$373+ Cheap flights from Milan (MIL) to Chicago (CHI)
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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
mai 27 — juin 31
Round-trip
1 adult, Economy
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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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Milan to Chicago are usually found in February or March, booked 63 days in advance, depart on a Saturday or Tuesday and return on a Tuesday
Cheap flight deals from Milan to Chicago
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Best
Last-minute
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Cheapest flights from Milan to ChicagoExplore the most affordable flight options available from Milan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on avril 27, 2026.
Explore the most affordable flight options available from Milan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on avril 27, 2026.
This Mytrip deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/210:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
dim. 6/77:25 pm
ORD
- MXP
1 stop12h 45m
Icelandair
Deal found 4/24![Icelandair logo]()
$535
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/910:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
lun. 6/1510:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 4/26![Icelandair logo]()
$536
This Mytrip deal was found by Cheapflights users on 4/27. 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.
mar. 6/910:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
mar. 6/1610:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/27![Icelandair logo]()
$537
This FlightHub deal was found by Cheapflights users on 4/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/234:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
sam. 5/3010:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$545
This FlightHub deal was found by Cheapflights users on 4/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/214:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
sam. 5/3010:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$546
This lol.travel deal was found by Cheapflights users on 4/24. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/17:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
lun. 6/293:00 pm
ORD
- LIN
1 stop12h 10m
ITA Airways
Deal found 4/24![ITA Airways logo]()
$554
This Icelandair deal was found by Cheapflights users on 4/25. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/184:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
mar. 5/2610:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$567
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
jeu. 5/214:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
mar. 5/2610:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$568
This Icelandair deal was found by Cheapflights users on 4/25. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/2210:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
sam. 5/3010:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$569
This Flighttix deal was found by Cheapflights users on 4/24. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/84:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
lun. 6/157:25 pm
ORD
- MXP
1 stop19h 30m
Icelandair
Deal found 4/24![Icelandair logo]()
$571
This lol.travel deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/108:00 pm
LIN
- ORD
1 stop24h 10m
ITA Airways
lun. 5/253:00 pm
ORD
- LIN
1 stop23h 10m
ITA Airways
Deal found 4/23![ITA Airways logo]()
$585
This lol.travel deal was found by Cheapflights users on 4/24. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/89:00 pm
LIN
- ORD
1 stop23h 10m
ITA Airways
dim. 10/113:00 pm
ORD
- LIN
1 stop12h 10m
ITA Airways
Deal found 4/24![ITA Airways logo]()
$604
Best flights from Milan to ChicagoDiscover carefully curated flight deals from Milan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated avril 27, 2026.
Discover carefully curated flight deals from Milan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated avril 27, 2026.
This British Airways deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/107:25 am
LIN
- ORD
2 stops16h 39m
British Airways
lun. 5/257:05 pm
ORD
- LIN
1 stop11h 30m
British Airways
Deal found 4/23![British Airways logo]()
$685
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
mer. 5/209:00 am
MXP
- MDW
2 stops19h 09m
Delta
mer. 5/271:59 pm
MDW
- MXP
2 stops17h 46m
Delta
Deal found 4/23![Delta logo]()
$694
This Mytrip deal was found by Cheapflights users on 4/25. 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.
mar. 5/265:55 am
BGY
- ORD
2 stops21h 00m
Multiple Airlines
mar. 6/29:55 am
ORD
- BGY
2 stops24h 45m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$815
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/243:20 pm
MXP
- ORD
Nonstop9h 45m
United Airlines
sam. 10/3110:50 pm
ORD
- MXP
1 stop11h 50m
United Airlines
Deal found 4/26![United Airlines logo]()
$831
This Austrian Airlines deal was found by Cheapflights users on 4/26. 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 Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/28:00 pm
LIN
- ORD
1 stop24h 20m
Austrian Airlines
mer. 9/301:12 pm
ORD
- LIN
2 stops37h 23m
Austrian Airlines
Deal found 4/26![Austrian Airlines logo]()
$843
This Scandinavian Airlines deal was found by Cheapflights users on 4/25. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/2511:25 am
MXP
- ORD
1 stop11h 45m
Scandinavian Airlines
ven. 6/57:00 am
ORD
- MXP
2 stops20h 35m
Scandinavian Airlines
Deal found 4/25![Scandinavian Airlines logo]()
$851
This ITA Airways deal was found by Cheapflights users on 4/26. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/229:00 pm
LIN
- ORD
1 stop23h 10m
ITA Airways
lun. 6/13:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Deal found 4/26![ITA Airways logo]()
$858
This KLM deal was found by Cheapflights users on 4/25. 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.
