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$395+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
May 3 — May 101
Sun 5/3
Sun 5/10
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 April 3, 2026.

This lol.travel deal was found by Cheapflights users on 3/31. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:00 pm
FLR
-
ORD
1 stop25h 10m
ITA Airways
Thu 5/73:00 pm
ORD
-
FLR
1 stop12h 40m
ITA Airways
Deal found 3/31$514
This ITA Airways deal was found by Cheapflights users on 4/1. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:00 pm
FLR
-
ORD
1 stop25h 10m
ITA Airways
Sun 6/283:00 pm
ORD
-
FLR
1 stop20h 15m
ITA Airways
Deal found 4/1$588
This lol.travel deal was found by Cheapflights users on 4/2. 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.
Fri 4/107:05 am
FLR
-
ORD
1 stop15h 50m
British Airways
Tue 4/219:15 pm
ORD
-
FLR
1 stop18h 05m
British Airways
Deal found 4/2$632
This British Airways deal was found by Cheapflights users on 3/30. 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.
Thu 11/123:20 pm
FLR
-
ORD
1 stop34h 25m
British Airways
Mon 11/166:50 pm
ORD
-
FLR
1 stop12h 45m
British Airways
Deal found 3/30$661
This Mytrip deal was found by Cheapflights users on 4/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:50 pm
FLR
-
ORD
2 stops29h 20m
Multiple Airlines
Thu 5/73:00 pm
ORD
-
FLR
2 stops20h 10m
Multiple Airlines
Deal found 4/1$664
This Priceline deal was found by Cheapflights users on 3/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:05 am
FLR
-
ORD
1 stop14h 50m
Multiple Airlines
Mon 5/410:30 pm
ORD
-
FLR
1 stop16h 50m
Multiple Airlines
Deal found 3/30$665
This British Airways deal was found by Cheapflights users on 4/2. 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.
Thu 4/97:05 am
FLR
-
ORD
1 stop15h 50m
British Airways
Tue 4/219:15 pm
ORD
-
FLR
1 stop18h 05m
British Airways
Deal found 4/2$667
This Delta deal was found by Cheapflights users on 3/30. 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 4/226:30 am
FLR
-
MDW
2 stops19h 06m
Delta
Mon 5/41:24 pm
MDW
-
FLR
2 stops15h 06m
Delta
Deal found 3/30$682
This Delta deal was found by Cheapflights users on 3/30. 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 4/276:30 am
FLR
-
MDW
2 stops19h 06m
Delta
Mon 5/41:24 pm
MDW
-
FLR
2 stops15h 06m
Delta
Deal found 3/30$694
This Delta deal was found by Cheapflights users on 4/2. 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 4/96:30 am
FLR
-
MDW
2 stops18h 24m
Delta
Mon 4/2010:41 am
MDW
-
FLR
2 stops15h 14m
Delta
Deal found 4/2$745
This Delta deal was found by Cheapflights users on 4/2. 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 4/116:30 am
FLR
-
MDW
2 stops18h 24m
Delta
Wed 4/221:24 pm
MDW
-
FLR
2 stops15h 46m
Delta
Deal found 4/2$757
This Delta deal was found by Cheapflights users on 3/30. 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 4/226:30 am
FLR
-
MDW
2 stops19h 06m
Delta
Wed 5/271:22 pm
MDW
-
FLR
2 stops15h 48m
Delta
Deal found 3/30$806

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 April 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$514
(lol.travel)

One-way from

$395
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$638
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. 3% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 3, 2026.
Use the filters below to find and compare flights from Florence to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 4/22

6:30 am-2:30 pm

1 stop15h 00m

Chicago O'Hare Intl

Mon 5/4

5:04 pm-2:25 pm

2 stops14h 21m

$677

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Wed 4/22

6:30 am-6:36 pm

2 stops19h 06m

Chicago Midway

Mon 5/4

1:24 pm-11:30 am

2 stops15h 06m

$682

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 4/27

6:30 am-2:30 pm

1 stop15h 00m

Chicago O'Hare Intl

Mon 5/4

1:36 pm-12:10 pm

2 stops15h 34m

$689

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/1

2:50 pm-1:10 pm

2 stops29h 20m

Chicago O'Hare Intl

Thu 5/7

3:00 pm-6:10 pm

2 stops20h 10m

$693

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Mon 4/27

6:30 am-6:36 pm

2 stops19h 06m

Chicago Midway

Mon 5/4

1:24 pm-11:30 am

2 stops15h 06m

$694

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sat 4/18

6:55 am-7:52 pm

2 stops19h 57m

Chicago O'Hare Intl

Sat 4/25

1:29 pm-12:10 pm

2 stops15h 41m

$711

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 5/18

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Mon 5/25

7:15 pm-7:05 pm

1 stop16h 50m

$777

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 4/22

6:30 am-6:13 pm

2 stops18h 43m

Chicago O'Hare Intl

Wed 5/27

2:00 pm-12:10 pm

2 stops15h 10m

$806

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Wed 4/22

6:30 am-6:36 pm

2 stops19h 06m

Chicago Midway

Wed 5/27

1:22 pm-12:10 pm

2 stops15h 48m

$806

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/1

11:25 am-6:35 pm

2 stops38h 10m

Chicago O'Hare Intl

Thu 5/7

3:00 pm-6:15 pm

1 stop20h 15m

$807

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4
  • 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

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 $396). Flying from Florence to Chicago in February is currently the most expensive (average of $786). 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.

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 April 3, 2026.
Get a feel of what it's like to fly with United Airlines 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
9,538 reviews

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

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
9,538 reviews
United Airlines
7.4
Good
9,538 reviews

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

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 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 $677, Delta can have you in Chicago from Florence in 15h. There are 4680 mi between Florence and Chicago.

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

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $445. However, be on the lookout for offers from British Airways 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 $396). Flying from Florence to Chicago in February is currently the most expensive (average of $786). 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
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Hammond
Porter
Benton Harbor

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