$299+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIL
Mar 13 — Mar 201
1 adult, Economy
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Find cheap flights from Midway to Milan with Cheapflights
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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 February 11, 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/8. 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.
Wed 8/121:00 pm
MDW
- LIN
2 stops16h 00m
Delta
Fri 8/216:25 am
LIN
- MDW
2 stops19h 06m
Delta
Deal found 2/8![Delta logo]()
$855
This KLM deal was found by Cheapflights users on 2/10. 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.
Wed 10/211:05 pm
MDW
- MXP
1 stop13h 20m
KLM
Mon 11/911:05 am
MXP
- MDW
1 stop17h 40m
KLM
Deal found 2/10![KLM logo]()
$881
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 10/211:05 pm
MDW
- MXP
2 stops16h 00m
Delta
Mon 11/911:05 am
MXP
- MDW
1 stop17h 40m
Delta
Deal found 2/10![Delta logo]()
$886
This Flightnetwork deal was found by Cheapflights users on 2/11. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2812:45 pm
MDW
- MXP
2 stops14h 35m
Multiple Airlines
Sat 4/412:55 pm
MXP
- MDW
3 stops33h 25m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$887
This Delta deal was found by Cheapflights users on 2/8. 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.
Thu 8/131:00 pm
MDW
- LIN
2 stops15h 20m
Delta
Fri 8/216:25 am
LIN
- MDW
2 stops19h 06m
Delta
Deal found 2/8![Delta logo]()
$900
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:00 am
MDW
- MXP
1 stop20h 25m
Multiple Airlines
Tue 4/219:00 am
MXP
- MDW
2 stops20h 19m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$967
This KLM deal was found by Cheapflights users on 2/9. 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.
Mon 4/610:45 am
MDW
- MXP
1 stop15h 40m
KLM
Tue 4/2111:40 am
MXP
- MDW
1 stop17h 48m
KLM
Deal found 2/9![KLM logo]()
$970
This Delta deal was found by Cheapflights users on 2/9. 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 4/66:34 pm
MDW
- MXP
2 stops16h 01m
Delta
Tue 4/2111:40 am
MXP
- MDW
1 stop17h 48m
Delta
Deal found 2/9![Delta logo]()
$980
This KLM deal was found by Cheapflights users on 2/9. 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.
Mon 8/1710:35 am
MDW
- MXP
1 stop15h 50m
KLM
Mon 8/2411:40 am
MXP
- MDW
1 stop17h 06m
KLM
Deal found 2/9![KLM logo]()
$1,006
This Trip.com deal was found by Cheapflights users on 2/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:34 pm
MDW
- LIN
2 stops12h 21m
Air France
Tue 4/216:25 am
LIN
- MDW
2 stops17h 00m
Air France
Deal found 2/11![Air France logo]()
$1,037
This KLM deal was found by Cheapflights users on 2/10. 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.
Wed 4/1512:53 pm
MDW
- MXP
1 stop13h 32m
KLM
Tue 4/2811:40 am
MXP
- MDW
1 stop17h 48m
KLM
Deal found 2/10![KLM logo]()
$1,041
This Delta deal was found by Cheapflights users on 2/8. 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.
Wed 4/110:45 am
MDW
- LIN
2 stops15h 05m
Delta
Fri 4/106:40 am
LIN
- MDW
2 stops18h 14m
Delta
Deal found 2/8![Delta logo]()
$1,133
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 February 11, 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 February 11, 2026.
This Trip.com deal was found by Cheapflights users on 2/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:34 pm
MDW
- LIN
2 stops12h 21m
Air France
Tue 4/216:25 am
LIN
- MDW
2 stops17h 00m
Air France
Deal found 2/11![Air France logo]()
$1,037
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 3/1110:45 am
MDW
- MXP
2 stops16h 00m
Delta
Wed 3/1811:00 am
MXP
- MDW
2 stops17h 31m
Delta
Deal found 2/10![Delta logo]()
$1,085
This KLM deal was found by Cheapflights users on 2/10. 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.
Wed 3/1110:45 am
MDW
- MXP
1 stop15h 20m
KLM
Wed 3/1810:05 am
MXP
- MDW
1 stop18h 26m
KLM
Deal found 2/10![KLM logo]()
$1,206
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 3/1010:45 am
MDW
- MXP
1 stop15h 20m
Delta
Tue 3/1711:00 am
MXP
- MDW
2 stops17h 31m
Delta
Deal found 2/8![Delta logo]()
$1,085
This Delta deal was found by Cheapflights users on 2/10. 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.
Sat 4/186:00 am
MDW
- MXP
2 stops17h 45m
Delta
Sat 5/911:40 am
MXP
- MDW
1 stop16h 29m
Delta
Deal found 2/10![Delta logo]()
$1,091
This KLM deal was found by Cheapflights users on 2/8. 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.
Fri 4/1012:47 pm
MDW
- MXP
1 stop13h 38m
KLM
Sun 4/1911:40 am
MXP
- MDW
1 stop17h 48m
KLM
Deal found 2/8![KLM logo]()
$1,223
This Air France deal was found by Cheapflights users on 2/9. 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.
