$328+ Cheap flights from Midway (MDW) to Italy
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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Aug 25 — Sep 11
Round-trip
1 adult, Economy
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Cheapest flights from Midway to ItalyExplore the most affordable flight options available from Midway to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 26, 2026.
Explore the most affordable flight options available from Midway to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 26, 2026.
This KLM deal was found by Cheapflights users on 7/23. 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.
Sun 8/910:54 am
MDW
- FCO
1 stop13h 41m
KLM
Tue 8/259:00 am
FCO
- MDW
1 stop16h 33m
KLM
Deal found 7/23![KLM logo]()
$723
This Delta deal was found by Cheapflights users on 7/22. 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 8/121:25 pm
MDW
- FCO
1 stop14h 35m
Delta
Wed 8/196:30 am
FCO
- MDW
2 stops18h 31m
Delta
Deal found 7/22![Delta logo]()
$731
This KLM deal was found by Cheapflights users on 7/23. 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.
Mon 8/1010:54 am
MDW
- VCE
1 stop15h 01m
KLM
Thu 8/2011:05 am
VCE
- MDW
1 stop18h 31m
KLM
Deal found 7/23![KLM logo]()
$731
This Delta deal was found by Cheapflights users on 7/23. 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 10/289:29 am
MDW
- FCO
1 stop18h 06m
Delta
Fri 11/66:10 am
FCO
- MDW
2 stops17h 29m
Delta
Deal found 7/23![Delta logo]()
$732
This KLM deal was found by Cheapflights users on 7/22. 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.
Mon 11/91:05 pm
MDW
- FCO
1 stop12h 10m
Multiple Airlines
Fri 11/1310:00 am
FCO
- MDW
1 stop15h 37m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$733
This Delta deal was found by Cheapflights users on 7/21. 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 8/111:51 pm
MDW
- VCE
2 stops14h 29m
Delta
Thu 8/2011:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/21![Delta logo]()
$735
This Ticket deal was found by Cheapflights users on 7/25. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:46 pm
MDW
- MXP
1 stop13h 39m
KLM
Wed 8/1911:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 7/25![KLM logo]()
$758
This Mytrip deal was found by Cheapflights users on 7/25. 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.
Tue 9/811:45 am
MDW
- FCO
2 stops15h 40m
Porter Airlines
Tue 9/1512:15 pm
FCO
- MDW
2 stops33h 20m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$758
This Delta deal was found by Cheapflights users on 7/25. 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 8/1712:46 pm
MDW
- VCE
1 stop13h 09m
Delta
Thu 8/2711:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/25![Delta logo]()
$762
This Delta deal was found by Cheapflights users on 7/23. 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 8/912:46 pm
MDW
- VCE
1 stop13h 09m
Delta
Thu 8/2011:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/23![Delta logo]()
$767
This Delta deal was found by Cheapflights users on 7/23. 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 8/121:25 pm
MDW
- VCE
2 stops14h 55m
Delta
Fri 8/2111:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/23![Delta logo]()
$771
This Trip.com deal was found by Cheapflights users on 7/21. 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.
Sun 8/96:05 am
MDW
- FCO
1 stop18h 30m
Multiple Airlines
Tue 8/259:00 am
FCO
- MDW
1 stop16h 33m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$773
Best flights from Midway to ItalyDiscover carefully curated flight deals from Midway to Italy that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 26, 2026.
Discover carefully curated flight deals from Midway to Italy that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 26, 2026.
This Delta deal was found by Cheapflights users on 7/25. 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 11/910:35 am
MDW
- FCO
1 stop14h 40m
Delta
Fri 11/136:10 am
FCO
- MDW
2 stops17h 40m
Delta
Deal found 7/25![Delta logo]()
$732
This Condor deal was found by Cheapflights users on 7/25. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:40 am
MDW
- MXP
2 stops33h 20m
Multiple Airlines
Tue 9/157:00 am
MXP
- MDW
2 stops20h 55m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$893
This Expedia deal was found by Cheapflights users on 7/24. 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.
Tue 9/84:30 pm
MDW
- BRI
2 stops21h 00m
KLM
Tue 9/156:30 am
BRI
- MDW
2 stops19h 03m
KLM
Deal found 7/24![KLM logo]()
$973
This Delta deal was found by Cheapflights users on 7/24. 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 8/1210:54 am
MDW
- VCE
1 stop15h 01m
Delta
Fri 8/2111:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/24![Delta logo]()
$762
This Delta deal was found by Cheapflights users on 7/21. 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 8/131:25 pm
MDW
- FCO
1 stop14h 35m
Delta
Fri 8/216:30 am
FCO
- MDW
2 stops19h 03m
Delta
Deal found 7/21![Delta logo]()
$781
This KLM deal was found by Cheapflights users on 7/26. 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.
