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$414+ 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Nov 20 — Nov 271
Thu 11/20
Thu 11/27
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 October 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$467
(oojo)

One-way from

$414
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$613
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. 11% potential increase in price ($91 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 October 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 October 21, 2025.

This oojo deal was found by Cheapflights users on 10/19. 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 oojo 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 10/19$467
This lol.travel deal was found by Cheapflights users on 10/21. 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 12/43:30 pmFLR - ORD
2 stops35h 53mITA Airways
Wed 12/109:19 amORD - FLR
2 stops18h 36mITA Airways
Deal found 10/21$578
This lol.travel deal was found by Cheapflights users on 10/20. 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 11/56:30 amFLR - ORD
2 stops20h 53mITA Airways
Sun 11/910:48 amORD - FLR
2 stops17h 07mITA Airways
Deal found 10/20$630
This Mytrip deal was found by Cheapflights users on 10/20. 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 12/49:00 pmFLR - ORD
2 stops24h 20mMultiple Airlines
Wed 12/104:25 pmORD - FLR
3 stops23h 50mMultiple Airlines
Deal found 10/20$632
This Gotogate deal was found by Cheapflights users on 10/20. 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.
Wed 11/57:00 pmFLR - ORD
1 stop28h 20mSWISS
Sun 11/96:50 pmORD - FLR
1 stop12h 20mSWISS
Deal found 10/20$638
This Expedia deal was found by Cheapflights users on 10/21. 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 11/196:30 amFLR - ORD
1 stop13h 40mLufthansa
Mon 12/299:50 pmORD - FLR
1 stop17h 10mLufthansa
Deal found 10/21$639
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Wed 11/196:30 amFLR - ORD
1 stop13h 40mUnited Airlines
Mon 12/298:51 amORD - FLR
2 stops20h 44mUnited Airlines
Deal found 10/21$640
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Wed 11/56:30 amFLR - ORD
2 stops23h 27mUnited Airlines
Sun 11/96:50 pmORD - FLR
1 stop12h 20mUnited Airlines
Deal found 10/20$643
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Tue 11/186:30 amFLR - ORD
2 stops34h 16mUnited Airlines
Mon 12/299:15 pmORD - FLR
2 stops32h 20mUnited Airlines
Deal found 10/21$645
This Delta deal was found by Cheapflights users on 10/20. 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 11/56:40 amFLR - MDW
2 stops18h 03mDelta
Sun 11/910:47 amMDW - FLR
2 stops15h 08mDelta
Deal found 10/20$686
This Delta deal was found by Cheapflights users on 10/21. 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 - MDW
2 stops18h 20mDelta
Wed 12/101:14 pmMDW - FLR
2 stops15h 26mDelta
Deal found 10/21$692
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 12/312:20 pmFLR - MDW
2 stops18h 27mDelta
Wed 12/1012:50 pmMDW - FLR
2 stops15h 30mDelta
Deal found 10/19$799

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 October 21, 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

$487

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

11:40 am-8:23 pm

2 stops39h 43m

Chicago O'Hare Intl

Wed 12/10

9:19 am-10:40 pm

2 stops30h 21m

$601

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 11/5

6:30 am-8:23 pm

2 stops20h 53m

Chicago O'Hare Intl

Sun 11/9

10:48 am-10:55 am

2 stops17h 07m

$630

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

9:00 pm-2:20 pm

2 stops24h 20m

Chicago O'Hare Intl

Wed 12/10

4:25 pm-11:15 pm

3 stops23h 50m

$632

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 11/5

7:00 pm-4:20 pm

1 stop28h 20m

Chicago O'Hare Intl

Sun 11/9

6:50 pm-2:10 pm

1 stop12h 20m

$638

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 11/19

6:30 am-1:10 pm

1 stop13h 40m

Chicago O'Hare Intl

Mon 12/29

8:51 am-12:35 pm

2 stops20h 44m

$640

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 11/5

6:30 am-10:57 pm

2 stops23h 27m

Chicago O'Hare Intl

Sun 11/9

6:50 pm-2:10 pm

1 stop12h 20m

$643

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 11/18

6:55 pm-12:45 pm

1 stop24h 50m

Chicago O'Hare Intl

Mon 12/29

6:50 pm-8:50 am

1 stop31h 00m

$647

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 4/1

7:05 am-1:50 pm

1 stop13h 45m

Chicago O'Hare Intl

Thu 4/16

9:15 pm-10:20 pm

1 stop18h 05m

$661

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 12/3

2:20 pm-8:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Wed 12/10

9:50 pm-4:30 pm

1 stop11h 40m

$674

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 30 results
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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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 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
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 October 21, 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
8,988 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

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
8,988 reviews
United Airlines
7.4
Good
8,988 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

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.
Lufthansa
6.8
Okay
7,509 reviews
United Airlines
7.4
Good
8,988 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

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.
ITA Airways
6.7
Okay
1,074 reviews
United Airlines
7.4
Good
8,988 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

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.
British Airways
6.7
Okay
7,466 reviews
United Airlines
7.4
Good
8,988 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

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 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 $487, TAP AIR PORTUGAL can have you in Chicago from Florence in 27h 10m. 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 13% 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?

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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 October 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$600Average$947FlexibilityNo cancel feeOn-time79%

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