$286+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
May 3 — May 101
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 April 3, 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 April 3, 2026.
This Trip.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/167:30 am
MDW
- FCO
1 stop24h 00m
Multiple Airlines
Sun 4/197:05 pm
FCO
- MDW
1 stop24h 55m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$641
This Trip.com deal was found by Cheapflights users on 3/31. 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.
Tue 4/147:30 am
MDW
- FCO
2 stops33h 05m
Multiple Airlines
Mon 4/207:05 am
FCO
- MDW
2 stops36h 55m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$712
This Delta deal was found by Cheapflights users on 3/31. 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 8/165:25 pm
MDW
- FCO
1 stop12h 15m
Delta
Wed 8/266:30 am
FCO
- MDW
2 stops18h 35m
Delta
Deal found 3/31![Delta logo]()
$756
This KLM deal was found by Cheapflights users on 3/31. 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 4/152:12 pm
MDW
- FCO
1 stop12h 58m
KLM
Thu 4/231:10 pm
FCO
- MDW
1 stop16h 18m
KLM
Deal found 3/31![KLM logo]()
$757
This Delta deal was found by Cheapflights users on 4/1. 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 8/121:00 pm
MDW
- FCO
2 stops15h 25m
Delta
Fri 8/216:30 am
FCO
- MDW
2 stops18h 35m
Delta
Deal found 4/1![Delta logo]()
$761
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:16 pm
MDW
- FCO
1 stop31h 54m
Delta
Tue 4/216:30 am
FCO
- MDW
2 stops19h 06m
Delta
Deal found 4/3![Delta logo]()
$762
This Delta deal was found by Cheapflights users on 3/31. 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 8/1210:35 am
MDW
- FCO
1 stop14h 00m
Delta
Wed 8/196:05 am
FCO
- MDW
2 stops17h 22m
Delta
Deal found 3/31![Delta logo]()
$764
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:30 am
MDW
- NAP
2 stops19h 00m
Delta
Fri 8/219:05 am
NAP
- MDW
1 stop19h 41m
Delta
Deal found 4/3![Delta logo]()
$768
This Delta deal was found by Cheapflights users on 4/2. 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 8/1810:35 am
MDW
- NAP
1 stop13h 30m
Delta
Tue 8/256:05 am
NAP
- MDW
2 stops19h 00m
Delta
Deal found 4/2![Delta logo]()
$775
This Delta deal was found by Cheapflights users on 4/1. 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 8/1810:35 am
MDW
- FCO
1 stop14h 00m
Delta
Mon 8/316:30 am
FCO
- MDW
2 stops18h 35m
Delta
Deal found 4/1![Delta logo]()
$806
This Delta deal was found by Cheapflights users on 3/30. 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 4/152:12 pm
MDW
- FCO
1 stop12h 58m
Delta
Mon 4/206:30 am
FCO
- MDW
2 stops18h 28m
Delta
Deal found 3/30![Delta logo]()
$807
This Delta deal was found by Cheapflights users on 3/31. 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 10/265:59 pm
MDW
- FCO
2 stops15h 16m
Delta
Mon 11/96:10 am
FCO
- MDW
2 stops19h 27m
Delta
Deal found 3/31![Delta logo]()
$810
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 April 3, 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 April 3, 2026.
This Delta deal was found by Cheapflights users on 4/1. 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 4/1512:52 pm
MDW
- FCO
1 stop14h 58m
Delta
Thu 4/236:30 am
FCO
- MDW
2 stops16h 56m
Delta
Deal found 4/1![Delta logo]()
$756
This KLM deal was found by Cheapflights users on 3/30. 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 4/152:12 pm
MDW
- FCO
1 stop12h 58m
KLM
Thu 4/239:00 am
FCO
- MDW
1 stop15h 58m
KLM
Deal found 3/30![KLM logo]()
$757
This Air France deal was found by Cheapflights users on 3/31. 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.
