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$405+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Jan 10 — Jan 171
Sat 1/10
Sat 1/17
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 December 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:15 pmFLR - ORD
1 stop12h 10mMultiple Airlines
Mon 12/153:20 pmORD - FLR
1 stop11h 20mMultiple Airlines
Deal found 12/9$1,315
This Iberia deal was found by Cheapflights users on 12/11. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:55 amFLR - ORD
1 stop15h 00mMultiple Airlines
Thu 12/185:10 pmORD - FLR
1 stop11h 35mMultiple Airlines
Deal found 12/11$1,334
This Iberia deal was found by Cheapflights users on 12/11. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:30 pmFLR - ORD
2 stops27h 30mMultiple Airlines
Thu 12/185:10 pmORD - FLR
1 stop11h 35mMultiple Airlines
Deal found 12/11$1,469
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/139:35 amFLR - ORD
1 stop34h 10mUnited Airlines
Thu 12/181:24 pmORD - FLR
2 stops16h 11mUnited Airlines
Deal found 12/10$1,668
This United Airlines deal was found by Cheapflights users on 12/9. 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.
Fri 12/126:30 amFLR - ORD
1 stop15h 50mUnited Airlines
Thu 12/185:50 pmORD - FLR
2 stops15h 40mUnited Airlines
Deal found 12/9$1,680
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 12/1311:05 amFLR - ORD
2 stops16h 30mDelta
Thu 12/1811:15 amORD - FLR
2 stops17h 25mDelta
Deal found 12/10$1,752
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 12/1311:05 amFLR - MDW
2 stops19h 42mDelta
Thu 12/1812:45 pmMDW - FLR
2 stops15h 55mDelta
Deal found 12/10$1,752
This Delta deal was found by Cheapflights users on 12/10. 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.
Fri 12/126:40 amFLR - MDW
2 stops18h 20mDelta
Thu 12/1812:45 pmMDW - FLR
2 stops15h 55mDelta
Deal found 12/10$1,809

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 December 11, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$477
(Mytrip)

One-way from

$405
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$1,040
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. 1% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 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

Thu 1/15

7:15 pm-3:25 pm

1 stop27h 10m

Chicago O'Hare Intl

Wed 1/21

7:10 pm-6:30 pm

1 stop16h 20m

$477

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/8

11:25 am-6:12 pm

2 stops37h 47m

Chicago O'Hare Intl

Thu 6/4

11:15 am-10:40 am

2 stops16h 25m

$618

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 5/6

6:25 am-1:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Thu 6/4

11:15 am-6:15 pm

2 stops24h 00m

$639

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 5/5

7:00 pm-1:10 pm

1 stop25h 10m

Chicago O'Hare Intl

Thu 6/4

11:15 am-2:45 pm

2 stops20h 30m

$639

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 5/10

6:25 am-1:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Thu 6/4

11:15 am-6:15 pm

2 stops24h 00m

$639

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/8

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Thu 6/4

7:15 pm-7:05 pm

1 stop16h 50m

$658

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 5/7

7:00 pm-1:10 pm

1 stop25h 10m

Chicago O'Hare Intl

Thu 6/4

11:15 am-10:40 am

2 stops16h 25m

$668

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 5/11

6:25 am-1:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Thu 6/4

11:15 am-6:15 pm

2 stops24h 00m

$668

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 1/15

6:35 am-7:45 pm

2 stops20h 10m

Chicago O'Hare Intl

Wed 1/21

4:50 pm-6:30 pm

2 stops18h 40m

$694

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 1/15

6:40 am-6:32 pm

2 stops18h 52m

Chicago Midway

Wed 1/21

10:46 am-8:55 am

2 stops15h 09m

$709

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 33 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 December.
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

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 $409). Flying from Florence to Chicago in June is currently the most expensive (average of $819). 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 December 11, 2025.
Get a feel of what it's like to fly with United Airlines 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
9,094 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

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
9,094 reviews
United Airlines
7.4
Good
9,094 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

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
1,100 reviews
United Airlines
7.4
Good
9,094 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

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 $709, TAP AIR PORTUGAL can have you in Chicago from Florence in 18h 52m. There are 4682 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 20% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Florence to Chicago one-way?

    The cheapest airline one-way is British Airways, with whom users have recently found tickets for as low as $490. However, be on the lookout for offers from SWISS 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 $409). Flying from Florence to Chicago in June is currently the most expensive (average of $819). 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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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 December 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$600Average$942FlexibilityNo cancel feeOn-time79%

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