jeu. 10/811:40 am
MXP
- MDW
1 stop17h 05m
KLM
lun. 10/121:05 pm
MDW
- MXP
1 stop13h 20m
KLM
Deal found 4/25![KLM logo]()
$907
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
jeu. 10/111:40 am
MXP
- MDW
1 stop17h 06m
Delta
jeu. 10/151:05 pm
MDW
- MXP
2 stops16h 00m
Delta
Deal found 4/23![Delta logo]()
$709
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dim. 5/106:40 am
LIN
- MDW
2 stops18h 53m
Delta
mar. 5/267:13 pm
MDW
- LIN
2 stops13h 42m
Delta
Deal found 4/23![Delta logo]()
$711
This Mytrip deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/810:05 pm
BGY
- ORD
3 stops23h 45m
Multiple Airlines
lun. 6/158:45 am
ORD
- BGY
2 stops25h 55m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$816
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
sam. 5/166:45 am
MXP
- ORD
2 stops17h 35m
Delta
mar. 5/266:07 am
ORD
- MXP
1 stop17h 38m
Delta
Deal found 4/23![Delta logo]()
$712
This United Airlines deal was found by Cheapflights users on 4/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/2610:35 am
LIN
- ORD
2 stops19h 55m
United Airlines
mar. 6/22:21 pm
ORD
- LIN
2 stops17h 19m
United Airlines
Deal found 4/25![United Airlines logo]()
$876
This ITA Airways deal was found by Cheapflights users on 4/25. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/159:00 pm
LIN
- ORD
1 stop23h 10m
ITA Airways
dim. 7/193:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Deal found 4/25![ITA Airways logo]()
$895
This Mytrip deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/93:05 pm
BGY
- ORD
2 stops28h 30m
Multiple Airlines
lun. 5/252:15 pm
ORD
- BGY
2 stops25h 50m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$837
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dim. 5/106:45 am
MXP
- ORD
2 stops18h 04m
Delta
lun. 5/256:07 am
ORD
- MXP
1 stop17h 38m
Delta
Deal found 4/23![Delta logo]()
$712
This Austrian Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/2010:25 am
LIN
- ORD
2 stops34h 45m
Austrian Airlines
mer. 5/274:30 pm
ORD
- LIN
2 stops34h 05m
Austrian Airlines
Deal found 4/23![Austrian Airlines logo]()
$951
This KLM deal was found by Cheapflights users on 4/26. 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.
mar. 6/911:40 am
MXP
- MDW
1 stop17h 37m
KLM
lun. 6/1511:05 am
MDW
- MXP
1 stop15h 20m
KLM
Deal found 4/26![KLM logo]()
$953
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/83:20 pm
MXP
- ORD
Nonstop9h 40m
United Airlines
mar. 5/123:40 pm
ORD
- MXP
1 stop11h 40m
United Airlines
Deal found 4/23![United Airlines logo]()
$878
This Scandinavian Airlines deal was found by Cheapflights users on 4/26. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/227:50 pm
MXP
- ORD
2 stops27h 20m
Scandinavian Airlines
lun. 6/17:00 am
ORD
- MXP
2 stops20h 35m
Scandinavian Airlines
Deal found 4/26![Scandinavian Airlines logo]()
$972
This British Airways deal was found by Cheapflights users on 4/24. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/207:40 pm
LIN
- ORD
1 stop25h 10m
British Airways
lun. 6/17:05 pm
ORD
- LIN
1 stop13h 00m
British Airways
Deal found 4/24![British Airways logo]()
$976
This Austrian Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/108:00 pm
LIN
- ORD
2 stops28h 20m
Austrian Airlines
mar. 5/264:20 pm
ORD
- LIN
1 stop14h 50m
Austrian Airlines
Deal found 4/23![Austrian Airlines logo]()
$951
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
sam. 8/156:25 pm
BGY
- ORD
1 stop24h 25m
Multiple Airlines
mar. 8/259:00 pm
ORD
- BGY
2 stops17h 05m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$883
This Delta deal was found by Cheapflights users on 4/26. 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.
sam. 5/166:40 am
LIN
- MDW
2 stops18h 53m
Delta
mar. 5/266:36 pm
MDW
- LIN
2 stops14h 19m
Delta
Deal found 4/26![Delta logo]()
$746
This British Airways deal was found by Cheapflights users on 4/27. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/177:25 am
LIN
- ORD
1 stop13h 25m
British Airways
mar. 8/257:05 pm
ORD
- LIN
1 stop11h 25m
British Airways
Deal found 4/27![British Airways logo]()
$1,015
This Mytrip deal was found by Cheapflights users on 4/25. 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.
