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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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$587
(British Airways)

One-way from

$366
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$692
From Florence Peretola to Chicago (CHI)
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One-way flight from Florence Peretola to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($93 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This British Airways deal was found by Cheapflights users on 9/11. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:05 amFLR - ORD
1 stop18h 10mBritish Airways
Mon 10/279:45 pmORD - FLR
1 stop31h 35mBritish Airways
Deal found 9/11$587
This Iberia deal was found by Cheapflights users on 9/10. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:05 amFLR - ORD
1 stop13h 50mMultiple Airlines
Sat 11/15:45 pmORD - FLR
1 stop12h 25mMultiple Airlines
Deal found 9/10$608
This KLM deal was found by Cheapflights users on 9/10. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:40 pmFLR - ORD
1 stop25h 30mKLM
Sun 10/55:10 pmORD - FLR
1 stop17h 10mKLM
Deal found 9/10$614
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:30 amFLR - MDW
2 stops18h 55mDelta
Mon 10/2710:35 amMDW - FLR
2 stops16h 20mDelta
Deal found 9/11$618
This British Airways deal was found by Cheapflights users on 9/10. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:05 amFLR - ORD
1 stop13h 45mBritish Airways
Fri 10/316:36 pmORD - FLR
2 stops17h 19mBritish Airways
Deal found 9/10$630
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:05 amFLR - ORD
2 stops21h 18mAmerican Airlines
Mon 10/277:25 pmORD - FLR
1 stop13h 10mAmerican Airlines
Deal found 9/11$631
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/2311:20 amFLR - ORD
2 stops19h 30mDelta
Mon 10/276:59 pmORD - FLR
2 stops13h 26mDelta
Deal found 9/10$638
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 10/16:30 amFLR - ORD
2 stops18h 29mDelta
Sun 10/55:10 pmORD - FLR
1 stop17h 10mDelta
Deal found 9/10$667
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/2311:20 amFLR - ORD
2 stops19h 30mDelta
Sat 11/16:20 pmORD - FLR
1 stop11h 00mDelta
Deal found 9/10$690
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1512:20 pmFLR - MDW
2 stops18h 12mDelta
Wed 12/316:00 pmMDW - FLR
2 stops13h 25mDelta
Deal found 9/11$758
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:40 amFLR - MDW
2 stops16h 56mDelta
Fri 1/29:29 amMDW - FLR
2 stops17h 56mDelta
Deal found 9/11$764
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:40 amFLR - MDW
2 stops18h 20mDelta
Thu 1/111:48 amMDW - FLR
2 stops16h 32mDelta
Deal found 9/11$829

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 September 11, 2025.
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

Fri 10/24

7:05 am-3:55 pm

1 stop15h 50m

Chicago O'Hare Intl

Fri 10/31

6:10 pm-5:55 pm

1 stop17h 45m

$589

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 10/23

7:05 am-1:55 pm

1 stop13h 50m

Chicago O'Hare Intl

Sat 11/1

5:45 pm-12:10 pm

1 stop12h 25m

$608

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 10/1

7:40 pm-2:10 pm

1 stop25h 30m

Chicago O'Hare Intl

Sun 10/5

5:10 pm-5:20 pm

1 stop17h 10m

$614

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 10/23

6:30 am-6:25 pm

2 stops18h 55m

Chicago Midway

Mon 10/27

10:35 am-8:55 am

2 stops16h 20m

$618

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 10/23

11:20 am-11:50 pm

2 stops19h 30m

Chicago O'Hare Intl

Mon 10/27

6:59 pm-2:25 pm

2 stops13h 26m

$638

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 10/1

6:30 am-5:59 pm

2 stops18h 29m

Chicago O'Hare Intl

Sun 10/5

5:10 pm-5:20 pm

1 stop17h 10m

$667

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

$668

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Mon 12/15

12:20 pm-11:32 pm

2 stops18h 12m

Chicago Midway

Wed 12/31

6:00 pm-2:25 pm

2 stops13h 25m

$758

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Wed 12/17

6:40 am-4:36 pm

2 stops16h 56m

Chicago Midway

Thu 1/1

11:48 am-11:20 am

2 stops16h 32m

$758

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Wed 12/17

6:40 am-4:36 pm

2 stops16h 56m

Chicago Midway

Fri 1/2

9:29 am-10:25 am

2 stops17h 56m

$764

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 31 results
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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
No data available for this route at this time. Please check back soon.

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 September 11, 2025.
Get a feel of what it's like to fly with United Airlines, Lufthansa, 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
8,937 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
Lufthansa
6.8
Okay
7,409 reviews
United Airlines
7.4
Good
8,937 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
ITA Airways
6.7
Okay
1,036 reviews
United Airlines
7.4
Good
8,937 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
British Airways
6.7
Okay
7,361 reviews
United Airlines
7.4
Good
8,937 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

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 $589, British Airways 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.

  • 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, August is the cheapest month in which you can book a flight from Florence to Chicago (average of $245). Flying from Florence to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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