Sat 8/151:51 pm
MDW
- PMO
2 stops15h 24m
Multiple Airlines
Mon 8/249:50 am
PMO
- MDW
2 stops19h 46m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$923
This Delta deal was found by Cheapflights users on 7/25. 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 10/281:27 pm
MDW
- FCO
1 stop14h 08m
Delta
Sat 11/76:10 am
FCO
- MDW
2 stops18h 50m
Delta
Deal found 7/25![Delta logo]()
$782
This KLM deal was found by Cheapflights users on 7/22. 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 8/51:25 pm
MDW
- NAP
2 stops14h 10m
KLM
Wed 8/199:05 am
NAP
- MDW
1 stop20h 31m
KLM
Deal found 7/22![KLM logo]()
$1,012
This Condor deal was found by Cheapflights users on 7/25. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
MDW
- VCE
2 stops21h 25m
Multiple Airlines
Sun 8/308:40 am
VCE
- MDW
2 stops21h 00m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$941
This Delta deal was found by Cheapflights users on 7/22. 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 11/91:00 pm
MDW
- BLQ
2 stops17h 55m
Delta
Thu 11/126:35 am
BLQ
- MDW
2 stops19h 02m
Delta
Deal found 7/22![Delta logo]()
$782
This KLM deal was found by Cheapflights users on 7/25. 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.
Sat 9/1911:35 am
MDW
- NAP
1 stop12h 30m
KLM
Wed 9/309:05 am
NAP
- MDW
1 stop20h 39m
KLM
Deal found 7/25![KLM logo]()
$1,054
This Delta deal was found by Cheapflights users on 7/22. 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 8/910:54 am
MDW
- MXP
1 stop15h 31m
Delta
Fri 8/2111:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 7/22![Delta logo]()
$796
This Air France deal was found by Cheapflights users on 7/25. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:37 pm
MDW
- BRI
2 stops15h 58m
Multiple Airlines
Tue 9/156:30 am
BRI
- MDW
2 stops19h 03m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$964
This Air France deal was found by Cheapflights users on 7/25. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:37 pm
MDW
- BLQ
2 stops13h 23m
Multiple Airlines
Tue 9/151:55 pm
BLQ
- MDW
2 stops15h 49m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$965
This Delta deal was found by Cheapflights users on 7/21. 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 8/261:25 pm
MDW
- FCO
1 stop14h 35m
Delta
Tue 9/86:30 am
FCO
- MDW
2 stops18h 49m
Delta
Deal found 7/21![Delta logo]()
$806
This KLM deal was found by Cheapflights users on 7/21. 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.
Tue 9/2910:48 am
MDW
- FCO
1 stop13h 47m
KLM
Sun 11/110:00 am
FCO
- MDW
1 stop15h 05m
KLM
Deal found 7/21![KLM logo]()
$1,085
This Delta deal was found by Cheapflights users on 7/23. 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 10/141:28 pm
MDW
- FCO
1 stop14h 32m
Delta
Thu 10/226:30 am
FCO
- MDW
2 stops17h 09m
Delta
Deal found 7/23![Delta logo]()
$806
This KLM deal was found by Cheapflights users on 7/26. 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 9/95:37 pm
MDW
- MXP
2 stops14h 08m
Multiple Airlines
Wed 9/1611:40 am
MXP
- MDW
1 stop18h 04m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$1,000
This KLM deal was found by Cheapflights users on 7/25. 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.
Sat 10/105:31 pm
MDW
- PMO
2 stops14h 34m
KLM
Mon 10/196:10 am
PMO
- MDW
2 stops18h 55m
KLM
Deal found 7/25![KLM logo]()
$1,107
This Delta deal was found by Cheapflights users on 7/22. 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.
Sat 12/56:30 pm
MDW
- MXP
2 stops32h 20m
Delta
Tue 12/811:00 am
MXP
- MDW
2 stops38h 37m
Delta
Deal found 7/22![Delta logo]()
$824
This Condor deal was found by Cheapflights users on 7/23. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:00 am
MDW
- MXP
2 stops22h 00m
Multiple Airlines
Mon 8/246:55 am
MXP
- MDW
2 stops22h 05m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$1,003
This KLM deal was found by Cheapflights users on 7/26. 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.
Thu 10/225:31 pm
MDW
- CTA
2 stops15h 14m
KLM
Sat 10/3110:15 am
CTA
- MDW
2 stops18h 18m
KLM
Deal found 7/26![KLM logo]()
$1,130
This Delta deal was found by Cheapflights users on 7/25. 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 12/1512:30 pm
MDW
- FCO
1 stop14h 45m
Delta
Fri 12/256:10 am
FCO
- MDW
2 stops17h 40m
Delta
Deal found 7/25![Delta logo]()
$831
This Air France deal was found by Cheapflights users on 7/23. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:15 pm
MDW
- CTA
2 stops15h 25m
Multiple Airlines
Thu 11/510:15 am
CTA
- MDW
2 stops19h 10m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$1,011
This Delta deal was found by Cheapflights users on 7/26. 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.