mar. 6/96:05 am
BGY
- ORD
2 stops21h 00m
Multiple Airlines
mar. 6/169:55 am
ORD
- BGY
3 stops24h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$901
This United Airlines deal was found by Cheapflights users on 4/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/203:20 pm
MXP
- ORD
Nonstop9h 40m
United Airlines
mer. 5/279:40 pm
ORD
- MXP
Nonstop8h 40m
United Airlines
Deal found 4/25![United Airlines logo]()
$1,006
This Delta deal was found by Cheapflights users on 4/27. 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.
jeu. 10/86:40 am
LIN
- MDW
2 stops18h 57m
Delta
mar. 10/135:35 pm
MDW
- LIN
2 stops15h 20m
Delta
Deal found 4/27![Delta logo]()
$800
This Condor deal was found by Cheapflights users on 4/26. 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.
mar. 6/97:00 am
MXP
- MDW
2 stops19h 20m
Multiple Airlines
lun. 6/159:20 am
MDW
- MXP
2 stops29h 00m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$911
This United Airlines deal was found by Cheapflights users on 4/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 8/233:20 pm
MXP
- ORD
Nonstop9h 50m
United Airlines
lun. 8/313:35 pm
ORD
- MXP
1 stop18h 05m
United Airlines
Deal found 4/27![United Airlines logo]()
$1,028
Last-minute flights from Milan to ChicagoDiscover last-minute flight deals from Milan to Chicago. Data last updated avril 27, 2026 and is based on user searches.
Discover last-minute flight deals from Milan to Chicago. Data last updated avril 27, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 4/24. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/69:00 pm
LIN
- ORD
1 stop23h 10m
ITA Airways
lun. 5/113:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Deal found 4/24![ITA Airways logo]()
$610
This lol.travel deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/108:00 pm
LIN
- ORD
1 stop24h 10m
ITA Airways
lun. 5/253:00 pm
ORD
- LIN
1 stop23h 10m
ITA Airways
Deal found 4/23![ITA Airways logo]()
$585
This lol.travel deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/107:25 am
LIN
- ORD
1 stop14h 30m
British Airways
mar. 5/265:00 pm
ORD
- LIN
1 stop12h 30m
British Airways
Deal found 4/22![British Airways logo]()
$638
This Gotogate deal was found by Cheapflights users on 4/25. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/154:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
ven. 5/2910:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$589
This Icelandair deal was found by Cheapflights users on 4/24. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/164:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
mar. 5/2610:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/24![Icelandair logo]()
$611
This Icelandair deal was found by Cheapflights users on 4/25. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/184:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
mar. 5/2610:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$567
This Icelandair deal was found by Cheapflights users on 4/25. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/184:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
ven. 5/2910:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$627
This FlightHub deal was found by Cheapflights users on 4/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/214:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
sam. 5/3010:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
jeu. 5/214:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
mar. 5/2610:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$568
This FlightHub deal was found by Cheapflights users on 4/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/214:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
ven. 5/2910:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$606
This Icelandair deal was found by Cheapflights users on 4/25. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/2210:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
sam. 5/3010:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$569
This FlightHub deal was found by Cheapflights users on 4/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/234:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
sam. 5/3010:25 pm
ORD
- MXP
1 stop33h 45m
Icelandair
Deal found 4/25![Icelandair logo]()
$545
One-way flights from Milan to ChicagoSearch for one-way flight options from Milan to Chicago. Find affordable one-way fares based on user searches. Data last updated avril 27, 2026.
Search for one-way flight options from Milan to Chicago. Find affordable one-way fares based on user searches. Data last updated avril 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
mer. 5/136:45 am
BGY
- ORD
2 stops41h 09m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$373
This Mytrip deal was found by Cheapflights users on 4/27. 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.
ven. 8/2110:55 pm
MXP
- ORD
1 stop29h 30m
Icelandair
Deal found 4/27![Icelandair logo]()
$378
This Mytrip deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
mar. 9/294:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 4/22![Icelandair logo]()
$383
This oojo deal was found by Cheapflights users on 4/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 9/134:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 4/27![Icelandair logo]()
$386
This Booking.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 6/74:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 4/22![Icelandair logo]()
$387
This FlightHub deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/84:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 4/23![Icelandair logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/66:00 am
BGY
- ORD
2 stops18h 50m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
jeu. 10/88:10 am
MXP
- ORD
2 stops40h 40m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
mer. 9/3011:55 pm
MXP
- ORD
3 stops24h 55m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/1411:15 pm
MXP
- ORD
2 stops31h 41m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$403
This Air Serbia deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/99:20 am
MXP
- ORD
1 stop18h 55m
Air Serbia
Deal found 4/25![Air Serbia logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/99:35 pm
MXP
- ORD
2 stops27h 15m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$405
Find flight deals from Milan to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Milan (MIL) to Chicago (CHI). 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 avril 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $535 (Mytrip) |
One-way from | $373 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $771 |
Good round-trip deal | $655 or less |
Good one-way deal | $990 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Milan to Chicago 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 avril 27, 2026.
