$333+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Jun 27 — Jul 41
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Italy with Cheapflights
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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 May 28, 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 May 28, 2026.
This Delta deal was found by Cheapflights users on 5/25. 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 8/129:24 am
MDW
- MXP
2 stops25h 11m
Delta
Wed 8/1911:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 5/25![Delta logo]()
$796
This Delta deal was found by Cheapflights users on 5/28. 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 7/254:22 pm
MDW
- MXP
1 stop34h 03m
Delta
Thu 8/2011:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 5/28![Delta logo]()
$797
This Delta deal was found by Cheapflights users on 5/24. 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
- LIN
2 stops14h 56m
Delta
Fri 8/216:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/24![Delta logo]()
$803
This Delta deal was found by Cheapflights users on 5/28. 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 8/1610:54 am
MDW
- FLR
2 stops15h 01m
Delta
Tue 8/256:30 am
FLR
- MDW
2 stops18h 31m
Delta
Deal found 5/28![Delta logo]()
$816
This Delta deal was found by Cheapflights users on 5/26. 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.
Mon 8/101:27 pm
MDW
- PMO
2 stops18h 33m
Delta
Thu 8/203:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 5/26![Delta logo]()
$835
This KLM deal was found by Cheapflights users on 5/28. 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 8/1610:54 am
MDW
- MXP
1 stop15h 31m
KLM
Mon 8/3111:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 5/28![KLM logo]()
$842
This Delta deal was found by Cheapflights users on 5/28. 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 8/1612:46 pm
MDW
- MXP
2 stops14h 39m
Delta
Mon 8/3111:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 5/28![Delta logo]()
$846
This KLM deal was found by Cheapflights users on 5/28. 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 8/154:39 pm
MDW
- MXP
1 stop33h 46m
KLM
Sun 8/3011:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 5/28![KLM logo]()
$848
This Delta deal was found by Cheapflights users on 5/28. 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 7/221:49 pm
MDW
- FCO
2 stops14h 36m
Delta
Wed 7/299:00 am
FCO
- MDW
1 stop16h 25m
Delta
Deal found 5/28![Delta logo]()
$852
This Delta deal was found by Cheapflights users on 5/28. 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 11/261:05 pm
MDW
- MXP
1 stop15h 05m
Delta
Wed 12/166:55 am
MXP
- MDW
2 stops18h 42m
Delta
Deal found 5/28![Delta logo]()
$853
This Delta deal was found by Cheapflights users on 5/27. 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 11/2610:35 am
MDW
- LIN
2 stops15h 10m
Delta
Wed 12/166:30 am
LIN
- MDW
2 stops17h 20m
Delta
Deal found 5/27![Delta logo]()
$853
This Delta deal was found by Cheapflights users on 5/27. 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 7/191:18 pm
MDW
- FCO
2 stops15h 27m
Delta
Tue 7/286:30 am
FCO
- MDW
2 stops18h 55m
Delta
Deal found 5/27![Delta logo]()
$856
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 May 28, 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 May 28, 2026.
This Delta deal was found by Cheapflights users on 5/24. 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
- LIN
2 stops14h 56m
Delta
Fri 8/216:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/24![Delta logo]()
$803
This Air France deal was found by Cheapflights users on 5/25. 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.
Mon 8/105:10 pm
MDW
- BRI
2 stops16h 25m
Air France
Sun 8/3010:35 am
BRI
- MDW
2 stops19h 01m
Air France
Deal found 5/25![Air France logo]()
$984
This Condor deal was found by Cheapflights users on 5/28. 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.
Thu 8/138:15 am
MDW
- VCE
2 stops29h 30m
Multiple Airlines
Tue 8/258:20 am
VCE
- MDW
2 stops19h 30m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,040
This KLM deal was found by Cheapflights users on 5/24. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1911:05 am
MDW
- FCO
1 stop13h 30m
KLM
Sat 6/272:45 pm
FCO
- MDW
1 stop14h 32m
KLM
Deal found 5/24![KLM logo]()
$1,077
This Delta deal was found by Cheapflights users on 5/25. 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.
Sat 8/159:59 am
MDW
- PMO
2 stops19h 16m
Delta
Mon 8/243:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 5/25![Delta logo]()
$885
This Delta deal was found by Cheapflights users on 5/28. 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 7/2911:05 am
MDW
- FLR
2 stops14h 55m
Delta
Tue 8/116:30 am
FLR
- MDW
2 stops18h 31m
Delta
Deal found 5/28![Delta logo]()
$902
This Delta deal was found by Cheapflights users on 5/24. 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.
