Chicago

$432+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Jul 8 — Jul 151
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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 June 8, 2026.

This Air Serbia deal was found by Cheapflights users on 6/4. 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 Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/198:40 pm
FLR
-
ORD
1 stop24h 50m
Air Serbia
Sat 7/2511:20 pm
ORD
-
FLR
1 stop13h 40m
Air Serbia
Deal found 6/4$674
This lol.travel deal was found by Cheapflights users on 6/6. 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.
Mon 6/157:00 pm
FLR
-
ORD
1 stop25h 10m
ITA Airways
Sun 6/213:00 pm
ORD
-
FLR
1 stop12h 40m
ITA Airways
Deal found 6/6$678
This British Airways deal was found by Cheapflights users on 6/7. 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 stop29h 30m
British Airways
Mon 11/164:06 pm
ORD
-
FLR
2 stops15h 29m
British Airways
Deal found 6/7$699
This British Airways deal was found by Cheapflights users on 6/6. 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 10/17:05 am
FLR
-
ORD
1 stop15h 50m
British Airways
Thu 11/1911:48 am
ORD
-
FLR
2 stops16h 57m
British Airways
Deal found 6/6$702
This Expedia deal was found by Cheapflights users on 6/3. 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.
Mon 8/317:05 am
FLR
-
ORD
1 stop15h 50m
British Airways
Fri 10/307:50 pm
ORD
-
FLR
1 stop16h 05m
British Airways
Deal found 6/3$705
This Booking.com deal was found by Cheapflights users on 6/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:05 am
FLR
-
ORD
1 stop18h 10m
British Airways
Sat 11/213:30 pm
ORD
-
FLR
2 stops20h 50m
British Airways
Deal found 6/6$738
This lol.travel deal was found by Cheapflights users on 6/6. 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 10/16:30 am
FLR
-
ORD
2 stops16h 21m
Air Canada
Sat 11/2112:00 pm
ORD
-
FLR
2 stops14h 40m
Air Canada
Deal found 6/6$749
This Delta deal was found by Cheapflights users on 6/6. 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 10/16:40 am
FLR
-
MDW
2 stops18h 53m
Delta
Sat 11/211:00 pm
MDW
-
FLR
2 stops16h 25m
Delta
Deal found 6/6$810
This Delta deal was found by Cheapflights users on 6/3. 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 8/316:30 am
FLR
-
MDW
2 stops18h 31m
Delta
Fri 10/3012:30 pm
MDW
-
FLR
2 stops16h 10m
Delta
Deal found 6/3$831
This Delta deal was found by Cheapflights users on 6/6. 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 10/16:40 am
FLR
-
MDW
2 stops18h 53m
Delta
Thu 11/1912:30 pm
MDW
-
FLR
2 stops15h 50m
Delta
Deal found 6/6$885
This Delta deal was found by Cheapflights users on 6/7. 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 8/56:30 am
FLR
-
MDW
2 stops19h 03m
Delta
Mon 8/317:25 pm
MDW
-
FLR
2 stops16h 35m
Delta
Deal found 6/7$909
This Delta deal was found by Cheapflights users on 6/3. 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 8/66:30 am
FLR
-
MDW
2 stops19h 03m
Delta
Mon 8/315:45 pm
MDW
-
FLR
2 stops16h 05m
Delta
Deal found 6/3$918

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 June 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$674
(Air Serbia)

One-way from

$432
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$948
Provider with most accurate pricing for Florence Peretola-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Florence Peretola-Chicago (CHI) flights.
From Florence Peretola to Chicago (CHI)
One-way flight from Florence Peretola to Chicago (CHI)
Highest demand for flights based on searches. 19% potential increase in price ($203 potential increase over avg. RT price).
Cheapest flight prices on average. 7% potential price decrease ($60 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 June 8, 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

Thu 11/12

3:20 pm-1:50 pm

1 stop29h 30m

Chicago O'Hare Intl

Mon 11/16

6:50 pm-2:35 pm

1 stop12h 45m

$699

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 10/1

7:05 am-3:55 pm

1 stop15h 50m

Chicago O'Hare Intl

Thu 11/19

11:48 am-11:45 am

2 stops16h 57m

$702
Quickest round-trip

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 11/12

6:30 am-5:28 pm

2 stops17h 58m

Chicago O'Hare Intl

Mon 11/16

4:10 pm-1:50 pm

2 stops14h 40m

$815

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Mon 8/31

6:30 am-6:01 pm

2 stops18h 31m

Chicago Midway

Fri 10/30

12:30 pm-10:40 am

2 stops16h 10m

$831

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 9/3

12:20 pm-4:10 pm

1 stop34h 50m

Chicago O'Hare Intl

Mon 9/7

7:15 pm-7:05 pm

1 stop16h 50m

$837

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 7/15

7:00 pm-1:10 pm

1 stop25h 10m

Chicago O'Hare Intl

Mon 7/27

3:00 pm-10:35 am

1 stop12h 35m

$850

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 10/1

6:40 am-6:33 pm

2 stops18h 53m

Chicago Midway

Thu 11/19

12:30 pm-11:20 am

2 stops15h 50m

$885

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 8/6

6:30 am-6:33 pm

2 stops19h 03m

Chicago Midway

Mon 8/31

5:45 pm-4:50 pm

2 stops16h 05m

$918

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 7/22

8:20 pm-10:39 pm

2 stops33h 19m

Chicago O'Hare Intl

Thu 8/20

7:15 pm-7:05 pm

1 stop16h 50m

$974

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Wed 8/5

12:40 pm-2:15 pm

1 stop32h 35m

Chicago O'Hare Intl

Wed 9/2

4:50 pm-7:00 pm

1 stop19h 10m

$976

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/7

Showing 1-10 of 37 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, February is the cheapest month in which you can book a flight from Florence to Chicago (average of $559). Flying from Florence to Chicago in April is currently the most expensive (average of $907). 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 June 8, 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.

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 $885, Air Serbia can have you in Chicago from Florence in 18h 53m. 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 American Airlines, with whom users have recently found tickets for as low as $445. However, be on the lookout for offers from Iberia and British Airways, 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, February is the cheapest month in which you can book a flight from Florence to Chicago (average of $559). Flying from Florence to Chicago in April is currently the most expensive (average of $907). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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