$282+ Cheap flights from Midway (MDW) to Italy
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Oct 13 — Oct 201
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 September 13, 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 September 13, 2026.
This KLM deal was found by Cheapflights users on 9/12. 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 -
1 stop12h 10m
Wed 11/1810:00 am -
1 stop15h 04m
Deal found 9/12![KLM logo]()
$577
This Delta deal was found by Cheapflights users on 9/12. 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 11/91:05 pm -
1 stop12h 10m
Wed 11/1810:00 am -
2 stops19h 54m
Deal found 9/12![Delta logo]()
$582
This Delta deal was found by Cheapflights users on 9/9. 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 10/1812:49 pm -
1 stop13h 06m
Thu 11/512:10 pm -
2 stops17h 23m
Deal found 9/9![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 9/9. 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 10/2612:49 pm -
2 stops17h 26m
Wed 11/116:30 am -
2 stops17h 09m
Deal found 9/9![Delta logo]()
$607
This Air France deal was found by Cheapflights users on 9/10. 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 10/266:44 pm -
2 stops14h 16m
Wed 11/116:30 am -
2 stops16h 48m
Deal found 9/10![Multiple Airlines logo]()
$614
This Delta deal was found by Cheapflights users on 9/9. 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 10/1812:49 pm -
1 stop13h 06m
Tue 11/36:05 am -
2 stops17h 42m
Deal found 9/9![Delta logo]()
$656
This Delta deal was found by Cheapflights users on 9/9. 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 12/71:41 pm -
2 stops14h 29m
Mon 12/146:05 am -
2 stops17h 45m
Deal found 9/9![Delta logo]()
$672
This Delta deal was found by Cheapflights users on 9/11. 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 10/2110:59 am -
1 stop13h 36m
Wed 11/41:30 pm -
1 stop16h 03m
Deal found 9/11![Delta logo]()
$676
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:29 am -
1 stop18h 06m
Sat 11/710:00 am -
1 stop15h 00m
Deal found 9/8![Delta logo]()
$677
This KLM deal was found by Cheapflights users on 9/11. 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 11/281:05 pm -
1 stop12h 10m
Mon 12/710:00 am -
1 stop15h 01m
Deal found 9/11![KLM logo]()
$678
This Delta deal was found by Cheapflights users on 9/12. 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 12/299:30 am -
2 stops16h 40m
Sun 1/106:00 am -
2 stops17h 50m
Deal found 9/12![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 9/11. 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 10/2812:49 pm -
2 stops14h 46m
Wed 11/411:45 am -
2 stops17h 48m
Deal found 9/11![Delta logo]()
$681
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 September 13, 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 September 13, 2026.
This Delta deal was found by Cheapflights users on 9/12. 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 11/91:05 pm -
1 stop12h 10m
Wed 11/1810:00 am -
2 stops19h 54m
Deal found 9/12![Delta logo]()
$582
This KLM deal was found by Cheapflights users on 9/10. 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 2/181:00 pm -
2 stops13h 45m
Thu 2/2511:20 am -
2 stops17h 50m
Deal found 9/10![KLM logo]()
$671
This Air France deal was found by Cheapflights users on 9/10. 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 10/256:44 pm -
2 stops18h 06m
Sun 11/16:30 am -
2 stops18h 30m
Deal found 9/10![Air France logo]()
$1,044
This Delta deal was found by Cheapflights users on 9/9. 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 10/186:04 am -
1 stop19h 51m
Fri 11/612:10 pm -
2 stops17h 23m
Deal found 9/9![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 9/9. 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 10/1912:49 pm -
1 stop13h 06m
Thu 11/512:10 pm -
2 stops17h 23m
Deal found 9/9![Delta logo]()
$603
This KLM deal was found by Cheapflights users on 9/13. 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 11/191:31 pm -
2 stops15h 14m
Tue 12/112:55 pm -
1 stop17h 00m
Deal found 9/13![Multiple Airlines logo]()
$1,433
This Delta deal was found by Cheapflights users on 9/11. 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 10/266:44 pm -
2 stops14h 16m
Wed 11/1112:10 pm -
2 stops17h 44m
Deal found 9/11![Delta logo]()
$612
This Delta deal was found by Cheapflights users on 9/9. 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 10/1812:49 pm -
1 stop13h 06m
Tue 11/36:05 am -
2 stops17h 42m
Deal found 9/9![Delta logo]()