Mon 3/1612:47 pm
MDW
- MXP
1 stop13h 18m
Air France
Tue 4/1411:40 am
MXP
- MDW
1 stop17h 48m
Air France
Deal found 2/9![Air France logo]()
$1,226
This KLM deal was found by Cheapflights users on 2/9. 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 4/112:47 pm
MDW
- MXP
1 stop13h 38m
KLM
Fri 4/1011:40 am
MXP
- MDW
1 stop17h 51m
KLM
Deal found 2/9![KLM logo]()
$1,246
This Delta deal was found by Cheapflights users on 2/8. 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.
Wed 4/110:45 am
MDW
- LIN
2 stops15h 05m
Delta
Fri 4/106:40 am
LIN
- MDW
2 stops18h 14m
Delta
Deal found 2/8![Delta logo]()
$1,133
This KLM deal was found by Cheapflights users on 2/9. 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.
Sun 5/310:43 am
MDW
- MXP
1 stop15h 42m
KLM
Sat 5/1611:40 am
MXP
- MDW
1 stop16h 29m
KLM
Deal found 2/9![KLM logo]()
$1,254
This Delta deal was found by Cheapflights users on 2/10. 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 4/1010:45 am
MDW
- MXP
2 stops18h 20m
Delta
Sat 4/1811:40 am
MXP
- MDW
1 stop17h 48m
Delta
Deal found 2/10![Delta logo]()
$1,162
This Delta deal was found by Cheapflights users on 2/9. 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.
Sat 4/46:34 pm
MDW
- MXP
2 stops16h 01m
Delta
Thu 4/306:45 am
MXP
- MDW
2 stops18h 13m
Delta
Deal found 2/9![Delta logo]()
$1,196
This Trip.com deal was found by Cheapflights users on 2/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:20 pm
MDW
- LIN
2 stops13h 35m
KLM
Sun 4/196:40 am
LIN
- MDW
2 stops16h 49m
KLM
Deal found 2/10![KLM logo]()
$1,404
This Delta deal was found by Cheapflights users on 2/8. 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.
Thu 4/21:10 pm
MDW
- LIN
2 stops15h 10m
Delta
Tue 4/76:40 am
LIN
- MDW
2 stops19h 00m
Delta
Deal found 2/8![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/212:45 pm
MDW
- LIN
2 stops15h 30m
Delta
Sun 3/156:30 am
LIN
- MDW
2 stops17h 24m
Delta
Deal found 2/7![Delta logo]()
$1,635
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/251:49 pm
MDW
- LIN
2 stops14h 26m
Delta
Wed 3/46:30 am
LIN
- MDW
2 stops18h 07m
Delta
Deal found 2/7![Delta logo]()
$1,725
This Delta deal was found by Cheapflights users on 2/9. 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 5/106:36 pm
MDW
- LIN
2 stops14h 19m
Delta
Sun 5/176:40 am
LIN
- MDW
2 stops18h 34m
Delta
Deal found 2/9![Delta logo]()
$1,743
Last-minute flights from Midway to MilanDiscover last-minute flight deals from Midway to Milan. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Milan. Data last updated February 11, 2026 and is based on user searches.
This KLM deal was found by Cheapflights users on 2/11. 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.
Tue 3/310:49 am
MDW
- MXP
1 stop15h 16m
KLM
Wed 3/1810:05 am
MXP
- MDW
1 stop18h 26m
KLM
Deal found 2/11![KLM logo]()
$1,331
This Delta deal was found by Cheapflights users on 2/9. 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 3/91:10 pm
MDW
- MXP
2 stops13h 35m
Delta
Mon 3/168:30 am
MXP
- MDW
2 stops20h 01m
Delta
Deal found 2/9![Delta logo]()
$1,135
This Delta deal was found by Cheapflights users on 2/9. 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.
Wed 3/111:10 pm
MDW
- MXP
2 stops13h 35m
Delta
Wed 3/1811:00 am
MXP
- MDW
2 stops17h 31m
Delta
Deal found 2/9![Delta logo]()
$1,085
This KLM deal was found by Cheapflights users on 2/9. 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 3/1112:47 pm
MDW
- MXP
1 stop13h 18m
KLM
Wed 4/111:40 am
MXP
- MDW
1 stop17h 51m
KLM
Deal found 2/9![KLM logo]()
$1,206
This Delta deal was found by Cheapflights users on 2/9. 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.