Sat 8/155:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Mon 8/2410:05 am
PMO
- MDW
2 stops18h 41m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$919
This KAYAK deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:45 pm
MDW
- CTA
2 stops18h 45m
Air Europa
Tue 9/229:20 pm
CTA
- MDW
2 stops26h 07m
Air Europa
Deal found 4/3![Air Europa logo]()
$1,085
This Delta deal was found by Cheapflights users on 4/1. 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 8/95:10 pm
MDW
- FCO
1 stop12h 30m
Delta
Tue 8/251:10 pm
FCO
- MDW
1 stop15h 36m
Delta
Deal found 4/1![Delta logo]()
$757
This KLM deal was found by Cheapflights users on 3/31. 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 8/1710:35 am
MDW
- VCE
1 stop15h 20m
KLM
Thu 8/2711:05 am
VCE
- MDW
1 stop17h 41m
KLM
Deal found 3/31![KLM logo]()
$810
This Delta deal was found by Cheapflights users on 4/2. 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 8/1810:35 am
MDW
- NAP
2 stops17h 55m
Delta
Tue 8/256:05 am
NAP
- MDW
2 stops19h 00m
Delta
Deal found 4/2![Delta logo]()
$779
This KLM deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:25 pm
MDW
- NAP
1 stop30h 40m
KLM
Fri 8/219:05 am
NAP
- MDW
1 stop19h 41m
KLM
Deal found 4/3![KLM logo]()
$821
This Delta deal was found by Cheapflights users on 3/31. 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 4/1610:41 am
MDW
- FCO
1 stop13h 54m
Delta
Wed 4/226:30 am
FCO
- MDW
2 stops16h 56m
Delta
Deal found 3/31![Delta logo]()
$806
This Delta deal was found by Cheapflights users on 4/1. 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 8/125:59 pm
MDW
- BLQ
2 stops16h 06m
Delta
Fri 8/216:00 am
BLQ
- MDW
2 stops19h 31m
Delta
Deal found 4/1![Delta logo]()
$812
This Mytrip deal was found by Cheapflights users on 4/1. 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 6/103:20 pm
MDW
- PMO
3 stops24h 50m
Multiple Airlines
Wed 6/2412:50 pm
PMO
- MDW
3 stops27h 50m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$1,096
This KLM deal was found by Cheapflights users on 3/31. 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 7/1311:05 am
MDW
- FCO
1 stop16h 45m
KLM
Fri 7/246:30 am
FCO
- MDW
2 stops18h 48m
KLM
Deal found 3/31![KLM logo]()
$936
This Delta deal was found by Cheapflights users on 4/2. 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 8/129:30 am
MDW
- NAP
2 stops19h 00m
Delta
Fri 8/219:05 am
NAP
- MDW
1 stop19h 41m
Delta
Deal found 4/2![Delta logo]()
$817
This Condor deal was found by Cheapflights users on 3/31. 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 5/149:25 am
MDW
- MXP
2 stops18h 35m
Multiple Airlines
Mon 5/186:55 am
MXP
- MDW
2 stops20h 50m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$1,156
This KLM deal was found by Cheapflights users on 3/31. 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 5/51:24 pm
MDW
- PSA
2 stops18h 31m
KLM
Tue 5/193:00 pm
PSA
- MDW
2 stops32h 12m
KLM
Deal found 3/31![KLM logo]()
$970
This Delta deal was found by Cheapflights users on 3/31. 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 8/121:00 pm
MDW
- FLR
2 stops16h 10m
Delta
Wed 8/196:40 am
FLR
- MDW
2 stops18h 51m
Delta
Deal found 3/31![Delta logo]()
$822
This KLM deal was found by Cheapflights users on 4/1. 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 8/166:45 pm
MDW
- BLQ
2 stops14h 50m
Multiple Airlines
Sun 8/236:15 am
BLQ
- MDW
2 stops17h 12m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$1,164
This KLM deal was found by Cheapflights users on 3/30. 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 4/2212:52 pm
MDW
- VCE
1 stop13h 03m
KLM
Thu 4/3011:05 am
VCE
- MDW
1 stop18h 23m
KLM
Deal found 3/30![KLM logo]()
$1,015
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:00 pm
MDW
- PMO
2 stops15h 15m
Delta
Mon 8/243:45 pm
PMO
- MDW
2 stops31h 42m
Delta
Deal found 4/3![Delta logo]()
$884
This Condor deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:40 am
MDW
- MXP
2 stops20h 20m
Multiple Airlines
Mon 5/256:55 am
MXP
- MDW
2 stops20h 50m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$1,224
This KLM deal was found by Cheapflights users on 3/29. 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 8/224:30 pm
MDW
- VCE
1 stop14h 00m
KLM
Thu 9/311:05 am
VCE
- MDW
1 stop17h 41m
KLM
Deal found 3/29![KLM logo]()
$1,026
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1211:05 am
MDW
- FCO
1 stop13h 30m
Delta
Tue 7/286:05 am
FCO
- MDW
2 stops19h 13m
Delta
Deal found 4/3![Delta logo]()
$944
This KLM deal was found by Cheapflights users on 4/1. 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 8/212:41 pm
MDW
- VCE
1 stop13h 14m
KLM
Sun 8/1611:05 am
VCE
- MDW
1 stop17h 41m
KLM
Deal found 4/1![KLM logo]()
$1,085
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:13 pm
MDW
- FCO
2 stops14h 12m
Delta
Tue 6/166:30 am
FCO
- MDW
2 stops19h 01m
Delta
Deal found 4/3![Delta logo]()
$946
This Condor deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:25 am
MDW
- MXP
2 stops22h 25m
Multiple Airlines
Fri 7/36:55 am
MXP
- MDW
2 stops18h 40m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$1,393
This Trip.com deal was found by Cheapflights users on 3/30. 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.