Sat 1/165:25 pm
MDW
- BLQ
2 stops16h 45m
Delta
Fri 1/226:35 am
BLQ
- MDW
2 stops17h 15m
Delta
Deal found 7/26![Delta logo]()
$832
This KLM deal was found by Cheapflights users on 7/26. 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.
Thu 10/225:31 pm
MDW
- CTA
2 stops15h 14m
KLM
Sun 11/16:00 am
CTA
- MDW
2 stops19h 05m
KLM
Deal found 7/26![KLM logo]()
$1,244
This Delta deal was found by Cheapflights users on 7/26. 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 1/1510:35 am
MDW
- BLQ
2 stops16h 10m
Delta
Fri 1/226:35 am
BLQ
- MDW
2 stops16h 50m
Delta
Deal found 7/26![Delta logo]()
$832
This Air France deal was found by Cheapflights users on 7/24. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/231:25 pm
MDW
- BRI
2 stops17h 55m
Multiple Airlines
Sun 8/306:30 am
BRI
- MDW
2 stops19h 03m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$1,145
This KLM deal was found by Cheapflights users on 7/26. 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 9/94:30 pm
MDW
- CTA
2 stops16h 15m
KLM
Wed 9/169:55 am
CTA
- MDW
2 stops19h 49m
KLM
Deal found 7/26![KLM logo]()
$1,277
This Delta deal was found by Cheapflights users on 7/25. 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 8/2312:46 pm
MDW
- VCE
1 stop13h 09m
Delta
Sun 8/306:00 am
VCE
- MDW
2 stops19h 33m
Delta
Deal found 7/25![Delta logo]()
$838
Last-minute flights from Midway to ItalyDiscover last-minute flight deals from Midway to Italy. Data last updated July 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Italy. Data last updated July 26, 2026 and is based on user searches.
This Ticket deal was found by Cheapflights users on 7/25. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:46 pm
MDW
- MXP
1 stop13h 39m
KLM
Wed 8/1911:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 7/25![KLM logo]()
$758
This KLM deal was found by Cheapflights users on 7/23. 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.
Sun 8/910:54 am
MDW
- FCO
1 stop13h 41m
KLM
Tue 8/259:00 am
FCO
- MDW
1 stop16h 33m
KLM
Deal found 7/23![KLM logo]()
$723
This Delta deal was found by Cheapflights users on 7/23. 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 8/912:46 pm
MDW
- VCE
1 stop13h 09m
Delta
Thu 8/2011:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/23![Delta logo]()
$767
This Trip.com deal was found by Cheapflights users on 7/21. 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.
Sun 8/96:05 am
MDW
- FCO
1 stop18h 30m
Multiple Airlines
Tue 8/259:00 am
FCO
- MDW
1 stop16h 33m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$773
This KLM deal was found by Cheapflights users on 7/23. 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.
Sun 8/96:42 pm
MDW
- VCE
2 stops15h 18m
KLM
Wed 8/266:00 am
VCE
- MDW
2 stops19h 33m
KLM
Deal found 7/23![KLM logo]()
$780
This KLM deal was found by Cheapflights users on 7/23. 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.
Mon 8/1010:54 am
MDW
- VCE
1 stop15h 01m
KLM
Thu 8/2011:05 am
VCE
- MDW
1 stop18h 31m
KLM
Deal found 7/23![KLM logo]()
$731
This Delta deal was found by Cheapflights users on 7/21. 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 8/111:51 pm
MDW
- VCE
2 stops14h 29m
Delta
Thu 8/2011:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/21![Delta logo]()
$735
This Delta deal was found by Cheapflights users on 7/22. 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 8/121:25 pm
MDW
- FCO
1 stop14h 35m
Delta
Wed 8/196:30 am
FCO
- MDW
2 stops18h 31m
Delta
Deal found 7/22![Delta logo]()
$731
This Air France deal was found by Cheapflights users on 7/22. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:54 am
MDW
- FCO
1 stop13h 41m
Air France
Wed 8/191:10 pm
FCO
- MDW
1 stop16h 26m
Air France
Deal found 7/22![Air France logo]()
$732
This Delta deal was found by Cheapflights users on 7/23. 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 8/121:25 pm
MDW
- VCE
2 stops14h 55m
Delta
Tue 8/2511:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/23![Delta logo]()
$771
This Delta deal was found by Cheapflights users on 7/22. 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 8/1310:54 am
MDW
- FCO
1 stop13h 41m
Delta
Thu 8/206:30 am
FCO
- MDW
2 stops18h 31m
Delta
Deal found 7/22![Delta logo]()
$781
This Delta deal was found by Cheapflights users on 7/25. 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 8/1712:46 pm
MDW
- VCE
1 stop13h 09m
Delta
Thu 8/2711:05 am
VCE
- MDW
1 stop18h 31m
Delta
Deal found 7/25![Delta logo]()
$762
One-way flights from Midway to ItalySearch for one-way flight options from Midway to Italy. Find affordable one-way fares based on user searches. Data last updated July 26, 2026.
