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$348+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Cheap flight deals from Florence to Chicago

Best flights from Florence to Chicago
Discover carefully curated flight deals from Florence to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This American Airlines deal was found by Cheapflights users on 1/1. 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.
Tue 4/1412:20 pmFLR - ORD
1 stop31h 00mAmerican Airlines
Thu 4/2310:35 pmORD - FLR
1 stop29h 55mAmerican Airlines
Deal found 1/1$618
This British Airways deal was found by Cheapflights users on 1/1. 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.
Tue 4/1412:20 pmFLR - ORD
2 stops30h 57mBritish Airways
Thu 4/231:44 pmORD - FLR
2 stops25h 36mBritish Airways
Deal found 1/1$627
This Scandinavian Airlines deal was found by Cheapflights users on 1/1. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:55 pmFLR - ORD
1 stop27h 15mScandinavian Airlines
Mon 4/207:15 pmORD - FLR
1 stop16h 50mScandinavian Airlines
Deal found 1/1$635
This Delta deal was found by Cheapflights users on 12/31. 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 1/166:40 amFLR - ORD
1 stop14h 40mDelta
Tue 1/202:25 pmORD - FLR
2 stops17h 00mDelta
Deal found 12/31$649
This KLM deal was found by Cheapflights users on 12/31. 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.
Thu 1/225:00 pmFLR - ORD
1 stop28h 20mMultiple Airlines
Wed 1/2811:16 amORD - FLR
2 stops14h 39mMultiple Airlines
Deal found 12/31$649
This American Airlines deal was found by Cheapflights users on 1/1. 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.
Tue 4/147:05 amFLR - ORD
1 stop14h 55mAmerican Airlines
Tue 4/216:00 pmORD - FLR
1 stop21h 20mAmerican Airlines
Deal found 1/1$618
This British Airways deal was found by Cheapflights users on 1/1. 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.
Mon 4/137:05 amFLR - ORD
2 stops22h 29mBritish Airways
Tue 4/215:00 pmORD - FLR
1 stop11h 35mBritish Airways
Deal found 1/1$631
This Scandinavian Airlines deal was found by Cheapflights users on 1/1. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:55 pmFLR - ORD
1 stop27h 15mScandinavian Airlines
Wed 4/227:15 pmORD - FLR
1 stop16h 50mScandinavian Airlines
Deal found 1/1$635
This Delta deal was found by Cheapflights users on 1/1. 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 2/136:40 amFLR - MDW
2 stops19h 00mDelta
Tue 2/171:28 pmMDW - FLR
2 stops17h 57mDelta
Deal found 1/1$654
This Trip.com deal was found by Cheapflights users on 1/1. 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.
Thu 1/226:40 amFLR - MDW
2 stops18h 15mMultiple Airlines
Wed 1/2810:46 amMDW - FLR
2 stops15h 09mMultiple Airlines
Deal found 1/1$684
This British Airways deal was found by Cheapflights users on 1/1. 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.
Mon 4/137:05 amFLR - ORD
2 stops22h 29mBritish Airways
Sun 4/195:00 pmORD - FLR
1 stop11h 50mBritish Airways
Deal found 1/1$631
This Scandinavian Airlines deal was found by Cheapflights users on 1/1. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:55 pmFLR - ORD
1 stop27h 15mScandinavian Airlines
Sat 4/187:15 pmORD - FLR
1 stop16h 50mScandinavian Airlines
Deal found 1/1$635
This Delta deal was found by Cheapflights users on 1/1. 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 1/226:40 amFLR - MDW
2 stops18h 15mDelta
Wed 1/281:49 pmMDW - FLR
2 stops14h 36mDelta
Deal found 1/1$654
This British Airways deal was found by Cheapflights users on 1/1. 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.
Mon 4/137:05 amFLR - ORD
2 stops21h 51mBritish Airways
Mon 4/205:00 pmORD - FLR
1 stop11h 30mBritish Airways
Deal found 1/1$631
This Delta deal was found by Cheapflights users on 12/31. 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 1/166:50 amFLR - MDW
2 stops17h 47mDelta
Tue 1/209:32 amMDW - FLR
2 stops18h 53mDelta
Deal found 12/31$660
This Delta deal was found by Cheapflights users on 1/1. 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 2/156:40 amFLR - MDW
2 stops16h 34mDelta
Sun 2/226:17 pmMDW - FLR
2 stops18h 33mDelta
Deal found 1/1$666
This Delta deal was found by Cheapflights users on 1/1. 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 2/146:40 amFLR - MDW
2 stops16h 34mDelta
Wed 2/1810:49 amMDW - FLR
2 stops17h 36mDelta
Deal found 1/1$666
This Delta deal was found by Cheapflights users on 1/1. 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 7/16:30 amFLR - MDW
2 stops18h 35mDelta
Wed 8/125:59 pmMDW - FLR
2 stops13h 26mDelta
Deal found 1/1$1,144
This Delta deal was found by Cheapflights users on 1/1. 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 6/16:30 amFLR - MDW
2 stops18h 35mDelta
Mon 6/1510:35 amMDW - FLR
2 stops15h 25mDelta
Deal found 1/1$1,170

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 January 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$454
(Trip.com)

One-way from

$348
(Kiwi.com)

Popular in

December

Cheapest in

February
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. 15% potential increase in price ($127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
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 January 2, 2026.
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

Tue 4/14

12:20 pm-12:20 pm

1 stop31h 00m

Chicago O'Hare Intl

Thu 4/23

10:35 pm-11:30 am

1 stop29h 55m

$618

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 4/14

7:05 am-3:00 pm

1 stop14h 55m

Chicago O'Hare Intl

Tue 4/21

6:00 pm-10:20 pm

1 stop21h 20m

$618

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 4/14

12:20 pm-12:17 pm

2 stops30h 57m

Chicago O'Hare Intl

Thu 4/23

1:44 pm-10:20 pm

2 stops25h 36m

$627

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 4/13

7:05 am-10:34 pm

2 stops22h 29m

Chicago O'Hare Intl

Tue 4/21

5:00 pm-11:35 am

1 stop11h 35m

$631

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 4/13

7:05 am-10:34 pm

2 stops22h 29m

Chicago O'Hare Intl

Sun 4/19

5:00 pm-11:50 am

1 stop11h 50m

$631

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 4/13

7:05 am-9:56 pm

2 stops21h 51m

Chicago O'Hare Intl

Mon 4/20

5:00 pm-11:30 am

1 stop11h 30m

$631

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 4/12

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Mon 4/20

7:15 pm-7:05 pm

1 stop16h 50m

$635

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 4/12

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Wed 4/22

7:15 pm-7:05 pm

1 stop16h 50m

$635

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 4/14

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Sat 4/18

7:15 pm-7:05 pm

1 stop16h 50m

$635

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 1/16

6:40 am-2:20 pm

1 stop14h 40m

Chicago O'Hare Intl

Tue 1/20

2:25 pm-2:25 pm

2 stops17h 00m

$649

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 35 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 January.
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 January 2, 2026.
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
9,133 reviews

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,133 reviews
United Airlines
7.4
Good
9,133 reviews

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
ITA Airways
6.7
Okay
1,117 reviews
United Airlines
7.4
Good
9,133 reviews

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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 $654, American Airlines can have you in Chicago from Florence in 19h. There are 4682 mi between Florence and Chicago. This flight may include one or multiple stops.

  • 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 ITA Airways and SWISS, 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
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