Thu 5/146:36 pm
MDW
- PSA
2 stops19h 59m
KLM
Thu 5/212:50 pm
PSA
- MDW
2 stops34h 43m
KLM
Deal found 3/30![KLM logo]()
$1,088
This Condor deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:15 am
MDW
- MXP
2 stops33h 05m
Multiple Airlines
Thu 6/256:55 am
MXP
- MDW
2 stops20h 40m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$1,489
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:27 am
MDW
- FCO
2 stops17h 43m
Delta
Thu 5/710:35 am
FCO
- MDW
2 stops14h 58m
Delta
Deal found 4/3![Delta logo]()
$1,026
This KLM deal was found by Cheapflights users on 3/30. 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 9/281:05 pm
MDW
- PMO
2 stops17h 35m
KLM
Fri 10/96:10 am
PMO
- MDW
2 stops19h 27m
KLM
Deal found 3/30![KLM logo]()
$1,135
This Delta deal was found by Cheapflights users on 3/29. 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 5/141:22 pm
MDW
- BLQ
2 stops17h 38m
Delta
Thu 5/219:20 am
BLQ
- MDW
2 stops15h 36m
Delta
Deal found 3/29![Delta logo]()
$1,028
Last-minute flights from Midway to ItalyDiscover last-minute flight deals from Midway to Italy. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Italy. Data last updated April 3, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 3/31. 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.
Tue 4/147:30 am
MDW
- FCO
2 stops33h 05m
Multiple Airlines
Mon 4/207:05 am
FCO
- MDW
2 stops36h 55m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$712
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:16 pm
MDW
- FCO
1 stop31h 54m
Delta
Tue 4/216:30 am
FCO
- MDW
2 stops19h 06m
Delta
Deal found 4/3![Delta logo]()
$762
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:16 pm
MDW
- FCO
1 stop31h 54m
Delta
Sun 4/196:30 am
FCO
- MDW
2 stops18h 28m
Delta
Deal found 4/3![Delta logo]()
$812
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:21 pm
MDW
- FCO
1 stop31h 14m
Delta
Mon 4/209:00 am
FCO
- MDW
1 stop15h 58m
Delta
Deal found 4/3![Delta logo]()
$813
This Delta deal was found by Cheapflights users on 3/31. 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 4/152:12 pm
MDW
- FCO
1 stop12h 58m
Delta
Tue 4/216:30 am
FCO
- MDW
2 stops19h 06m
Delta
Deal found 3/31![Delta logo]()
$756
This KLM deal was found by Cheapflights users on 3/31. 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 4/152:12 pm
MDW
- FCO
1 stop12h 58m
KLM
Tue 4/211:10 pm
FCO
- MDW
1 stop16h 18m
KLM
Deal found 3/31![KLM logo]()
$757
This KLM deal was found by Cheapflights users on 3/30. 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 4/152:12 pm
MDW
- FCO
1 stop12h 58m
KLM
Mon 4/209:00 am
FCO
- MDW
1 stop15h 58m
KLM
Deal found 3/30![KLM logo]()
$807
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/157:30 am
MDW
- FCO
1 stop17h 25m
Multiple Airlines
Sun 4/197:05 pm
FCO
- MDW
1 stop24h 55m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$834
This Delta deal was found by Cheapflights users on 4/1. 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 4/156:00 am
MDW
- NAP
2 stops19h 10m
Delta
Tue 4/2110:15 am
NAP
- MDW
2 stops19h 13m
Delta
Deal found 4/1![Delta logo]()
$870
This Trip.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/167:30 am
MDW
- FCO
1 stop24h 00m
Multiple Airlines
Sun 4/197:05 pm
FCO
- MDW
1 stop24h 55m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$641
This Delta deal was found by Cheapflights users on 3/31. 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 4/1610:41 am
MDW
- FCO
1 stop13h 54m
Delta
Wed 4/226:30 am
FCO
- MDW
2 stops16h 56m
Delta
Deal found 3/31![Delta logo]()
$806
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/167:30 am
MDW
- MXP
1 stop16h 30m
Multiple Airlines
Wed 4/227:20 am
MXP
- MDW
2 stops31h 06m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$889
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 April 3, 2026.
