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Cheap flights from Chicago to Florence from $259

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Florence departing on 10/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Florence (CHI-FLR)

Cheap round-trip flights

Logo
6:00 pm - 9:25 pmORD-FLR
20h 25m2 stops
Logo
11:20 am - 4:10 pmFLR-ORD
35h 50m3 stops
$729
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Thu, Oct 9 - Thu, Oct 16
ITA Airways Logo
3:00 pm - 10:35 amORD-FLR
12h 35m1 stop
ITA Airways Logo
6:25 am - 1:10 pmFLR-ORD
13h 45m1 stop
$730ITA Airways
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Mon, Sep 22 - Fri, Sep 26
Delta Logo
6:23 pm - 5:20 pmMDW-FLR
15h 57m2 stops
Delta Logo
6:30 am - 6:25 pmFLR-MDW
18h 55m2 stops
$732Delta
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Tue, Oct 14 - Tue, Oct 21
ITA Airways Logo
3:00 pm - 10:35 amORD-FLR
12h 35m1 stop
ITA Airways Logo
6:25 am - 1:10 pmFLR-ORD
13h 45m1 stop
$732ITA Airways
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Sun, Sep 7 - Fri, Sep 19
United Airlines Logo
6:50 pm - 1:45 pmORD-FLR
11h 55m1 stop
United Airlines Logo
6:40 am - 7:55 pmFLR-ORD
20h 15m1 stop
$742United Airlines
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Mon, Jan 26 - Sat, May 16
United Airlines Logo
7:30 am - 1:45 pmORD-FLR
23h 15m2 stops
United Airlines Logo
6:40 am - 12:55 pmFLR-ORD
13h 15m1 stop
$747United Airlines
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Mon, Jan 26 - Sat, May 16
Lufthansa Logo
3:35 pm - 2:55 pmORD-FLR
16h 20m1 stop
Lufthansa Logo
10:20 am - 7:55 pmFLR-ORD
16h 35m1 stop
$749Lufthansa
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Sun, Oct 5 - Tue, Oct 14
Delta Logo
10:25 am - 9:05 amORD-FLR
15h 40m2 stops
Delta Logo
9:50 am - 4:10 pmFLR-ORD
12h 20m1 stop
$753Delta
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Thu, Oct 23 - Wed, Oct 29
SWISS Logo
7:05 pm - 2:05 pmORD-FLR
12h 00m1 stop
SWISS Logo
6:55 pm - 5:20 pmFLR-ORD
28h 25m1 stop
$759SWISS
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Thu, Oct 23 - Tue, Oct 28
Lufthansa Logo
10:30 pm - 10:40 pmORD-FLR
17h 10m1 stop
Lufthansa Logo
8:15 am - 9:30 pmFLR-ORD
20h 15m2 stops
$772Lufthansa
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Wed, Sep 24 - Fri, Oct 3

United Airlines flights from Chicago to Florence

Our best United Airlines deals on Chicago to Florence flight tickets
United Airlines
Jan 26
ORD6:50 pmChicago O'Hare Intl
11h 55m
1 stop
FLR1:45 pmFlorence Peretola
May 16
FLR6:40 amFlorence Peretola
20h 15m
1 stop
ORD7:55 pmChicago O'Hare Intl
$742
Find similar
United Airlines
Jan 26
ORD7:30 amChicago O'Hare Intl
23h 15m
2 stops
FLR1:45 pmFlorence Peretola
May 16
FLR6:40 amFlorence Peretola
13h 15m
1 stop
ORD12:55 pmChicago O'Hare Intl
$747
Find similar
United Airlines
Oct 23
ORD10:40 amChicago O'Hare Intl
17h 05m
2 stops
FLR10:45 amFlorence Peretola
Oct 31
FLR6:30 amFlorence Peretola
17h 49m
2 stops
ORD6:19 pmChicago O'Hare Intl
$754
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KLM flights from Chicago to Florence

Our best KLM deals on Chicago to Florence flight tickets
KLM
Jan 2
ORD5:20 pmChicago O'Hare Intl
14h 05m
1 stop
FLR2:25 pmFlorence Peretola
Jan 17
FLR6:40 amFlorence Peretola
14h 40m
1 stop
ORD2:20 pmChicago O'Hare Intl
$733
Find similar
KLM
Oct 11
ORD5:10 pmChicago O'Hare Intl
17h 10m
1 stop
FLR5:20 pmFlorence Peretola
Oct 23
FLR6:20 pmFlorence Peretola
27h 40m
1 stop
ORD3:00 pmChicago O'Hare Intl
$761
Find similar
KLM
Dec 23
ORD5:20 pmChicago O'Hare Intl
22h 35m
1 stop
FLR10:55 pmFlorence Peretola
Dec 31
FLR9:50 amFlorence Peretola
12h 20m
1 stop
ORD3:10 pmChicago O'Hare Intl
$780
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Florence 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, momondo users made 832,500 searches. Data last updated August 25, 2025.
Use the filters below to find and compare flights from Chicago to Florence that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Thu 10/9