Search for one-way flight options from Midway to Italy. Find affordable one-way fares based on user searches. Data last updated July 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 10/216:40 am
MDW
- FLR
3 stops33h 30m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 7/21. 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 10/271:00 pm
MDW
- FCO
2 stops16h 00m
Delta
Deal found 7/21![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/1711:06 am
MDW
- MXP
3 stops53h 29m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 7/22. 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 11/81:28 pm
MDW
- FCO
2 stops15h 02m
Delta
Deal found 7/22![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 7/21. 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.
Sat 11/75:21 pm
MDW
- FCO
2 stops31h 24m
Delta
Deal found 7/21![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 7/23. 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.
Sat 1/165:25 pm
MDW
- FCO
1 stop34h 55m
Delta
Deal found 7/23![Delta logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Thu 10/1512:03 pm
MDW
- FCO
3 stops54h 22m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/2911:45 am
MDW
- PMO
3 stops38h 30m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 9/3011:45 am
MDW
- PMO
3 stops48h 15m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 7/22. 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 10/201:28 pm
MDW
- FLR
2 stops15h 42m
Delta
Deal found 7/22![Delta logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 10/33:20 pm
MDW
- VCE
3 stops48h 05m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 7/21. 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 10/2112:28 pm
MDW
- FLR
2 stops15h 12m
Delta
Deal found 7/21![Delta logo]()
$369
Find flight deals from Midway to Italy
Keep the following information in mind while searching for Midway to Italy flight deals. Data was last updated July 26, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $723 (KLM) |
One-way from | $328 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $895 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Italy 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 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Italy that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Mon 11/9
10:35 am-8:15 am
1 stop14h 40m
Rome Fiumicino
Fri 11/13
6:10 am-4:50 pm
2 stops17h 40m
$732
ChicagoVenice
MDW - VCE
MDWVCE
Chicago Midway
Wed 8/12
10:54 am-8:55 am
1 stop15h 01m
Venice Marco Polo
Fri 8/21
11:05 am-10:36 pm
1 stop18h 31m
$762
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Thu 8/13
1:25 pm-11:00 am
1 stop14h 35m
Rome Fiumicino
Fri 8/21
6:30 am-6:33 pm
2 stops19h 03m
$781
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Wed 10/28
1:27 pm-9:35 am
1 stop14h 08m
Rome Fiumicino
Sat 11/7
6:10 am-6:00 pm
2 stops18h 50m
$782
ChicagoBologna
MDW - BLQ
MDWBLQ
Chicago Midway
Mon 11/9
1:00 pm-1:55 pm
2 stops17h 55m
Bologna Guglielmo Marconi
Thu 11/12
6:35 am-6:37 pm
2 stops19h 02m
$782
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Sun 8/9
10:54 am-9:25 am
1 stop15h 31m
Milan Malpensa
Fri 8/21
11:40 am-10:36 pm
1 stop17h 56m
$796
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Wed 8/26
1:25 pm-11:00 am
1 stop14h 35m
Rome Fiumicino
Tue 9/8
6:30 am-6:19 pm
2 stops18h 49m
$806
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Wed 10/14
1:28 pm-11:00 am
1 stop14h 32m
Rome Fiumicino
Thu 10/22
6:30 am-4:39 pm
2 stops17h 09m
$806
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Sat 12/5
6:30 pm-9:50 am
2 stops32h 20m
Milan Malpensa
Tue 12/8
11:00 am-6:37 pm
2 stops38h 37m
$824
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Tue 12/15
12:30 pm-10:15 am
1 stop14h 45m
Rome Fiumicino
Fri 12/25
6:10 am-4:50 pm
2 stops17h 40m
$831
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Italy
Have a flexible travel schedule? Discover the best time to fly to Italy from Midway with our price prediction graph.
MDW-FCO
MDW-VCE
MDW-MXP
MDW-FLR
MDW-BRI
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 Chicago Midway Airport to Italy
MDW-IT0
MDW-FCO
MDW-VCE
MDW-MXP
MDW-FLR
No data available for this route at this time. Please check back soon.
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