$333+ Cheap flights from Midway (MDW) to Milan (MIL)
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 — MIL
Jun 28 — Jul 51
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Milan with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to MilanExplore the most affordable flight options available from Midway to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.
Explore the most affordable flight options available from Midway to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 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 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 5/29. 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 11/2610:35 am
MDW
- MXP
1 stop17h 35m
Delta
Wed 12/166:55 am
MXP
- MDW
2 stops18h 42m
Delta
Deal found 5/29![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 5/24. 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 8/121:27 pm
MDW
- MXP
2 stops13h 58m
Delta
Sat 8/226:45 am
MXP
- MDW
2 stops15h 53m
Delta
Deal found 5/24![Delta logo]()
$857
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
- MXP
2 stops14h 13m
Delta
Sat 8/2211:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 5/24![Delta logo]()
$896
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 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 7/2612:41 pm
MDW
- MXP
1 stop13h 44m
Delta
Fri 8/1411:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 5/28![Delta logo]()
$962
Best flights from Midway to MilanDiscover carefully curated flight deals from Midway to Milan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 2026.
Discover carefully curated flight deals from Midway to Milan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 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 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.
Mon 8/248:15 am
MDW
- MXP
2 stops19h 45m
Multiple Airlines
Mon 8/316:55 am
MXP
- MDW
2 stops22h 05m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$968
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 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 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
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.
Mon 6/89:20 am
MDW
- MXP
2 stops29h 00m
Multiple Airlines
Thu 6/116:55 am
MXP
- MDW
2 stops18h 40m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,206
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 8/236:05 am
MDW
- MXP
1 stop20h 20m
KLM
Sun 8/3011:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 5/28![KLM logo]()
$1,242
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 10/189:30 am
MDW
- MXP
2 stops16h 55m
Delta
Sun 10/251:05 pm
MXP
- MDW
1 stop14h 40m
Delta
Deal found 5/27![Delta logo]()
$1,036
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:05 pm
MDW
- MXP
1 stop15h 05m
KLM
Mon 11/91:05 pm
MXP
- MDW
1 stop15h 40m
KLM
Deal found 5/25![KLM logo]()
$1,252
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.
Sat 7/181:49 pm
MDW
- MXP
2 stops13h 51m
Delta
Sat 7/2511:40 am
MXP
- MDW
1 stop17h 35m
Delta
Deal found 5/27![Delta logo]()
$1,086
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/110:55 am
MDW
- MXP
1 stop15h 30m
KLM
Sat 8/811:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 5/27![KLM logo]()
$1,320
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.
Wed 8/199:24 am
MDW
- MXP
2 stops18h 01m
Delta
Sun 8/306:45 am
MXP
- MDW
2 stops16h 30m
Delta
Deal found 5/26![Delta logo]()
$1,132
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 8/231:27 pm
MDW
- MXP
2 stops13h 58m
Delta
Sun 8/306:45 am
MXP
- MDW
2 stops18h 48m
Delta
Deal found 5/28![Delta logo]()
$1,132
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2510:55 am
MDW
- MXP
1 stop15h 30m
KLM
Sun 8/911:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 5/27![KLM logo]()
$1,467
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.
Sun 7/191:18 pm
MDW
- LIN
2 stops15h 02m
Delta
Thu 7/236:40 am
LIN
- MDW
2 stops18h 38m
Delta
Deal found 5/25![Delta logo]()
$1,211
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.
Fri 9/251:47 pm
MDW
- MXP
2 stops17h 58m
Delta
Sun 10/49:00 am
MXP
- MDW
2 stops20h 25m
Delta
Deal found 5/28![Delta logo]()
$1,470
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 8/221:51 pm
MDW
- LIN
2 stops14h 29m
Delta
Sun 8/306:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/24![Delta logo]()
$1,583
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.
Fri 8/211:27 pm
MDW
- LIN
2 stops14h 53m
Delta
Sun 8/306:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/27![Delta logo]()
$1,584
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
Fri 7/246:40 am
LIN
- MDW
2 stops18h 45m
Delta
Deal found 5/28![Delta logo]()
$1,697
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 8/81:27 pm
MDW
- LIN
2 stops14h 53m
Delta
Sun 8/166:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/24![Delta logo]()
$1,729
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.
Sun 8/2310:54 am
MDW
- LIN
2 stops14h 56m
Delta
Wed 8/266:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/25![Delta logo]()
$1,873
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.
Wed 9/1610:48 am
MDW
- LIN
2 stops15h 02m
Delta
Sat 9/266:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/26![Delta logo]()
$1,937
Last-minute flights from Midway to MilanDiscover last-minute flight deals from Midway to Milan. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Milan. Data last updated May 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/29. 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.
Tue 6/212:53 pm
MDW
- MXP
1 stop13h 32m
Delta
Fri 8/2111:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 5/29![Delta logo]()
$1,200
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.
