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$363+ 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
Απρ 14 — Απρ 211
Τρι 4/14
Τρι 4/21
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 Μάρτιος 15, 2026.

This Mytrip deal was found by Cheapflights users on 3/12. 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.
Παρ 5/111:25 am
FLR
-
ORD
1 stop32h 45m
ITA Airways
Πεμ 5/73:00 pm
ORD
-
FLR
1 stop16h 45m
ITA Airways
Deal found 3/12$511
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.
Παρ 4/176:50 pm
FLR
-
ORD
1 stop28h 15m
TAP AIR PORTUGAL
Παρ 4/246:00 pm
ORD
-
FLR
1 stop34h 00m
TAP AIR PORTUGAL
Deal found 3/11$515
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.
Παρ 4/176:50 pm
FLR
-
ORD
1 stop28h 15m
TAP AIR PORTUGAL
Τετ 4/226:00 pm
ORD
-
FLR
1 stop17h 05m
TAP AIR PORTUGAL
Deal found 3/14$521
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.
Δευ 4/2711:25 am
FLR
-
ORD
2 stops38h 19m
ITA Airways
Δευ 5/43:00 pm
ORD
-
FLR
1 stop24h 40m
ITA Airways
Deal found 3/13$587
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Παρ 5/87:00 pm
FLR
-
ORD
1 stop25h 10m
ITA Airways
Πεμ 6/47:33 am
ORD
-
FLR
2 stops27h 42m
ITA Airways
Deal found 3/12$606
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.
Παρ 11/1312:50 pm
FLR
-
ORD
1 stop32h 00m
British Airways
Κυρ 11/229:45 pm
ORD
-
FLR
1 stop33h 50m
British Airways
Deal found 3/10$627
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Τετ 4/86:30 am
FLR
-
MDW
2 stops19h 10m
Delta
Τρι 4/211:24 pm
MDW
-
FLR
2 stops15h 06m
Delta
Deal found 3/14$680
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Δευ 4/276:30 am
FLR
-
MDW
2 stops18h 28m
Delta
Δευ 5/41:24 pm
MDW
-
FLR
2 stops15h 06m
Delta
Deal found 3/13$695
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.
Παρ 11/136:40 am
FLR
-
MDW
2 stops18h 30m
Delta
Κυρ 11/221:00 pm
MDW
-
FLR
2 stops15h 40m
Delta
Deal found 3/10$724
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Πεμ 4/166:30 am
FLR
-
MDW
2 stops19h 06m
Delta
Τετ 4/226:38 pm
MDW
-
FLR
2 stops17h 22m
Delta
Deal found 3/13$745
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Παρ 4/176:40 am
FLR
-
MDW
2 stops18h 18m
Delta
Τετ 4/226:38 pm
MDW
-
FLR
2 stops17h 22m
Delta
Deal found 3/14$748
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Τετ 12/236:40 am
FLR
-
MDW
2 stops22h 05m
Delta
Κυρ 1/105:59 pm
MDW
-
FLR
2 stops18h 51m
Delta
Deal found 3/13$905

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 Μάρτιος 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$511
(Mytrip)

One-way from

$363
(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 ($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 Μάρτιος 15, 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

Παρ 4/24

6:45 am-2:25 pm

1 stop14h 40m

Chicago O'Hare Intl

Παρ 5/1

7:05 pm-10:20 pm

1 stop20h 15m

$645

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Τετ 4/8

6:30 am-6:40 pm

2 stops19h 10m

Chicago Midway

Τρι 4/21

1:24 pm-11:30 am

2 stops15h 06m

$680

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Δευ 4/27

7:40 pm-2:15 pm

1 stop25h 35m

Chicago O'Hare Intl

Δευ 5/4

5:10 pm-5:15 pm

1 stop17h 05m

$684

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Δευ 4/27

12:40 pm-11:59 pm

2 stops18h 19m

Chicago O'Hare Intl

Δευ 5/4

1:36 pm-12:10 pm

2 stops15h 34m

$695

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Δευ 4/27

6:30 am-5:58 pm

2 stops18h 28m

Chicago Midway

Δευ 5/4

1:24 pm-11:30 am

2 stops15h 06m

$695

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Παρ 4/24

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Παρ 5/1

7:15 pm-9:50 am

2 stops31h 35m

$712

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Πεμ 4/23

6:30 am-7:55 pm

1 stop20h 25m

Chicago O'Hare Intl

Δευ 4/27

7:05 pm-2:10 pm

1 stop12h 05m

$743

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Πεμ 4/16

6:30 am-6:36 pm

2 stops19h 06m

Chicago Midway

Τετ 4/22

6:38 pm-7:00 pm

2 stops17h 22m

$745

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Σαβ 4/25

6:30 am-2:50 pm

1 stop15h 20m

Chicago O'Hare Intl

Σαβ 5/2

11:00 am-12:40 pm

2 stops18h 40m

$748

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Παρ 4/17

6:40 am-6:52 pm

2 stops19h 12m

Chicago O'Hare Intl

Τετ 4/22

4:50 pm-4:50 pm

1 stop17h 00m

$748

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 37 resultsSorted by cheapest first
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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 Μάρτιος 15, 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
9,427 reviews

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

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
9,427 reviews
United Airlines
7.4
Good
9,427 reviews

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

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 $680, Delta can have you in Chicago from Florence in 19h 10m. 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
Merrillville
Hammond
Porter
Benton Harbor

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