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$392+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
May 19 — May 261
Tue 5/19
Tue 5/26
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 19, 2026.

This lol.travel deal was found by Cheapflights users on 4/17. 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 5/111:20 am
FLR
-
ORD
1 stop32h 50m
ITA Airways
Thu 5/73:00 pm
ORD
-
FLR
1 stop12h 35m
ITA Airways
Deal found 4/17$530
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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.
Wed 10/217:05 am
FLR
-
ORD
1 stop13h 45m
Multiple Airlines
Mon 10/266:40 pm
ORD
-
FLR
1 stop19h 05m
Multiple Airlines
Deal found 4/16$675
This British Airways deal was found by Cheapflights users on 4/18. 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.
Fri 5/17:05 am
FLR
-
ORD
1 stop18h 10m
British Airways
Thu 5/75:00 pm
ORD
-
FLR
1 stop22h 20m
British Airways
Deal found 4/18$676
This British Airways deal was found by Cheapflights users on 4/15. 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
Sun 11/159:45 pm
ORD
-
FLR
1 stop33h 50m
British Airways
Deal found 4/15$677
This Priceline deal was found by Cheapflights users on 4/16. 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 10/216:45 am
FLR
-
ORD
1 stop14h 40m
Iberia
Mon 10/267:50 pm
ORD
-
FLR
2 stops17h 55m
Iberia
Deal found 4/16$680
This Gotogate deal was found by Cheapflights users on 4/15. 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 6/246:25 am
FLR
-
ORD
1 stop13h 45m
ITA Airways
Tue 7/213:00 pm
ORD
-
FLR
1 stop24h 40m
ITA Airways
Deal found 4/15$688
This Mytrip deal was found by Cheapflights users on 4/14. 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 5/11:00 pm
FLR
-
ORD
2 stops31h 10m
Multiple Airlines
Thu 5/73:00 pm
ORD
-
FLR
2 stops24h 30m
Multiple Airlines
Deal found 4/14$708
This Expedia deal was found by Cheapflights users on 4/17. 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.
Fri 5/11:05 pm
FLR
-
ORD
2 stops14h 35m
KLM
Thu 5/75:10 pm
ORD
-
FLR
1 stop22h 35m
KLM
Deal found 4/17$713
This Iberia deal was found by Cheapflights users on 4/16. 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.
Thu 11/126:55 am
FLR
-
ORD
1 stop15h 00m
Iberia
Sun 11/155:40 pm
ORD
-
FLR
1 stop16h 10m
Iberia
Deal found 4/16$715
This Delta deal was found by Cheapflights users on 4/14. 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 5/86:30 am
FLR
-
MDW
2 stops19h 03m
Delta
Wed 5/136:36 pm
MDW
-
FLR
2 stops17h 24m
Delta
Deal found 4/14$789
This Delta deal was found by Cheapflights users on 4/17. 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 5/226:40 am
FLR
-
MDW
2 stops18h 53m
Delta
Tue 5/261:22 pm
MDW
-
FLR
2 stops15h 08m
Delta
Deal found 4/17$851
This Delta deal was found by Cheapflights users on 4/14. 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 5/112:25 pm
FLR
-
MDW
2 stops17h 03m
Delta
Thu 5/76:36 pm
MDW
-
FLR
2 stops17h 24m
Delta
Deal found 4/14$890

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 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$530
(lol.travel)

One-way from

$392
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$907
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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 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 19, 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

Fri 5/1

11:20 am-1:10 pm

1 stop32h 50m

Chicago O'Hare Intl

Thu 5/7

3:00 pm-2:45 pm

1 stop16h 45m

$544

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/1

7:05 am-6:15 pm

1 stop18h 10m

Chicago O'Hare Intl

Thu 5/7

5:00 pm-10:20 pm

1 stop22h 20m

$676

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Fri 5/8

6:30 am-6:33 pm

2 stops19h 03m

Chicago Midway

Wed 5/13

6:36 pm-7:00 pm

2 stops17h 24m

$789

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/1

12:25 pm-11:59 pm

2 stops18h 34m

Chicago O'Hare Intl

Thu 5/7

5:10 pm-5:15 pm

1 stop17h 05m

$790

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/8

6:30 am-2:15 pm

1 stop14h 45m

Chicago O'Hare Intl

Wed 5/13

7:00 pm-7:00 pm

2 stops17h 00m

$828

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/22

6:30 am-5:02 pm

2 stops17h 32m

Chicago O'Hare Intl

Tue 5/26

1:18 pm-11:00 am

2 stops14h 42m

$837

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Fri 5/22

6:40 am-6:33 pm

2 stops18h 53m

Chicago Midway

Tue 5/26

1:22 pm-11:30 am

2 stops15h 08m

$851
Quickest round-trip

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 5/1

6:30 am-3:43 pm

2 stops16h 13m

Chicago O'Hare Intl

Thu 5/7

3:50 pm-2:10 pm

1 stop15h 20m

$868

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Fri 5/1

12:25 pm-10:28 pm

2 stops17h 03m

Chicago Midway

Thu 5/7

6:36 pm-7:00 pm

2 stops17h 24m

$890

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 8/4

7:40 pm-2:30 pm

1 stop25h 50m

Chicago O'Hare Intl

Mon 8/31

4:50 pm-4:50 pm

1 stop17h 00m

$902

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 31 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 $793). 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 19, 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
9,604 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,604 reviews
United Airlines
7.4
Good
9,604 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 $676, ITA Airways can have you in Chicago from Florence in 18h 10m. There are 4680 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 $793). 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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Alternative routes for Florence to Chicago

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