$361+ Cheap flights from Milan (MIL) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Dec 5 — Dec 121
Round-trip
1 adult, Economy
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Find cheap flights from Milan to Chicago 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 April, booked 4 days in advance, depart on a Tuesday or Saturday 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 November 5, 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 November 5, 2026.
This oojo deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:05 pm -
1 stop27h 40m
Sun 1/317:10 pm -
2 stops16h 30m
Deal found 11/2![Scandinavian Airlines logo]()
$596
This oojo deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:20 am -
1 stop12h 25m
Sun 1/317:10 pm -
2 stops16h 30m
Deal found 11/3![Scandinavian Airlines logo]()
$607
This FlightHub deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Thu 11/1911:20 am -
1 stop12h 25m
Mon 11/237:10 pm -
1 stop17h 05m
Deal found 11/4![Scandinavian Airlines logo]()
$632
This oojo deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:20 am -
1 stop12h 25m
Tue 1/57:10 pm -
1 stop32h 20m
Deal found 11/1![Scandinavian Airlines logo]()
$646
This Gotogate deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:05 pm -
1 stop27h 40m
Sun 11/227:10 pm -
1 stop32h 20m
Deal found 11/2![Scandinavian Airlines logo]()
$653
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:20 am -
1 stop12h 25m
Wed 11/257:10 pm -
1 stop17h 05m
Deal found 11/3![Scandinavian Airlines logo]()
$654
This lastminute.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:45 am -
1 stop13h 35m
Sun 11/223:55 pm -
1 stop12h 10m
Deal found 10/31![Aer Lingus logo]()
$658
This Booking.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:20 am -
1 stop16h 10m
Wed 2/107:00 pm -
1 stop21h 45m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$661
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2411:20 am -
1 stop12h 25m
Fri 1/17:10 pm -
1 stop30h 40m
Deal found 11/2![Scandinavian Airlines logo]()
$662
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Fri 12/1111:20 am -
1 stop12h 25m
Fri 1/17:10 pm -
1 stop30h 40m
Deal found 11/4![Scandinavian Airlines logo]()
$663
This Justfly.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:45 am -
1 stop13h 35m
Mon 11/233:55 pm -
1 stop12h 10m
Deal found 10/31![Aer Lingus logo]()
$678
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Fri 12/1112:55 pm -
2 stops34h 50m
Tue 1/57:10 pm -
2 stops57h 55m
Deal found 11/4![Scandinavian Airlines logo]()
$700
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 November 5, 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 November 5, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Fri 2/1911:20 am -
1 stop12h 25m
Tue 2/237:10 pm -
1 stop30h 40m
Deal found 11/4![Scandinavian Airlines logo]()
$647
This TAP AIR PORTUGAL deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/15:50 am -
1 stop17h 10m
Fri 5/215:45 pm -
1 stop23h 55m
Deal found 11/3![TAP AIR PORTUGAL logo]()
$808
This British Airways deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1012:40 pm -
1 stop13h 05m
Sun 1/318:30 pm -
1 stop14h 20m
Deal found 11/2![British Airways logo]()
$814
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/116:30 am -
1 stop14h 55m
Sun 2/141:10 pm -
2 stops15h 05m
Deal found 11/3![Delta logo]()
$843
This Austrian Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/18:05 pm -
1 stop24h 15m
Wed 4/74:20 pm -
1 stop19h 55m
Deal found 11/3![Austrian Airlines logo]()
$883
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/41:40 pm -
1 stop32h 40m
Sun 6/66:30 pm -
1 stop15h 55m
Deal found 10/31![United Airlines logo]()
$901
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Mon 12/1411:20 am -
1 stop12h 25m
Fri 1/17:10 pm -
1 stop30h 40m
Deal found 11/4![Scandinavian Airlines logo]()
$682
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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.