Sat 8/151:27 pm
MDW
- LIN
2 stops14h 53m
Delta
Sat 8/226:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/24![Delta logo]()
$903
This KLM deal was found by Cheapflights users on 5/26. 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 10/141:05 pm
MDW
- VCE
1 stop12h 50m
KLM
Wed 10/2111:05 am
VCE
- MDW
1 stop17h 40m
KLM
Deal found 5/26![KLM logo]()
$1,094
This Condor deal was found by Cheapflights users on 5/26. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
MDW
- FCO
2 stops32h 45m
Multiple Airlines
Mon 8/248:10 am
FCO
- MDW
2 stops20h 50m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,170
This KLM deal was found by Cheapflights users on 5/24. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:56 am
MDW
- MXP
1 stop15h 29m
KLM
Sat 8/2211:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 5/24![KLM logo]()
$1,097
This Delta deal was found by Cheapflights users on 5/26. 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.
Sun 7/196:58 pm
MDW
- BLQ
2 stops14h 37m
Delta
Tue 8/46:15 am
BLQ
- MDW
2 stops19h 18m
Delta
Deal found 5/26![Delta logo]()
$910
This Mytrip deal was found by Cheapflights users on 5/28. 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.
Thu 6/1110:15 am
MDW
- BRI
3 stops24h 00m
Multiple Airlines
Wed 6/171:00 pm
BRI
- MDW
3 stops27h 40m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,204
This KLM deal was found by Cheapflights users on 5/24. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:18 pm
MDW
- FCO
1 stop14h 42m
KLM
Mon 7/209:00 am
FCO
- MDW
1 stop16h 25m
KLM
Deal found 5/24![KLM logo]()
$1,117
This Delta deal was found by Cheapflights users on 5/28. 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 6/289:17 am
MDW
- FCO
1 stop18h 43m
Delta
Tue 7/286:30 am
FCO
- MDW
2 stops18h 55m
Delta
Deal found 5/28![Delta logo]()
$937
This Delta deal was found by Cheapflights users on 5/25. 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 6/246:00 am
MDW
- FCO
1 stop18h 35m
Delta
Fri 7/319:00 am
FCO
- MDW
1 stop16h 25m
Delta
Deal found 5/25![Delta logo]()
$937
This KLM deal was found by Cheapflights users on 5/26. 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.
Sun 9/135:25 pm
MDW
- CTA
2 stops15h 20m
KLM
Mon 10/510:15 am
CTA
- MDW
2 stops19h 10m
KLM
Deal found 5/26![KLM logo]()
$1,163
This Delta deal was found by Cheapflights users on 5/24. 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.
Sun 6/281:26 pm
MDW
- FCO
1 stop14h 34m
Delta
Tue 7/149:00 am
FCO
- MDW
1 stop16h 25m
Delta
Deal found 5/24![Delta logo]()
$937
This KLM deal was found by Cheapflights users on 5/24. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:14 pm
MDW
- PMO
2 stops17h 26m
KLM
Mon 10/126:10 am
PMO
- MDW
2 stops19h 27m
KLM
Deal found 5/24![KLM logo]()
$1,165
This Air France deal was found by Cheapflights users on 5/26. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:05 am
MDW
- BRI
2 stops15h 25m
Multiple Airlines
Thu 7/306:30 am
BRI
- MDW
2 stops18h 55m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,412
This Delta deal was found by Cheapflights users on 5/28. 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 6/91:26 pm
MDW
- FCO
2 stops14h 59m
Delta
Tue 6/306:30 am
FCO
- MDW
2 stops18h 48m
Delta
Deal found 5/28![Delta logo]()
$941
This KLM deal was found by Cheapflights users on 5/26. 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 8/1910:54 am
MDW
- MXP
1 stop15h 31m
KLM
Sun 8/3011:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 5/26![KLM logo]()
$1,175
This Condor deal was found by Cheapflights users on 5/26. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:40 am
MDW
- MXP
2 stops20h 20m
Multiple Airlines
Thu 8/66:55 am
MXP
- MDW
2 stops22h 05m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,530
This Delta deal was found by Cheapflights users on 5/25. 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.