Wed 6/37:45 am
MDW
- MXP
2 stops30h 35m
Multiple Airlines
Tue 6/97:00 am
MXP
- MDW
2 stops19h 20m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,099
This Condor deal was found by Cheapflights users on 5/29. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:45 am
MDW
- MXP
2 stops30h 35m
Multiple Airlines
Thu 8/206:55 am
MXP
- MDW
2 stops22h 05m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$1,166
This Delta deal was found by Cheapflights users on 5/29. 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.
Wed 6/31:22 pm
MDW
- MXP
2 stops14h 03m
Delta
Thu 8/2011:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 5/29![Delta logo]()
$1,204
This Delta deal was found by Cheapflights users on 5/29. 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.
Wed 6/31:22 pm
MDW
- LIN
2 stops14h 58m
Delta
Thu 8/206:40 am
LIN
- MDW
2 stops18h 53m
Delta
Deal found 5/29![Delta logo]()
$1,212
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.
Sat 6/610:15 am
MDW
- MXP
3 stops30h 10m
Multiple Airlines
Sun 6/146:30 am
MXP
- MDW
3 stops39h 05m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$1,127
This Condor 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:20 am
MDW
- MXP
2 stops29h 00m
Multiple Airlines
Thu 6/116:55 am
MXP
- MDW
2 stops18h 40m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$1,156
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 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 6/97:40 am
MDW
- MXP
2 stops20h 20m
Multiple Airlines
Fri 6/126:55 am
MXP
- MDW
2 stops18h 40m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,082
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.
Wed 6/1010:15 am
MDW
- MXP
3 stops29h 40m
Multiple Airlines
Sun 6/146:30 am
MXP
- MDW
3 stops34h 05m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$1,028
This Condor 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:25 am
MDW
- MXP
2 stops34h 35m
Multiple Airlines
Wed 6/177:00 am
MXP
- MDW
2 stops19h 20m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$1,078
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.
Sat 6/135:25 am
MDW
- MXP
2 stops34h 35m
Multiple Airlines
Thu 7/26:55 am
MXP
- MDW
2 stops18h 40m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,178
One-way flights from Midway to MilanSearch for one-way flight options from Midway to Milan. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
Search for one-way flight options from Midway to Milan. Find affordable one-way fares based on user searches. Data last updated May 29, 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 5/28. 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.
Sat 6/1310:15 am
MDW
- MXP
2 stops18h 55m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$363
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 5/25. 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 6/153:20 pm
MDW
- MXP
3 stops48h 40m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$409
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.
Sat 6/1310:15 am
MDW
- LIN
3 stops51h 00m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$416
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
- LIN
3 stops43h 15m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$432
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.
Mon 8/243:15 pm
MDW
- MXP
2 stops24h 45m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$441
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.
Thu 7/166:05 am
MDW
- MXP
3 stops34h 15m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$442
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.
Thu 7/166:05 am
MDW
- LIN
3 stops29h 35m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$461
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.
Sun 11/1512:03 pm
MDW
- LIN
3 stops40h 02m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$474
Find flight deals from Midway to Milan
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Milan (MIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 29, 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 | January |
Average price | $1,098 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Milan 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 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan 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
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
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Mon 8/24
8:15 am-11:00 am
2 stops19h 45m
Milan Malpensa
Mon 8/31
6:55 am-10:00 pm
2 stops22h 05m
$968
ChicagoMilan
MDW - LIN
MDWLIN
Chicago Midway
Sun 7/19
1:18 pm-11:20 am
2 stops15h 02m
Milan Linate
Tue 8/4
6:40 am-6:33 pm
2 stops18h 53m
$974
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Sun 10/18
9:30 am-9:25 am
2 stops16h 55m
Milan Malpensa
Sun 10/25
1:05 pm-9:45 pm
1 stop14h 40m
$1,036
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Sat 7/18
1:49 pm-10:40 am
2 stops13h 51m
Milan Malpensa
Sat 7/25
11:40 am-10:15 pm
1 stop17h 35m
$1,086
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 8/19
9:24 am-10:25 am
2 stops18h 01m
Milan Malpensa
Sun 8/30
6:45 am-4:15 pm
2 stops16h 30m
$1,132
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Sun 8/23
1:27 pm-10:25 am
2 stops13h 58m
Milan Malpensa
Sun 8/30
6:45 am-6:33 pm
2 stops18h 48m
$1,132
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 8/19
10:54 am-9:25 am
1 stop15h 31m
Milan Malpensa
Sun 8/30
11:40 am-10:36 pm
1 stop17h 56m
$1,175
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Mon 6/8
9:20 am-9:20 pm
2 stops29h 00m
Milan Malpensa
Thu 6/11
6:55 am-6:35 pm
2 stops18h 40m
$1,206
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from Midway to Milan
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Milan in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Milan flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago Midway Airport-Milan flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Milan flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Milan flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Milan flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Milan
Have a flexible travel schedule? Discover the best time to fly to Milan from Midway with our price prediction graph.
MDW-MIL
MDW-LIN
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 Milan
MDW-MIL
MDW-LIN
MDW-MXP
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Midway to Milan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Milan?
Book flights to Milan if you plan to visit one of these locationsMenaggio
Rho
Brescia
Porlezza
Assago
Stresa
Bellagio
Domodossola
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