$405+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
FLR ā CHI
Aug 16 ā Aug 231
Round-trip
1 adult, Economy
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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 July 17, 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 July 17, 2026.
This lastminute.com deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure lastminute.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/36:25 am
FLR
- ORD
1 stop13h 45m
ITA Airways
Tue 9/83:00 pm
ORD
- FLR
1 stop12h 40m
ITA Airways
Deal found 7/13![ITA Airways logo]()
$551
This ITA Airways deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure ITA Airways is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 9/27:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Sun 9/63:00 pm
ORD
- FLR
1 stop24h 40m
ITA Airways
Deal found 7/14![ITA Airways logo]()
$596
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/312:20 pm
FLR
- ORD
1 stop34h 50m
Scandinavian Airlines
Tue 9/87:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Deal found 7/17![Scandinavian Airlines logo]()
$631
This Gotogate deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Gotogate is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/227:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Sun 8/303:00 pm
ORD
- FLR
1 stop20h 15m
ITA Airways
Deal found 7/13![ITA Airways logo]()
$656
This Ticket deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Ticket is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/37:05 am
FLR
- ORD
1 stop15h 50m
British Airways
Tue 9/812:39 pm
ORD
- FLR
2 stops26h 41m
British Airways
Deal found 7/13![British Airways logo]()
$745
This Kissandfly.com deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kissandfly.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/36:45 am
FLR
- ORD
1 stop14h 40m
Multiple Airlines
Mon 9/74:55 pm
ORD
- FLR
1 stop19h 40m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$749
This Kissandfly.com deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kissandfly.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 11/46:50 am
FLR
- ORD
1 stop15h 05m
Multiple Airlines
Wed 11/115:40 pm
ORD
- FLR
1 stop16h 10m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$755
This Delta deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 11/46:40 am
FLR
- MDW
2 stops18h 25m
Delta
Wed 11/1110:35 am
MDW
- FLR
2 stops15h 25m
Delta
Deal found 7/17![Delta logo]()
$843
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/36:30 am
FLR
- MDW
2 stops19h 03m
Delta
Tue 9/85:45 pm
MDW
- FLR
2 stops16h 30m
Delta
Deal found 7/13![Delta logo]()
$857
This Delta deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/36:30 am
FLR
- MDW
2 stops18h 31m
Delta
Mon 9/76:42 pm
MDW
- FLR
2 stops15h 08m
Delta
Deal found 7/17![Delta logo]()
$871
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 12/226:40 am
FLR
- MDW
2 stops16h 45m
Delta
Sat 1/91:05 pm
MDW
- FLR
2 stops15h 20m
Delta
Deal found 7/13![Delta logo]()
$931
This Air France deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Air France is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 12/226:40 am
FLR
- MDW
2 stops16h 42m
Multiple Airlines
Fri 1/81:05 pm
MDW
- FLR
2 stops15h 20m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$941
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 July 17, 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 July 17, 2026.
This ITA Airways deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure ITA Airways is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 9/27:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Sun 9/63:00 pm
ORD
- FLR
1 stop24h 40m
ITA Airways
Deal found 7/14![ITA Airways logo]()
$596
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/36:30 am
FLR
- ORD
2 stops17h 27m
United Airlines
Mon 9/77:05 pm
ORD
- FLR
1 stop12h 05m
United Airlines
Deal found 7/17![United Airlines logo]()
$817
This Delta deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 11/46:40 am
FLR
- MDW
2 stops18h 25m
Delta
Wed 11/1110:35 am
MDW
- FLR
2 stops15h 25m
Delta
Deal found 7/17![Delta logo]()
$843
This Mytrip deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Mytrip is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/225:10 pm
FLR
- ORD
3 stops29h 50m
Multiple Airlines
Sun 8/306:00 pm
ORD
- FLR
2 stops22h 00m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$852
This KLM deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure KLM is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 12/216:40 am
FLR
- ORD
1 stop14h 45m
KLM
Sat 1/96:25 pm
ORD
- FLR
1 stop13h 00m
KLM
Deal found 7/13![KLM logo]()
$940
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/31:50 pm
FLR
- ORD
1 stop13h 05m
United Airlines
Tue 9/87:05 pm
ORD
- FLR
1 stop12h 05m
United Airlines
Deal found 7/14![United Airlines logo]()
$845
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/36:30 am
FLR
- MDW
2 stops19h 03m
Delta
Tue 9/85:45 pm
MDW
- FLR
2 stops16h 30m
Delta
Deal found 7/13![Delta logo]()
