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$353+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$476
(Mytrip)

One-way from

$353
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$666
Provider with most accurate pricing for Florence Peretola-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Florence Peretola-Chicago (CHI) flights.
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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. 13% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 20, 2025.

This Mytrip deal was found by Cheapflights users on 11/19. 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.
Thu 12/47:15 pmFLR - ORD
1 stop27h 10mTAP AIR PORTUGAL
Wed 12/107:10 pmORD - FLR
1 stop16h 20mTAP AIR PORTUGAL
Deal found 11/19$476
This lol.travel deal was found by Cheapflights users on 11/19. 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 12/43:05 pmFLR - ORD
2 stops34h 15mITA Airways
Wed 12/109:19 amORD - FLR
2 stops18h 36mITA Airways
Deal found 11/19$574
This Delta deal was found by Cheapflights users on 11/18. 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 12/46:40 amFLR - ORD
2 stops18h 47mDelta
Wed 12/105:20 pmORD - FLR
1 stop14h 05mDelta
Deal found 11/18$660
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:15 pmFLR - ORD
1 stop12h 50mLufthansa
Wed 12/106:00 pmORD - FLR
1 stop19h 40mLufthansa
Deal found 11/17$670
This Air Canada deal was found by Cheapflights users on 11/19. 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:35 amFLR - ORD
2 stops15h 20mMultiple Airlines
Wed 12/101:06 pmORD - FLR
2 stops16h 29mMultiple Airlines
Deal found 11/19$690
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Sat 12/138:00 amFLR - ORD
1 stop17h 25mUnited Airlines
Thu 12/186:25 pmORD - FLR
2 stops15h 05mUnited Airlines
Deal found 11/19$721
This Delta deal was found by Cheapflights users on 11/19. 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 11/2112:20 pmFLR - MDW
2 stops18h 20mDelta
Tue 11/251:15 pmMDW - FLR
2 stops18h 10mDelta
Deal found 11/19$1,042
This Trip.com deal was found by Cheapflights users on 11/19. 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.
Sat 12/66:40 amFLR - MDW
2 stops18h 26mKLM
Sat 12/2711:48 amMDW - FLR
2 stops16h 32mKLM
Deal found 11/19$1,162
This Delta deal was found by Cheapflights users on 11/19. 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 12/46:50 amFLR - MDW
2 stops18h 10mDelta
Wed 12/101:50 pmMDW - FLR
2 stops14h 30mDelta
Deal found 11/19$1,340
This Delta deal was found by Cheapflights users on 11/19. 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 12/1812:20 pmFLR - MDW
2 stops18h 27mDelta
Mon 12/226:08 pmMDW - FLR
2 stops13h 17mDelta
Deal found 11/19$1,356
This Delta deal was found by Cheapflights users on 11/19. 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 12/126:40 amFLR - MDW
2 stops18h 20mDelta
Thu 12/1812:45 pmMDW - FLR
2 stops15h 35mDelta
Deal found 11/19$1,576
This Delta deal was found by Cheapflights users on 11/19. 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.
Sat 12/1312:20 pmFLR - MDW
2 stops18h 27mDelta
Thu 12/181:14 pmMDW - FLR
2 stops18h 11mDelta
Deal found 11/19$1,716

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 November 20, 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 12/4

7:15 pm-3:25 pm

1 stop27h 10m

Chicago O'Hare Intl

Wed 12/10

7:10 pm-6:30 pm

1 stop16h 20m

$476

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

6:40 am-6:27 pm

2 stops18h 47m

Chicago O'Hare Intl

Wed 12/10

5:20 pm-2:25 pm

1 stop14h 05m

$660

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Tue 3/3

6:40 am-6:37 pm

2 stops18h 57m

Chicago Midway

Mon 3/9

1:00 pm-11:20 am

2 stops16h 20m

$660

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

2:15 pm-8:05 pm

1 stop12h 50m

Chicago O'Hare Intl

Wed 12/10

6:00 pm-8:40 pm

1 stop19h 40m

$670

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Mon 2/9

6:40 am-5:29 pm

2 stops17h 49m

Chicago Midway

Mon 2/16

10:53 am-8:55 am

2 stops15h 02m

$671

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

6:35 am-2:55 pm

2 stops15h 20m

Chicago O'Hare Intl

Wed 12/10

1:06 pm-12:35 pm

2 stops16h 29m

$690

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

2:15 pm-11:32 pm

2 stops16h 17m

Chicago O'Hare Intl

Wed 12/10

9:50 pm-4:30 pm

1 stop11h 40m

$730

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 5/7

6:30 am-8:42 am

2 stops33h 12m

Chicago Midway

Mon 5/11

1:00 pm-2:25 pm

2 stops18h 25m

$751

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 5/7

7:00 am-6:31 pm

2 stops18h 31m

Chicago Midway

Mon 5/11

5:59 pm-10:45 pm

2 stops21h 46m

$814

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Sat 12/6

6:40 am-6:06 pm

2 stops18h 26m

Chicago Midway

Sat 12/27

11:48 am-11:20 am

2 stops16h 32m

$1,162

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 22 results
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2
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Compare providers for flights from Florence to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Florence to Chicago in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Florence-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Florence-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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 November 20, 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
9,029 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,029 reviews
United Airlines
7.4
Good
9,029 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Lufthansa
6.8
Okay
7,579 reviews
United Airlines
7.4
Good
9,029 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
ITA Airways
6.7
Okay
1,086 reviews
United Airlines
7.4
Good
9,029 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
British Airways
6.7
Okay
7,534 reviews
United Airlines
7.4
Good
9,029 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 1 airline. 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 $670, TAP AIR PORTUGAL can have you in Chicago from Florence in 12h 50m. There are 4680 mi between Florence and Chicago. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Florence to Chicago round-trip?

    Currently priced at $600, SWISS will fly you from Florence to Chicago and back. In addition to SWISS, many other airlines offer competitively priced options for your trip. SWISS is priced at 19% lower than the current average price of a flight leaving 3 months from now.

  • 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top airline flying from Florence to Chicago

Discover the top airline that operate flights from Florence to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$600Average$942FlexibilityNo cancel feeOn-time79%

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