Thu 3/121:10 pm
MDW
- MXP
2 stops13h 35m
Delta
Tue 3/319:00 am
MXP
- MDW
2 stops20h 31m
Delta
Deal found 2/9![Delta logo]()
$1,261
This Air France deal was found by Cheapflights users on 2/9. 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 3/1510:45 am
MDW
- MXP
1 stop15h 20m
Multiple Airlines
Wed 4/1511:40 am
MXP
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$1,081
This Delta deal was found by Cheapflights users on 2/9. 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 3/159:35 am
MDW
- MXP
2 stops17h 10m
Delta
Wed 4/1511:40 am
MXP
- MDW
1 stop17h 48m
Delta
Deal found 2/9![Delta logo]()
$1,086
This Air France deal was found by Cheapflights users on 2/9. 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 3/1510:45 am
MDW
- MXP
1 stop15h 20m
Multiple Airlines
Tue 4/1411:40 am
MXP
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$1,226
This KLM deal was found by Cheapflights users on 2/8. 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 3/1910:45 am
MDW
- MXP
1 stop15h 20m
KLM
Thu 3/2610:05 am
MXP
- MDW
1 stop18h 26m
KLM
Deal found 2/8![KLM logo]()
$1,131
This KLM deal was found by Cheapflights users on 2/11. 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 3/2310:45 am
MDW
- MXP
1 stop15h 20m
KLM
Mon 3/3011:40 am
MXP
- MDW
1 stop17h 51m
KLM
Deal found 2/11![KLM logo]()
$1,256
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2611:00 am
MDW
- MXP
2 stops15h 55m
Multiple Airlines
Thu 4/26:15 am
MXP
- MDW
3 stops34h 50m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$1,052
This Flightnetwork deal was found by Cheapflights users on 2/11. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2812:45 pm
MDW
- MXP
2 stops14h 35m
Multiple Airlines
Sat 4/412:55 pm
MXP
- MDW
3 stops33h 25m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$887
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 February 11, 2026.
Search for one-way flight options from Midway to Milan. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Tue 3/177:30 am
MDW
- MXP
3 stops27h 40m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sun 3/87:30 am
MDW
- MXP
2 stops25h 10m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sun 3/87:30 am
MDW
- LIN
2 stops44h 15m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:30 am
MDW
- MXP
3 stops26h 30m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Tue 3/177:30 am
MDW
- LIN
3 stops23h 55m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 3/107:30 am
MDW
- LIN
3 stops44h 10m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sun 3/299:30 am
MDW
- LIN
2 stops39h 20m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 3/157:30 am
MDW
- MXP
2 stops25h 10m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Fri 5/157:30 am
MDW
- LIN
3 stops43h 30m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$414
This Mytrip deal was found by Cheapflights users on 2/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:00 am
MDW
- LIN
3 stops21h 55m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$422
This Trip.com deal was found by Cheapflights users on 2/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:07 pm
MDW
- MXP
2 stops23h 08m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/289:16 pm
MDW
- MXP
3 stops44h 29m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$465
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $887 (Flightnetwork) |
One-way from | $299 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $594 |
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 February 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.
Fly from
Midway
Fly to
Milan
Route
Depart
Return
Price
ChicagoMilan
MDW - LIN
MDWLIN
Chicago Midway
Mon 4/6
6:34 pm-1:55 pm
2 stops12h 21m
Milan Linate
Tue 4/21
6:25 am-4:25 pm
2 stops17h 00m
$1,037
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 3/11
10:45 am-8:45 am
2 stops16h 00m
Milan Malpensa
Wed 3/18
11:00 am-10:31 pm
2 stops17h 31m
$1,085
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Tue 3/10
10:45 am-8:05 am
1 stop15h 20m
Milan Malpensa
Tue 3/17
11:00 am-10:31 pm
2 stops17h 31m
$1,085
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Sat 4/18
6:00 am-6:45 am
2 stops17h 45m
Milan Malpensa
Sat 5/9
11:40 am-9:09 pm
1 stop16h 29m
$1,091
ChicagoMilan
MDW - LIN
MDWLIN
Chicago Midway
Wed 4/1
10:45 am-8:50 am
2 stops15h 05m
Milan Linate
Fri 4/10
6:40 am-5:54 pm
2 stops18h 14m
$1,133
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Fri 4/10
10:45 am-12:05 pm
2 stops18h 20m
Milan Malpensa
Sat 4/18
11:40 am-10:28 pm
1 stop17h 48m
$1,162
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Sat 4/4
6:34 pm-5:35 pm
2 stops16h 01m
Milan Malpensa
Thu 4/30
6:45 am-5:58 pm
2 stops18h 13m
$1,196
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 3/11
10:45 am-8:05 am
1 stop15h 20m
Milan Malpensa
Wed 3/18
10:05 am-10:31 pm
1 stop18h 26m
$1,206
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Fri 4/10
12:47 pm-9:25 am
1 stop13h 38m
Milan Malpensa
Sun 4/19
11:40 am-10:28 pm
1 stop17h 48m
$1,223
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Mon 3/16
12:47 pm-8:05 am
1 stop13h 18m
Milan Malpensa
Tue 4/14
11:40 am-10:28 pm
1 stop17h 48m
$1,226
Showing 1-10 of 34 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Milan flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Milan flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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-MXP
MDW-LIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Milan
MDW-MIL
MDW-MXP
MDW-LIN
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 locationsMonza
Menaggio
Rho
Porlezza
Brescia
Novara
Assago
Bellagio
Stresa
Domodossola
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