$857
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 12/236:30 am
FLR
- ORD
2 stops20h 05m
United Airlines
Sat 1/97:00 am
ORD
- FLR
2 stops22h 35m
United Airlines
Deal found 7/13![United Airlines logo]()
$929
This Delta deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 8/66:30 am
FLR
- ORD
1 stop14h 45m
Delta
Fri 8/285:20 pm
ORD
- FLR
2 stops16h 55m
Delta
Deal found 7/16![Delta logo]()
$945
This KLM deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure KLM is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 12/216:40 am
FLR
- MDW
2 stops16h 42m
Multiple Airlines
Thu 1/75:59 pm
MDW
- FLR
2 stops13h 26m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$1,040
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 12/2011:25 am
FLR
- ORD
1 stop34h 00m
Delta
Sat 1/96:10 pm
ORD
- FLR
2 stops18h 40m
Delta
Deal found 7/13![Delta logo]()
$949
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 12/236:40 am
FLR
- MDW
2 stops16h 42m
Delta
Sat 1/91:00 pm
MDW
- FLR
2 stops15h 25m
Delta
Deal found 7/14![Delta logo]()
$953
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 12/226:40 am
FLR
- MDW
2 stops16h 42m
Delta
Sat 1/91:00 pm
MDW
- FLR
2 stops15h 25m
Delta
Deal found 7/14![Delta logo]()
$953
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 12/226:40 am
FLR
- MDW
2 stops16h 42m
Delta
Fri 1/81:00 pm
MDW
- FLR
2 stops15h 25m
Delta
Deal found 7/14![Delta logo]()
$953
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 12/206:50 am
FLR
- MDW
2 stops16h 32m
Delta
Sat 1/91:00 pm
MDW
- FLR
2 stops15h 25m
Delta
Deal found 7/14![Delta logo]()
$971
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 12/206:50 am
FLR
- MDW
2 stops17h 00m
Delta
Thu 1/710:35 am
MDW
- FLR
2 stops17h 50m
Delta
Deal found 7/13![Delta logo]()
$1,034
This Delta deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/226:30 am
FLR
- MDW
2 stops18h 31m
Delta
Sun 8/307:25 pm
MDW
- FLR
2 stops14h 25m
Delta
Deal found 7/15![Delta logo]()
$1,219
Last-minute flights from Florence to ChicagoDiscover last-minute flight deals from Florence to Chicago. Data last updated July 17, 2026 and is based on user searches.
Discover last-minute flight deals from Florence to Chicago. Data last updated July 17, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure oojo is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 7/227:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Thu 8/203:00 pm
ORD
- FLR
1 stop20h 15m
ITA Airways
Deal found 7/14![ITA Airways logo]()
$778
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/26:55 am
FLR
- MDW
2 stops18h 30m
Delta
Sat 8/81:25 pm
MDW
- FLR
2 stops15h 45m
Delta
Deal found 7/14![Delta logo]()
$1,370
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 8/66:30 am
FLR
- MDW
2 stops19h 03m
Delta
Fri 8/281:25 pm
MDW
- FLR
2 stops15h 45m
Delta
Deal found 7/14![Delta logo]()
$1,333
This Justfly.com deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Justfly.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/157:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Sun 8/233:00 pm
ORD
- FLR
1 stop24h 40m
ITA Airways
Deal found 7/13![ITA Airways logo]()
$788
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/156:30 am
FLR
- MDW
2 stops18h 31m
Delta
Sun 8/236:42 pm
MDW
- FLR
2 stops15h 08m
Delta
Deal found 7/13![Delta logo]()
$1,022
This Gotogate deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Gotogate is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/227:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Sun 8/303:00 pm
ORD
- FLR
1 stop20h 15m
ITA Airways
Deal found 7/13![ITA Airways logo]()
$656
This Expedia deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Expedia is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/2210:00 pm
FLR
- ORD
2 stops27h 15m
Iberia
Sun 8/304:55 pm
ORD
- FLR
1 stop23h 10m
Iberia
Deal found 7/15![Iberia logo]()
$843
This Mytrip deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Mytrip is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/225:10 pm
FLR
- ORD
3 stops29h 50m
Multiple Airlines
Sun 8/306:00 pm
ORD
- FLR
2 stops22h 00m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$852
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/226:30 am
FLR
- ORD
2 stops20h 22m
United Airlines
Sun 8/303:55 pm
ORD
- FLR
2 stops15h 15m
United Airlines
Deal found 7/14![United Airlines logo]()
$853
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/226:30 am
FLR
- MDW
2 stops18h 31m
Delta
Sun 8/307:25 pm
MDW
- FLR
2 stops14h 25m
Delta
Deal found 7/13![Delta logo]()
$1,210
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/296:30 am
FLR
- ORD
2 stops33h 43m
United Airlines
Sat 12/198:50 pm
ORD
- FLR
2 stops36h 40m
United Airlines
Deal found 7/15![United Airlines logo]()
$823
This Delta deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/296:30 am
FLR
- MDW
2 stops18h 31m
Delta
Sat 12/199:30 am
MDW
- FLR
2 stops18h 10m
Delta
Deal found 7/15![Delta logo]()
$1,534
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 July 17, 2026.