Search for one-way flight options from Midway to Italy. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/217:30 am
MDW
- MXP
2 stops24h 40m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/217:30 am
MDW
- LIN
2 stops28h 10m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 6/410:25 am
MDW
- MXP
3 stops48h 50m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 6/83:20 pm
MDW
- FCO
3 stops50h 05m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/1910:30 am
MDW
- MXP
3 stops29h 30m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 4/187:30 am
MDW
- FCO
2 stops27h 50m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 6/1610:25 am
MDW
- FCO
3 stops25h 55m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 6/13:20 pm
MDW
- VCE
3 stops45h 30m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/232:15 pm
MDW
- MXP
3 stops41h 10m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$405
This KLM deal was found by Cheapflights users on 4/1. 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 8/305:25 pm
MDW
- CTA
2 stops15h 20m
KLM
Deal found 4/1![KLM logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/157:30 am
MDW
- FCO
3 stops55h 10m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 6/53:20 pm
MDW
- FCO
2 stops37h 10m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$411
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 April 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $630 (Kiwi.com) |
One-way from | $286 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $762 |
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 April 3, 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
Wed 4/15
12:52 pm-10:50 am
1 stop14h 58m
Rome Fiumicino
Thu 4/23
6:30 am-4:26 pm
2 stops16h 56m
$756
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Wed 4/15
2:12 pm-10:10 am
1 stop12h 58m
Rome Fiumicino
Thu 4/23
9:00 am-5:58 pm
1 stop15h 58m
$757
Quickest round-trip
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Sun 8/9
5:10 pm-12:40 pm
1 stop12h 30m
Rome Fiumicino
Tue 8/25
1:10 pm-9:46 pm
1 stop15h 36m
$757
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Tue 8/18
10:35 am-11:30 am
2 stops17h 55m
Naples
Tue 8/25
6:05 am-6:05 pm
2 stops19h 00m
$779
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Thu 4/16
10:41 am-7:35 am
1 stop13h 54m
Rome Fiumicino
Wed 4/22
6:30 am-4:26 pm
2 stops16h 56m
$806
ChicagoVenice
MDW - VCE
MDWVCE
Chicago Midway
Mon 8/17
10:35 am-8:55 am
1 stop15h 20m
Venice Marco Polo
Thu 8/27
11:05 am-9:46 pm
1 stop17h 41m
$810
ChicagoBologna
MDW - BLQ
MDWBLQ
Chicago Midway
Wed 8/12
5:59 pm-5:05 pm
2 stops16h 06m
Bologna Guglielmo Marconi
Fri 8/21
6:00 am-6:31 pm
2 stops19h 31m
$812
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Wed 8/12
9:30 am-11:30 am
2 stops19h 00m
Naples
Fri 8/21
9:05 am-9:46 pm
1 stop19h 41m
$817
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Wed 8/12
5:25 pm-7:05 am
1 stop30h 40m
Naples
Fri 8/21
9:05 am-9:46 pm
1 stop19h 41m
$821
ChicagoFlorence
MDW - FLR
MDWFLR
Chicago Midway
Wed 8/12
1:00 pm-12:10 pm
2 stops16h 10m
Florence Peretola
Wed 8/19
6:40 am-6:31 pm
2 stops18h 51m
$822
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-MXP
MDW-LIN
MDW-CTA
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-MXP
MDW-LIN
No data available for this route at this time. Please check back soon.
Related info for your journey
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