$656
This KLM deal was found by Cheapflights users on 9/13. 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 12/91:02 pm -
2 stops14h 38m
Wed 3/36:40 am -
2 stops16h 45m
Deal found 9/13![KLM logo]()
$879
This Delta deal was found by Cheapflights users on 9/10. 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 11/2711:27 am -
1 stop13h 48m
Sun 12/61:30 pm -
1 stop16h 25m
Deal found 9/10![Delta logo]()
$677
This Delta deal was found by Cheapflights users on 9/10. 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 2/1810:35 am -
2 stops15h 20m
Thu 2/256:30 am -
2 stops19h 07m
Deal found 9/10![Delta logo]()
$677
This KLM deal was found by Cheapflights users on 9/11. 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 10/191:27 pm -
2 stops18h 08m
Wed 11/411:20 am -
2 stops18h 13m
Deal found 9/11![KLM logo]()
$992
This Delta deal was found by Cheapflights users on 9/10. 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 10/119:29 am -
2 stops18h 51m
Mon 12/712:10 pm -
2 stops17h 45m
Deal found 9/10![Delta logo]()
$710
This KLM deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:59 am -
2 stops17h 31m
Thu 10/296:10 am -
2 stops17h 50m
Deal found 9/8![KLM logo]()
$1,055
This Delta deal was found by Cheapflights users on 9/12. 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 11/141:31 pm -
2 stops18h 29m
Sat 11/216:05 am -
2 stops17h 34m
Deal found 9/12![Delta logo]()
$722
This KLM deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:59 am -
1 stop15h 26m
Wed 10/1411:40 am -
1 stop17h 53m
Deal found 9/8![KLM logo]()
$1,124
This Delta deal was found by Cheapflights users on 9/11. 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 11/312:27 pm -
2 stops15h 43m
Sat 11/146:05 am -
2 stops18h 59m
Deal found 9/11![Delta logo]()
$725
This Delta deal was found by Cheapflights users on 9/11. 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 1/225:25 pm -
2 stops16h 45m
Sun 1/316:05 am -
2 stops17h 20m
Deal found 9/11![Delta logo]()
$727
This Air France deal was found by Cheapflights users on 9/12. 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 12/289:58 am -
2 stops16h 47m
Fri 1/86:30 am -
2 stops22h 40m
Deal found 9/12![Multiple Airlines logo]()
$1,771
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:04 am -
1 stop18h 31m
Wed 10/219:00 am -
1 stop16h 00m
Deal found 9/8![Delta logo]()
$775
This KLM deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:31 pm -
2 stops14h 34m
Sat 10/2412:20 pm -
2 stops17h 13m
Deal found 9/8![KLM logo]()
$1,386
This Air France deal was found by Cheapflights users on 9/9. 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 10/45:10 pm -
2 stops16h 25m
Tue 10/206:30 am -
2 stops18h 30m
Deal found 9/9![Multiple Airlines logo]()
$1,940
This Delta deal was found by Cheapflights users on 9/11. 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 11/229:30 am -
2 stops18h 15m
Tue 12/110:00 am -
1 stop15h 01m
Deal found 9/11![Delta logo]()
$780
This KLM deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:31 pm -
2 stops17h 59m
Fri 12/46:30 am -
2 stops18h 31m
Deal found 9/8![KLM logo]()
$1,432
This Delta deal was found by Cheapflights users on 9/9. 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 10/279:29 am -
2 stops17h 21m
Fri 1/1512:00 pm -
2 stops27h 45m
Deal found 9/9![Delta logo]()
$786
This Delta deal was found by Cheapflights users on 9/10. 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 2/85:25 pm -
2 stops14h 30m
Wed 2/1712:55 pm -
1 stop16h 15m
Deal found 9/10![Delta logo]()
$791
This KLM deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:31 pm -
2 stops14h 34m
Mon 10/266:10 am -
2 stops17h 50m
Deal found 9/8![KLM logo]()
$1,588
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:44 pm -
2 stops13h 11m
Tue 11/106:30 am -
2 stops18h 34m
Deal found 9/8![Delta logo]()
$793
This Delta deal was found by Cheapflights users on 9/9. 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 10/2612:49 pm -
2 stops15h 11m
Mon 1/111:00 pm -
2 stops40h 10m
Deal found 9/9![Delta logo]()
$798
This KLM deal was found by Cheapflights users on 9/9. 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 10/710:59 am -
2 stops17h 31m
Fri 10/166:10 am -
2 stops18h 50m
Deal found 9/9![KLM logo]()
$1,713
Last-minute flights from Midway to ItalyDiscover last-minute flight deals from Midway to Italy. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Italy. Data last updated September 13, 2026 and is based on user searches.