Thu 8/61:27 pm
MDW
- FLR
2 stops15h 03m
Delta
Tue 8/116:30 am
FLR
- MDW
2 stops18h 31m
Delta
Deal found 5/25![Delta logo]()
$951
This KLM deal was found by Cheapflights users on 5/24. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:10 pm
MDW
- FCO
1 stop12h 30m
KLM
Sun 10/189:00 am
FCO
- MDW
1 stop16h 37m
KLM
Deal found 5/24![KLM logo]()
$1,216
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 8/131:51 pm
MDW
- FLR
2 stops15h 19m
Delta
Tue 8/186:30 am
FLR
- MDW
2 stops18h 31m
Delta
Deal found 5/24![Delta logo]()
$951
This KLM deal was found by Cheapflights users on 5/26. 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.
Sun 10/1110:35 am
MDW
- FCO
1 stop14h 00m
KLM
Sat 10/241:10 pm
FCO
- MDW
1 stop15h 35m
KLM
Deal found 5/26![KLM logo]()
$1,216
This Air France deal was found by Cheapflights users on 5/28. 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.
Fri 7/31:26 pm
MDW
- CTA
2 stops15h 14m
Multiple Airlines
Fri 7/316:00 am
CTA
- MDW
2 stops19h 25m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,641
This Delta deal was found by Cheapflights users on 5/28. 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 7/301:18 pm
MDW
- FLR
2 stops15h 12m
Delta
Tue 8/116:30 am
FLR
- MDW
2 stops19h 03m
Delta
Deal found 5/28![Delta logo]()
$952
This KLM deal was found by Cheapflights users on 5/28. 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 10/125:25 pm
MDW
- NAP
1 stop30h 40m
KLM
Mon 10/199:05 am
NAP
- MDW
1 stop19h 40m
KLM
Deal found 5/28![KLM logo]()
$1,229
This Delta deal was found by Cheapflights users on 5/28. 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 7/191:18 pm
MDW
- LIN
2 stops15h 02m
Delta
Tue 8/46:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/28![Delta logo]()
$974
Last-minute flights from Midway to ItalyDiscover last-minute flight deals from Midway to Italy. Data last updated May 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Italy. Data last updated May 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/24. 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.
Fri 6/510:15 am
MDW
- FCO
2 stops30h 05m
Multiple Airlines
Sun 6/72:15 pm
FCO
- MDW
1 stop26h 20m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$888
This Mytrip deal was found by Cheapflights users on 5/25. 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 6/910:15 am
MDW
- FCO
2 stops16h 00m
Multiple Airlines
Mon 6/152:20 pm
FCO
- MDW
3 stops26h 15m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$876
This Mytrip deal was found by Cheapflights users on 5/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:15 am
MDW
- NAP
3 stops29h 25m
Multiple Airlines
Sat 6/1311:25 am
NAP
- MDW
2 stops29h 10m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,008
This Condor deal was found by Cheapflights users on 5/26. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:00 am
MDW
- MXP
2 stops31h 00m
Multiple Airlines
Tue 6/167:00 am
MXP
- MDW
2 stops19h 20m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,024
This Mytrip deal was found by Cheapflights users on 5/27. 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.
Wed 6/1010:15 am
MDW
- FCO
2 stops17h 10m
Multiple Airlines
Wed 6/1712:15 pm
FCO
- MDW
2 stops28h 25m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$872
This Mytrip deal was found by Cheapflights users on 5/27. 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.
Wed 6/1010:15 am
MDW
- FCO
2 stops17h 10m
Multiple Airlines
Tue 6/1612:15 pm
FCO
- MDW
2 stops28h 20m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$875
This Mytrip deal was found by Cheapflights users on 5/27. 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.
Wed 6/1010:15 am
MDW
- FCO
2 stops17h 10m
Porter Airlines
Wed 6/1712:15 pm
FCO
- MDW
2 stops28h 25m
Porter Airlines
Deal found 5/27![Porter Airlines logo]()
$882
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 6/1210:15 am
MDW
- FCO
2 stops30h 05m
Multiple Airlines
Sun 6/142:15 pm
FCO
- MDW
1 stop26h 20m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$866
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 6/1210:15 am
MDW
- VCE
1 stop18h 15m
Multiple Airlines
Tue 6/231:25 pm
VCE
- MDW
1 stop27h 15m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,008
This Mytrip deal was found by Cheapflights users on 5/28. 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.
