
(lol.travel)

One-way from

$364
(Air Serbia)

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 ($28 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 12, 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 - ORD

FLRORD

Florence Peretola

Wed 4/22

7:05 am-5:04 pm

2 stops16h 59m

Chicago O'Hare Intl

Wed 4/29

5:00 pm-10:20 pm

1 stop22h 20m

$615

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/23

12:40 pm-2:15 pm

1 stop32h 35m

Chicago O'Hare Intl

Thu 4/30

5:10 pm-7:40 pm

1 stop19h 30m

$671

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/2

6:30 am-4:43 pm

2 stops17h 13m

Chicago O'Hare Intl

Mon 4/6

5:40 pm-2:25 pm

2 stops13h 45m

$688

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 4/2

6:30 am-5:22 pm

2 stops17h 52m

Chicago Midway

Mon 4/6

6:34 pm-5:15 pm

2 stops15h 41m

$688

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sat 6/6

5:20 pm-4:10 pm

2 stops29h 50m

Chicago O'Hare Intl

Tue 6/9

7:00 am-7:05 pm

2 stops29h 05m

$726

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/23

6:30 am-7:55 pm

1 stop20h 25m

Chicago O'Hare Intl

Mon 4/27

7:05 pm-2:10 pm

1 stop12h 05m

$743

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sat 4/25

6:30 am-2:50 pm

1 stop15h 20m

Chicago O'Hare Intl

Sat 5/2

11:00 am-12:40 pm

2 stops18h 40m

$748
Quickest round-trip

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/8

8:15 am-2:00 pm

1 stop12h 45m

Chicago O'Hare Intl

Thu 6/4

6:30 pm-12:50 pm

1 stop11h 20m

$758

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Fri 4/24

6:40 am-5:58 pm

2 stops18h 18m

Chicago Midway

Fri 5/1

1:24 pm-12:10 pm

2 stops15h 46m

$931

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Wed 6/24

6:30 am-6:05 pm

2 stops18h 35m

Chicago Midway

Tue 7/21

10:35 am-8:55 am

2 stops15h 20m

$977

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 31 resultsSorted by cheapest first
1
2
3
4
  • 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 12, 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
9,418 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Boarding

7.7

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
9,418 reviews
United Airlines
7.4
Good
9,418 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Boarding

7.7

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 $596, 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 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 Delta, 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
Porter
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Alternative routes for Florence to Chicago

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