Search for one-way flight options from Florence to Chicago. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
This Expedia deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Expedia is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 9/46:45 am
FLR
- ORD
1 stop14h 40m
Iberia
Deal found 7/16![Iberia logo]()
$405
This Expedia deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Expedia is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 9/116:45 am
FLR
- ORD
1 stop14h 40m
Iberia
Deal found 7/17![Iberia logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 9/19:00 am
FLR
- ORD
3 stops39h 50m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$415
This Travelocity deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Travelocity is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 10/2811:30 am
FLR
- ORD
1 stop34h 25m
Iberia
Deal found 7/13![Iberia logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 9/46:55 am
FLR
- ORD
3 stops44h 13m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 9/26:25 am
FLR
- ORD
3 stops42h 25m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 10/196:55 am
FLR
- ORD
3 stops41h 55m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$448
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 10/186:25 am
FLR
- ORD
3 stops42h 50m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 10/286:45 am
FLR
- ORD
2 stops39h 10m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 9/46:55 am
FLR
- MDW
3 stops46h 52m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 10/1912:30 pm
FLR
- MDW
3 stops29h 28m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Kiwi.com is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/116:25 am
FLR
- MDW
3 stops58h 20m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$534
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 July 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $551 (lastminute.com) |
One-way from | $405 (Expedia) |
Popular in | April |
Cheapest in | October |
Average price | $805 |
Cheapflights Fare Finder
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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 July 17, 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
Wed 9/2
7:00 pm-1:10 pm
1 stop25h 10m
Chicago O'Hare Intl
Sun 9/6
3:00 pm-10:40 pm
1 stop24h 40m
$596
FlorenceChicago
FLR - ORD
FLRORD
Florence Peretola
Thu 9/3
6:30 am-4:57 pm
2 stops17h 27m
Chicago O'Hare Intl
Mon 9/7
7:05 pm-2:10 pm
1 stop12h 05m
$817
FlorenceChicago
FLR - MDW
FLRMDW
Florence Peretola
Wed 11/4
6:40 am-6:05 pm
2 stops18h 25m
Chicago Midway
Wed 11/11
10:35 am-9:00 am
2 stops15h 25m
$843
Quickest round-trip
FlorenceChicago
FLR - ORD
FLRORD
Florence Peretola
Thu 9/3
1:50 pm-7:55 pm
1 stop13h 05m
Chicago O'Hare Intl
Tue 9/8
7:05 pm-2:10 pm
1 stop12h 05m
$845
FlorenceChicago
FLR - ORD
FLRORD
Florence Peretola
Sat 8/22
5:10 pm-4:00 pm
3 stops29h 50m
Chicago O'Hare Intl
Sun 8/30
6:00 pm-11:00 pm
2 stops22h 00m
$852
FlorenceChicago
FLR - MDW
FLRMDW
Florence Peretola
Thu 9/3
6:30 am-6:33 pm
2 stops19h 03m
Chicago Midway
Tue 9/8
5:45 pm-5:15 pm
2 stops16h 30m
$857
FlorenceChicago
FLR - ORD
FLRORD
Florence Peretola
Wed 12/23
6:30 am-7:35 pm
2 stops20h 05m
Chicago O'Hare Intl
Sat 1/9
7:00 am-12:35 pm
2 stops22h 35m
$929
FlorenceChicago
FLR - ORD
FLRORD
Florence Peretola
Mon 12/21
6:40 am-2:25 pm
1 stop14h 45m
Chicago O'Hare Intl
Sat 1/9
6:25 pm-2:25 pm
1 stop13h 00m
$940
FlorenceChicago
FLR - ORD
FLRORD
Florence Peretola
Thu 8/6
6:30 am-2:15 pm
1 stop14h 45m
Chicago O'Hare Intl
Fri 8/28
5:20 pm-5:15 pm
2 stops16h 55m
$945
FlorenceChicago
FLR - ORD
FLRORD
Florence Peretola
Sun 12/20
11:25 am-2:25 pm
1 stop34h 00m
Chicago O'Hare Intl
Sat 1/9
6:10 pm-7:50 pm
2 stops18h 40m
$949
Showing 1-10 of 36 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, October is the cheapest month in which you can book a flight from Florence to Chicago (average of $581). 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 July 17, 2026.
Get a feel of what it's like to fly with United Airlines and ITA Airways 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.
Comfort
7.3
Boarding
7.7
Food
6.6
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Comfort
7.3
Boarding
7.7
Food
6.6
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Comfort
7.3
Boarding
7.7
Food
6.6
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
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
Valparaiso
Hammond
Saint Joseph
Porter
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