Sat 6/1310:15 am
MDW
- FCO
2 stops18h 30m
Multiple Airlines
Wed 6/172:20 pm
FCO
- MDW
2 stops26h 20m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$873
This Mytrip deal was found by Cheapflights users on 5/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2310:25 am
MDW
- FCO
2 stops17h 00m
Multiple Airlines
Tue 6/3012:15 pm
FCO
- MDW
2 stops28h 25m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$886
This Mytrip deal was found by Cheapflights users on 5/27. 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.
Wed 6/2410:25 am
MDW
- FCO
2 stops17h 00m
Multiple Airlines
Fri 7/312:15 pm
FCO
- MDW
2 stops28h 25m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$887
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 May 28, 2026.
Search for one-way flight options from Midway to Italy. Find affordable one-way fares based on user searches. Data last updated May 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/24. 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.
Mon 7/1310:20 am
MDW
- MXP
3 stops47h 50m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 7/103:20 pm
MDW
- MXP
3 stops36h 00m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:15 am
MDW
- MXP
3 stops31h 00m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1310:15 am
MDW
- BLQ
3 stops52h 20m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 8/2710:20 am
MDW
- BLQ
3 stops51h 35m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/126:05 am
MDW
- MXP
3 stops46h 05m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2310:25 am
MDW
- NAP
3 stops27h 45m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 7/110:20 am
MDW
- MXP
3 stops50h 40m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 5/24. 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.
Sun 7/510:20 am
MDW
- FLR
3 stops53h 35m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 5/28. 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 8/196:05 am
MDW
- CTA
2 stops18h 50m
Delta
Deal found 5/28![Delta logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 6/123:20 pm
MDW
- VCE
3 stops46h 30m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 5/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:03 pm
MDW
- VCE
3 stops43h 32m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$388
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 May 28, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $796 (Delta) |
One-way from | $333 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $871 |
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 May 28, 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
ChicagoMilan
MDW - LIN
MDWLIN
Chicago Midway
Wed 8/12
10:54 am-8:50 am
2 stops14h 56m
Milan Linate
Fri 8/21
6:40 am-6:33 pm
2 stops18h 53m
$803
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Sat 8/15
9:59 am-12:15 pm
2 stops19h 16m
Palermo Punta Raisi
Mon 8/24
3:45 pm-4:15 pm
2 stops31h 30m
$885
ChicagoFlorence
MDW - FLR
MDWFLR
Chicago Midway
Wed 7/29
11:05 am-9:00 am
2 stops14h 55m
Florence Peretola
Tue 8/11
6:30 am-6:01 pm
2 stops18h 31m
$902
ChicagoMilan
MDW - LIN
MDWLIN
Chicago Midway
Sat 8/15
1:27 pm-11:20 am
2 stops14h 53m
Milan Linate
Sat 8/22
6:40 am-6:33 pm
2 stops18h 53m
$903
ChicagoBologna
MDW - BLQ
MDWBLQ
Chicago Midway
Sun 7/19
6:58 pm-4:35 pm
2 stops14h 37m
Bologna Guglielmo Marconi
Tue 8/4
6:15 am-6:33 pm
2 stops19h 18m
$910
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Sun 6/28
9:17 am-11:00 am
1 stop18h 43m
Rome Fiumicino
Tue 7/28
6:30 am-6:25 pm
2 stops18h 55m
$937
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Wed 6/24
6:00 am-7:35 am
1 stop18h 35m
Rome Fiumicino
Fri 7/31
9:00 am-6:25 pm
1 stop16h 25m
$937
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Sun 6/28
1:26 pm-11:00 am
1 stop14h 34m
Rome Fiumicino
Tue 7/14
9:00 am-6:25 pm
1 stop16h 25m
$937
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Tue 6/9
1:26 pm-11:25 am
2 stops14h 59m
Rome Fiumicino
Tue 6/30
6:30 am-6:18 pm
2 stops18h 48m
$941
ChicagoFlorence
MDW - FLR
MDWFLR
Chicago Midway
Thu 8/6
1:27 pm-11:30 am
2 stops15h 03m
Florence Peretola
Tue 8/11
6:30 am-6:01 pm
2 stops18h 31m
$951
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-NAP
MDW-VCE
MDW-MXP
MDW-LIN
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-NAP
MDW-VCE
MDW-MXP
No data available for this route at this time. Please check back soon.
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