6:00 pm-9:25 pm

2 stops20h 25m

Florence Peretola

Thu 10/16

11:20 am-4:10 pm

3 stops35h 50m

$729

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Mon 9/22

3:00 pm-10:35 am

1 stop12h 35m

Florence Peretola

Fri 9/26

6:25 am-1:10 pm

1 stop13h 45m

$730

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Tue 10/14

6:23 pm-5:20 pm

2 stops15h 57m

Florence Peretola

Tue 10/21

6:30 am-6:25 pm

2 stops18h 55m

$732

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sun 9/7

3:00 pm-10:35 am

1 stop12h 35m

Florence Peretola

Fri 9/19

6:25 am-1:10 pm

1 stop13h 45m

$732

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Mon 1/26

6:50 pm-1:45 pm

1 stop11h 55m

Florence Peretola

Sat 5/16

6:40 am-7:55 pm

1 stop20h 15m

$742

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Mon 1/26

7:30 am-1:45 pm

2 stops23h 15m

Florence Peretola

Sat 5/16

6:40 am-12:55 pm

1 stop13h 15m

$747

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sun 10/5

3:35 pm-2:55 pm

1 stop16h 20m

Florence Peretola

Tue 10/14

10:20 am-7:55 pm

1 stop16h 35m

$749

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Thu 10/23

10:25 am-9:05 am

2 stops15h 40m

Florence Peretola

Wed 10/29

9:50 am-4:10 pm

1 stop12h 20m

$753

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Thu 10/23

7:05 pm-2:05 pm

1 stop12h 00m

Florence Peretola

Tue 10/28

6:55 pm-5:20 pm

1 stop28h 25m

$759

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 9/24

10:30 pm-10:40 pm

1 stop17h 10m

Florence Peretola

Fri 10/3

8:15 am-9:30 pm

2 stops20h 15m

$772

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Florence from

How to get the cheapest flight ticket from Chicago to Florence

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Florence?

What is the cheapest month to fly to Florence?

If you aren’t able to travel during the month of November, then book flights to Florence from Chicago during October instead. Flights to Florence in October, while not as cheap as those in November, still average around $765.

What is the cheapest day to depart on your flight to Florence?

On average, the least expensive day to fly to Florence from Chicago is on a Sunday. momondo users have found tickets for Sunday departures for as low as $1,011. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Florence on Friday is $1,251.

What is the cheapest time of day to depart on your flight to Florence?

Our data shows that the cheapest Chicago to Florence flights are usually those with departure times in the morning. Our users have found flights to Florence in the morning for as low as $908. Flights to Florence are more costly at noon, with an average ticket price of $1,523. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

How far in advance should I book a flight to Florence?

You are more likely to see cheaper flights to Florence from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Florence for around $1,040 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florence from Chicago for as low as $861 on momondo.

Can stopping save me money on Chicago to Florence flights?

You could potentially save up to 42% on your flight if you consider stops on a Chicago to Florence flight.

When to book flights from Chicago to Florence

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Florence according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Florence (CHI to FLR) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Florence

Direct flights

None
There are no direct flights from Chicago to Florence. There are no popular flight routes from Chicago to Florence.
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  • How far is Chicago to Florence Peretola by plane?

    There are 4677.4 mi between Chicago and Florence Peretola. 11h 55m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to Florence Peretola Airport?

    Prices for flights from Chicago to Florence Peretola Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Florence Peretola Airport?

  • How old do you have to be to fly from Chicago to Florence Peretola Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Florence Peretola Airport.

  • What documentation or ID do you need to fly to Florence Peretola Airport?

    The travel and health documents you'll need for your trip to Florence Peretola Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Florence Peretola Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago to Florence?

Best airlines flying from Chicago to Florence

Compare and see reviews for airlines that fly from Chicago to Florence with momondo
Airline
Rating
Free Cancellation
Price
Scandinavian AirlinesPriceFrom $470Free CancellationRating
7.4
1,473 reviews
Search Scandinavian Airlines flights
KLMPriceFrom $491Free CancellationRating
7.8
1,388 reviews
Search KLM flights
Air FrancePriceFrom $594Free CancellationRating
7.4
1,469 reviews
Search Air France flights
LufthansaPriceFrom $630Free CancellationRating
6.8
7,359 reviews
Search Lufthansa flights
British AirwaysPriceFrom $647Free CancellationRating
6.7
7,305 reviews
Search British Airways flights
DeltaPriceFrom $699Free CancellationRating
7.9
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $704Free CancellationRating
7.4
8,940 reviews
Search United Airlines flights
SWISSPriceFrom $708Free CancellationRating
7.6
1,710 reviews
Search SWISS flights
IberiaPriceFrom $741Free CancellationRating
7.0
2,889 reviews
Search Iberia flights
ITA AirwaysPriceFrom $770Free CancellationRating
6.7
1,024 reviews
Search ITA Airways flights

Traveling to a place near Florence?

Book flights to Florence if you plan to visit one of these locations
Siena
San Gimignano
Prato
Pistoia
Montecatini Terme
Arezzo
Colle di Val d'Elsa
Fiesole
Poggibonsi
Impruneta
Greve in Chianti
Monteriggioni
Volterra

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Florence?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Florence. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Florence with flexible booking policies on momondo?

momondo does allow users to show only those flights to Florence from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Florence?

momondo helps you find the best flight between Chicago and Florence by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Florence right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Florence, momondo offers a useful price alert feature which will track prices for flights to Florence from Chicago and alert you when they change.

An easier way to manage your Florence trip

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