This Condor deal was found by Cheapflights users on 9/10. 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 9/156:40 am -
2 stops32h 10m
Fri 9/188:10 am -
2 stops20h 50m
Deal found 9/10![Multiple Airlines logo]()
$707
This Delta deal was found by Cheapflights users on 9/11. 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 10/119:29 am -
2 stops18h 51m
Mon 12/712:10 pm -
2 stops17h 45m
Deal found 9/11![Delta logo]()
$710
This Air France deal was found by Cheapflights users on 9/11. 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 10/175:31 pm -
1 stop12h 09m
Sat 11/141:30 pm -
1 stop16h 24m
Deal found 9/11![Multiple Airlines logo]()
$678
This Delta deal was found by Cheapflights users on 9/9. 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 10/1812:49 pm -
1 stop13h 06m
Thu 11/512:10 pm -
2 stops17h 23m
Deal found 9/9![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 9/9. 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 10/1812:49 pm -
1 stop13h 06m
Tue 11/36:05 am -
2 stops17h 42m
Deal found 9/9![Delta logo]()
$656
This Delta deal was found by Cheapflights users on 9/11. 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 10/2110:59 am -
1 stop13h 36m
Wed 11/41:30 pm -
1 stop16h 03m
Deal found 9/11![Delta logo]()
$676
This Delta deal was found by Cheapflights users on 9/9. 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 10/2612:49 pm -
2 stops17h 26m
Wed 11/116:30 am -
2 stops17h 09m
Deal found 9/9![Delta logo]()
$607
This Air France deal was found by Cheapflights users on 9/10. 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 10/266:44 pm -
2 stops14h 16m
Wed 11/116:30 am -
2 stops16h 48m
Deal found 9/10![Multiple Airlines logo]()
$614
This Delta deal was found by Cheapflights users on 9/12. 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 10/271:27 pm -
1 stop14h 08m
Tue 11/36:00 am -
2 stops17h 47m
Deal found 9/12![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 9/11. 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 10/2812:49 pm -
2 stops15h 56m
Wed 11/410:00 am -
1 stop15h 00m
Deal found 9/11![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:49 pm -
2 stops14h 46m
Sat 11/71:30 pm -
1 stop16h 03m
Deal found 9/10![Delta logo]()
$682
This KLM deal was found by Cheapflights users on 9/9. 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 10/301:27 pm -
1 stop14h 08m
Sat 11/1410:00 am -
1 stop15h 04m
Deal found 9/9![KLM logo]()
$677
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 September 13, 2026.
Search for one-way flight options from Midway to Italy. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/133:20 pm -
2 stops24h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/13:20 pm -
3 stops51h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/83:20 pm -
3 stops51h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 -
3 stops41h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/103:20 pm -
2 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/113:20 pm -
2 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/1411:45 am -
3 stops43h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:20 pm -
3 stops35h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/133:20 pm -
3 stops23h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:20 pm -
3 stops49h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/146:21 am -
3 stops50h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2711:45 am -
2 stops27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$335
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 September 13, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $577 (KLM) |
One-way from | $282 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $937 |
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 7,457,451 searches. Data last updated September 13, 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
ChicagoNaples
MDW Chicago Midway - NAP Naples
MDWNAP
Chicago Midway
Sat 10/3
3:20 pm-4:00 pm
3 stops41h 40m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$313
ChicagoMilan
MDW Chicago Midway - LIN Milan Linate
MDWLIN
Chicago Midway
Sat 9/26
3:20 pm-10:40 am
2 stops36h 20m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$362
ChicagoBologna
MDW Chicago Midway - BLQ Bologna Guglielmo Marconi
MDWBLQ
Chicago Midway
Sun 2/28
9:55 am-10:15 am
2 stops17h 20m
Bologna Guglielmo Marconi
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$365
ChicagoBologna
MDW Chicago Midway - BLQ Bologna Guglielmo Marconi
MDWBLQ
Chicago Midway
Mon 3/1
1:00 pm-1:55 pm
2 stops17h 55m
Bologna Guglielmo Marconi
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$365
ChicagoBari
MDW Chicago Midway - BRI Bari Palese
MDWBRI
Chicago Midway
Wed 10/7
3:20 pm-7:15 am
3 stops56h 55m
Bari Palese
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$369
ChicagoVenice
MDW Chicago Midway - VCE Venice Marco Polo
MDWVCE
Chicago Midway
Sun 9/27
11:45 am-10:25 pm
2 stops27h 40m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$408
ChicagoFlorence
MDW Chicago Midway - FLR Florence Peretola
MDWFLR
Chicago Midway
Fri 12/11
12:39 pm-11:35 am
2 stops15h 56m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$415
ChicagoVenice
MDW Chicago Midway - VCE Venice Marco Polo
MDWVCE
Chicago Midway
Fri 10/2
9:24 pm-2:50 pm
3 stops58h 26m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$419
ChicagoBari
MDW Chicago Midway - BRI Bari Palese
MDWBRI
Chicago Midway
Sun 11/15
6:42 pm-8:20 am
3 stops54h 38m
Bari Palese
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$441
ChicagoNaples
MDW Chicago Midway - NAP Naples
MDWNAP
Chicago Midway
Mon 10/26
1:26 pm-9:15 pm
3 stops49h 49m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$449
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-BRI
MDW-VCE
MDW-MXP
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-BRI
MDW-VCE
No data available for this route at this time. Please check back soon.
Related info for your journey
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