Use the filters below to find and compare flights from Milan to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilanChicago
LIN - ORD
LINORD
Milan Linate
dim. 5/10
7:25 am-5:04 pm
2 stops16h 39m
Chicago O'Hare Intl
lun. 5/25
7:05 pm-1:35 pm
1 stop11h 30m
$685
MilanChicago
MXP - MDW
MXPMDW
Milan Malpensa
mer. 5/20
9:00 am-9:09 pm
2 stops19h 09m
Chicago Midway
mer. 5/27
1:59 pm-2:45 pm
2 stops17h 46m
$694
MilanChicago
MXP - MDW
MXPMDW
Milan Malpensa
jeu. 10/1
11:40 am-9:46 pm
1 stop17h 06m
Chicago Midway
jeu. 10/15
1:05 pm-12:05 pm
2 stops16h 00m
$709
MilanChicago
LIN - MDW
LINMDW
Milan Linate
dim. 5/10
6:40 am-6:33 pm
2 stops18h 53m
Chicago Midway
mar. 5/26
7:13 pm-3:55 pm
2 stops13h 42m
$711
MilanChicago
MXP - ORD
MXPORD
Milan Malpensa
sam. 5/16
6:45 am-5:20 pm
2 stops17h 35m
Chicago O'Hare Intl
mar. 5/26
6:07 am-6:45 am
1 stop17h 38m
$712
MilanChicago
MXP - ORD
MXPORD
Milan Malpensa
dim. 5/10
6:45 am-5:49 pm
2 stops18h 04m
Chicago O'Hare Intl
lun. 5/25
6:07 am-6:45 am
1 stop17h 38m
$712
MilanChicago
LIN - MDW
LINMDW
Milan Linate
sam. 5/16
6:40 am-6:33 pm
2 stops18h 53m
Chicago Midway
mar. 5/26
6:36 pm-3:55 pm
2 stops14h 19m
$746
MilanChicago
LIN - MDW
LINMDW
Milan Linate
jeu. 10/8
6:40 am-6:37 pm
2 stops18h 57m
Chicago Midway
mar. 10/13
5:35 pm-3:55 pm
2 stops15h 20m
$800
BergamoChicago
BGY - ORD
BGYORD
Bergamo Orio Al Serio
mar. 5/26
5:55 am-7:55 pm
2 stops21h 00m
Chicago O'Hare Intl
mar. 6/2
9:55 am-5:40 pm
2 stops24h 45m
$815
BergamoChicago
BGY - ORD
BGYORD
Bergamo Orio Al Serio
lun. 6/8
10:05 pm-2:50 pm
3 stops23h 45m
Chicago O'Hare Intl
lun. 6/15
8:45 am-5:40 pm
2 stops25h 55m
$816
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Milan to Chicago
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 Milan to Chicago in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Milan-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milan-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milan-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Milan-Chicago 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 Milan-Chicago 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 Milan to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Milan with our price prediction graph.
MIL-CHI
BGY-ORD
MXP-ORD
LIN-ORD
LIN-MDW
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 Milan to Chicago
MIL-CHI
BGY-ORD
MXP-ORD
LIN-ORD
LIN-MDW
How far ahead should I book a flight from Milan to Chicago?
The price you pay for your flight from Milan to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 57 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Milan to Chicago?
Currently, September is the cheapest month in which you can book a flight from Milan to Chicago (average of $356). Flying from Milan to Chicago in July is currently the most expensive (average of $615). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MIL to CHI?
Find hourly flight availability from Milan to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated avril 27, 2026.
When flying from Milan to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Milan to Chicago
Explore weekly flight availability from Milan to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated avril 27, 2026.
The most flights from MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Milan to Chicago?
How often are flights from Milan to Chicago delayed?
About 22% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 208 minutes.
What is the most punctual flight time for Milan to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Friday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Milan to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 21% of flights being delayed.
The best insider tips for Milan to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Milan to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated avril 27, 2026.
Get a feel of what it's like to fly with United Airlines and Lufthansa from Milan to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.6
Crew
8.1
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Food
6.6
Crew
8.1
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Food
6.6
Crew
8.1
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Related info for your journey
Find useful and relevant information for your journey from Milan to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on avril 27, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milan to Chicago by cabin class
Find flights from Milan to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milan and Chicago flights
Browse other Milan and Chicago flight options. Last updated on avril 27, 2026.
Other flights from Milan
Browse through other flights departing from Milan. Flights are based on user searches made on Cheapflights and were last updated on avril 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Milan to Chicago
Discover the top airline that operate flights from Milan to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated avril 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$695 | Average$933 | FlexibilityNo cancel fee | On-time69% |