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$330+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 16, 2025.

Round-trip from

$437
(lol.travel)

One-way from

$330
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$693
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. 12% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 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 16, 2025.

This lol.travel deal was found by Cheapflights users on 9/16. 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.
Thu 11/67:15 pmFLR - ORD
1 stop27h 00mTAP AIR PORTUGAL
Wed 11/127:10 pmORD - FLR
1 stop16h 20mTAP AIR PORTUGAL
Deal found 9/16$437
This lol.travel deal was found by Cheapflights users on 9/15. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:30 amFLR - ORD
2 stops15h 25mAir Canada
Sun 11/3010:00 amORD - FLR
2 stops16h 40mAir Canada
Deal found 9/15$552
This Gotogate deal was found by Cheapflights users on 9/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:30 amFLR - ORD
1 stop13h 40mLufthansa
Sun 11/309:50 pmORD - FLR
1 stop11h 40mLufthansa
Deal found 9/15$572
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:20 pmFLR - ORD
1 stop31h 05mAmerican Airlines
Wed 11/126:30 pmORD - FLR
1 stop12h 35mAmerican Airlines
Deal found 9/15$575
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:30 amFLR - ORD
2 stops20h 30mUnited Airlines
Sun 11/306:50 pmORD - FLR
1 stop12h 20mUnited Airlines
Deal found 9/15$576
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:15 pmFLR - ORD
1 stop27h 40mSWISS
Mon 10/207:05 pmORD - FLR
1 stop12h 00mSWISS
Deal found 9/14$577
This lol.travel deal was found by Cheapflights users on 9/15. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:25 amFLR - ORD
1 stop13h 45mITA Airways
Sun 9/283:00 pmORD - FLR
1 stop16h 45mITA Airways
Deal found 9/15$579
This Iberia deal was found by Cheapflights users on 9/16. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:55 amFLR - ORD
1 stop14h 35mMultiple Airlines
Wed 11/123:08 pmORD - FLR
2 stops15h 57mMultiple Airlines
Deal found 9/16$581
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:40 amFLR - ORD
2 stops23h 35mUnited Airlines
Mon 10/207:05 pmORD - FLR
1 stop12h 00mUnited Airlines
Deal found 9/14$582
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:15 pmFLR - ORD
2 stops25h 58mUnited Airlines
Wed 11/126:50 pmORD - FLR
1 stop12h 00mUnited Airlines
Deal found 9/15$583
This Delta deal was found by Cheapflights users on 9/15. 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 11/66:40 amFLR - MDW
2 stops16h 34mDelta
Wed 11/121:14 pmMDW - FLR
2 stops15h 06mDelta
Deal found 9/15$608
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 11/236:40 amFLR - MDW
2 stops18h 28mDelta
Sun 11/301:14 pmMDW - FLR
2 stops15h 06mDelta
Deal found 9/15$620

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 16, 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

Thu 11/6

7:15 pm-3:15 pm

1 stop27h 00m

Chicago O'Hare Intl

Wed 11/12

7:10 pm-6:30 pm

1 stop16h 20m

$437

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 11/23

6:30 am-2:55 pm

2 stops15h 25m

Chicago O'Hare Intl

Sun 11/30

10:00 am-9:40 am

2 stops16h 40m

$564

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 11/23

6:30 am-1:10 pm

1 stop13h 40m

Chicago O'Hare Intl

Sun 11/30

9:50 pm-4:30 pm

1 stop11h 40m

$572

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 11/6

3:20 pm-3:25 pm

1 stop31h 05m

Chicago O'Hare Intl

Wed 11/12

3:08 pm-2:05 pm

2 stops15h 57m

$575

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

9:17 am-1:45 pm

2 stops21h 28m

$576

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 11/23

6:30 am-8:00 pm

2 stops20h 30m

Chicago O'Hare Intl

Sun 11/30

6:50 pm-2:10 pm

1 stop12h 20m

$576

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 11/6

6:40 am-4:14 pm

2 stops16h 34m

Chicago Midway

Wed 11/12

1:14 pm-11:20 am

2 stops15h 06m

$608

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Sun 11/23

12:20 pm-11:32 pm

2 stops18h 12m

Chicago Midway

Sun 11/30

1:14 pm-11:20 am

2 stops15h 06m

$620

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 10/2

6:30 am-5:35 pm

2 stops18h 05m

Chicago Midway

Mon 10/6

6:23 pm-2:25 pm

2 stops13h 02m

$620

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 10/30

6:40 am-6:25 pm

2 stops17h 45m

Chicago Midway

Thu 11/6

5:09 pm-4:20 pm

2 stops16h 11m

$724

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 26 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

How much does it cost to fly round-trip from Florence to Chicago?

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 16, 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
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
7,407 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
7,363 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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 $572, TAP AIR PORTUGAL can have you in Chicago from Florence in 13h 40m. 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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