$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
Round-trip
1 adult, Economy
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Find cheap flights from Florence to Chicago with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Florence to ChicagoExplore 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.
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![Air Serbia logo]()
$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![ITA Airways logo]()
$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![British Airways logo]()
$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![British Airways logo]()
$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![British Airways logo]()
$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![British Airways logo]()
$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![Air Canada logo]()
$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![Delta logo]()
$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![Delta logo]()
$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![Delta logo]()
$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![Delta logo]()
$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![Delta logo]()
$918
Best flights from Florence to ChicagoDiscover 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 June 8, 2026.
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 June 8, 2026.
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 11/123:20 pm
FLR
- ORD
1 stop29h 30m
British Airways
Mon 11/166:50 pm
ORD
- FLR
1 stop12h 45m
British Airways
Deal found 6/6![British Airways logo]()
$699
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:30 am
FLR
- ORD
2 stops17h 58m
United Airlines
Mon 11/164:10 pm
ORD
- FLR
2 stops14h 40m
United Airlines
Deal found 6/7![United Airlines logo]()
$815
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![Delta logo]()
$831
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:20 pm
FLR
- ORD
1 stop34h 50m
Scandinavian Airlines
Mon 9/77:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Deal found 6/3![Scandinavian Airlines logo]()
$837
This oojo deal was found by Cheapflights users on 6/8. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Mon 7/273:00 pm
ORD
- FLR
1 stop12h 35m
ITA Airways
Deal found 6/8![ITA Airways logo]()
$850
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:40 pm
FLR
- ORD
1 stop32h 35m
KLM
Wed 9/24:50 pm
ORD
- FLR
1 stop19h 10m
KLM
Deal found 6/6![KLM logo]()
$976
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![British Airways logo]()
$702
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![Delta logo]()
$885
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:20 pm
FLR
- ORD
2 stops33h 19m
Scandinavian Airlines
Thu 8/207:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Deal found 6/6![Scandinavian Airlines logo]()
$974
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![Delta logo]()
$918
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.
Thu 8/66:30 am
FLR
- MDW
2 stops19h 03m
Delta
Fri 8/287:25 pm
MDW
- FLR
2 stops14h 25m
Delta
Deal found 6/7![Delta logo]()
$1,000
This Delta deal was found by Cheapflights users on 6/5. 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 7/1511:20 am
FLR
- ORD
2 stops19h 33m
Delta
Mon 7/273:19 pm
ORD
- FLR
2 stops16h 06m
Delta
Deal found 6/5![Delta logo]()
$1,022
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 7/26:30 am
FLR
- MDW
2 stops19h 01m
Delta
Thu 7/91:18 pm
MDW
- FLR
2 stops15h 12m
Delta
Deal found 6/3![Delta logo]()
$1,033
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.
Wed 8/56:30 am
FLR
- MDW
2 stops18h 31m
Delta
Wed 9/27:25 pm
MDW
- FLR
2 stops16h 35m
Delta
Deal found 6/6![Delta logo]()
$1,044
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.
Sun 7/196:30 am
FLR
- MDW
2 stops18h 55m
Delta
Sat 7/251:49 pm
MDW
- FLR
2 stops15h 21m
Delta
Deal found 6/3![Delta logo]()
$1,092
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.
Thu 6/186:30 am
FLR
- MDW
2 stops18h 48m
Delta
Wed 6/241:26 pm
MDW
- FLR
2 stops15h 44m
Delta
Deal found 6/7![Delta logo]()
$1,769
Last-minute flights from Florence to ChicagoDiscover last-minute flight deals from Florence to Chicago. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Florence to Chicago. Data last updated June 8, 2026 and is based on user searches.
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/113:30 pm
FLR
- ORD
1 stop28h 40m
ITA Airways
Wed 6/173:00 pm
ORD
- FLR
1 stop20h 15m
ITA Airways
Deal found 6/4![ITA Airways logo]()
$782
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:30 am
FLR
- MDW
2 stops16h 46m
Delta
Wed 6/176:58 pm
MDW
- FLR
2 stops17h 02m
Delta
Deal found 6/4![Delta logo]()
$936
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![ITA Airways logo]()
$678
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.
Mon 6/156:30 am
FLR
- MDW
2 stops18h 48m
Delta
Sun 6/211:26 pm
MDW
- FLR
2 stops15h 44m
Delta
Deal found 6/6![Delta logo]()
$965
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:25 am
FLR
- ORD
1 stop13h 45m
ITA Airways
Tue 6/233:00 pm
ORD
- FLR
1 stop16h 45m
ITA Airways
Deal found 6/7![ITA Airways logo]()
$778
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:05 am
FLR
- ORD
2 stops20h 54m
Multiple Airlines
Mon 7/275:00 pm
ORD
- FLR
1 stop11h 30m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$790
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.
Wed 7/157:05 am
FLR
- ORD
1 stop18h 10m
British Airways
Mon 7/279:15 pm
ORD
- FLR
1 stop18h 05m
British Airways
Deal found 6/7![British Airways logo]()
$800
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![Air Serbia logo]()
$674
This Iberia 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:45 am
FLR
- ORD
1 stop14h 40m
Multiple Airlines
Tue 7/289:15 pm
ORD
- FLR
1 stop18h 05m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$791
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.
Tue 7/216:30 am
FLR
- MDW
2 stops18h 48m
Delta
Tue 7/281:18 pm
MDW
- FLR
2 stops15h 12m
Delta
Deal found 6/6![Delta logo]()
$1,019
This Iberia 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:45 am
FLR
- ORD
1 stop14h 40m
Multiple Airlines
Thu 8/207:05 pm
ORD
- FLR
1 stop20h 15m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$793
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:05 pm
FLR
- ORD
1 stop31h 35m
TAP AIR PORTUGAL
Thu 8/207:50 pm
ORD
- FLR
1 stop15h 10m
TAP AIR PORTUGAL
Deal found 6/7![TAP AIR PORTUGAL logo]()
$795
One-way flights from Florence to ChicagoSearch for one-way flight options from Florence to Chicago. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
Search for one-way flight options from Florence to Chicago. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:55 pm
FLR
- ORD
3 stops50h 55m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$432
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:25 am
FLR
- ORD
3 stops42h 25m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$435
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:20 pm
FLR
- MDW
3 stops45h 20m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$437
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:45 pm
FLR
- ORD
3 stops36h 05m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:55 am
FLR
- ORD
3 stops41h 55m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$456
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/179:10 am
FLR
- ORD
2 stops34h 30m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$458
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:55 am
FLR
- ORD
3 stops41h 55m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:45 pm
FLR
- ORD
3 stops36h 05m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/48:40 pm
FLR
- ORD
3 stops28h 10m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$484
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:55 am
FLR
- MDW
3 stops57h 45m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$485
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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.
Fri 8/217:05 am
FLR
- ORD
1 stop15h 50m
British Airways
Deal found 6/8![British Airways logo]()
$491
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:05 pm
FLR
- MDW
3 stops50h 30m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$498
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 |
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
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
Showing 1-10 of 37 resultsSorted by cheapest first
- 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.
FLR-CHI
FLR-ORD
FLR-MDW
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
FLR-CHI
FLR-ORD
FLR-MDW
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
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Overall
7.4
Food
6.6
Crew
8.1
Boarding
7.7
Comfort
7.3
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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