Mon 12/1412:55 pm -
2 stops34h 50m
Sun 1/107:10 pm -
2 stops33h 55m
Deal found 11/5![Scandinavian Airlines logo]()
$703
This British Airways deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/127:25 am -
1 stop13h 20m
Sun 3/78:40 pm -
1 stop14h 10m
Deal found 10/31![British Airways logo]()
$821
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 4/166:40 am -
1 stop14h 20m
Wed 4/2110:40 am -
2 stops15h 10m
Deal found 11/4![Delta logo]()
$843
This Scandinavian Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/241:00 pm -
2 stops34h 45m
Wed 3/106:00 am -
2 stops21h 30m
Deal found 11/2![Scandinavian Airlines logo]()
$713
This British Airways deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/117:25 am -
1 stop13h 20m
Sun 2/145:10 pm -
1 stop14h 20m
Deal found 11/3![British Airways logo]()
$824
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:55 am -
2 stops16h 20m
Sun 1/315:28 pm -
2 stops13h 27m
Deal found 11/2![Delta logo]()
$855
This Scandinavian Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/39:20 am -
2 stops31h 13m
Wed 4/287:15 pm -
1 stop12h 50m
Deal found 11/3![Scandinavian Airlines logo]()
$729
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
1 stop14h 55m
Mon 11/2310:35 am -
2 stops15h 10m
Deal found 10/31![Delta logo]()
$859
This Scandinavian Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/128:05 pm -
2 stops33h 26m
Sun 3/77:10 pm -
2 stops17h 05m
Deal found 10/31![Scandinavian Airlines logo]()
$737
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Fri 12/2511:20 am -
1 stop12h 25m
Sun 1/37:10 pm -
2 stops33h 10m
Deal found 11/4![Scandinavian Airlines logo]()
$754
This Scandinavian Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2411:20 am -
1 stop12h 25m
Sat 1/27:10 pm -
2 stops33h 40m
Deal found 10/31![Scandinavian Airlines logo]()
$757
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Thu 12/2411:20 am -
1 stop12h 25m
Sun 1/37:10 pm -
1 stop32h 20m
Deal found 11/4![Scandinavian Airlines logo]()
$761
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Fri 12/2511:20 am -
1 stop12h 25m
Mon 1/47:10 pm -
1 stop17h 05m
Deal found 11/4![Scandinavian Airlines logo]()
$809
Last-minute flights from Milan to ChicagoDiscover last-minute flight deals from Milan to Chicago. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Milan to Chicago. Data last updated November 5, 2026 and is based on user searches.
This lastminute.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:45 am -
1 stop13h 35m
Sun 11/223:55 pm -
1 stop12h 10m
Deal found 10/31![Aer Lingus logo]()
$658
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:20 am -
1 stop12h 25m
Wed 11/257:10 pm -
1 stop17h 05m
Deal found 11/3![Scandinavian Airlines logo]()
$654
This Gotogate deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:05 pm -
1 stop27h 40m
Sun 11/227:10 pm -
1 stop32h 20m
Deal found 11/2![Scandinavian Airlines logo]()
$653
This Booking.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:20 am -
1 stop16h 10m
Wed 2/107:00 pm -
1 stop21h 45m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$661
This FlightHub deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Thu 11/1911:20 am -
1 stop12h 25m
Mon 11/237:10 pm -
1 stop17h 05m
Deal found 11/4![Scandinavian Airlines logo]()
$632
This Justfly.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:45 am -
1 stop13h 35m
Mon 11/233:55 pm -
1 stop12h 10m
Deal found 10/31![Aer Lingus logo]()
$678
This oojo deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:20 am -
1 stop12h 25m
Sun 1/317:10 pm -
2 stops16h 30m
Deal found 11/3![Scandinavian Airlines logo]()
$607
This oojo deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:05 pm -
1 stop27h 40m
Sun 1/317:10 pm -
2 stops16h 30m
Deal found 11/2![Scandinavian Airlines logo]()
$596
This Scandinavian Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Fri 12/1112:55 pm -
2 stops34h 50m
Tue 1/57:10 pm -
2 stops57h 55m
Deal found 11/4![Scandinavian Airlines logo]()
$700
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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.
Sun 12/137:05 pm -
2 stops28h 40m
Tue 1/57:10 pm -
2 stops33h 55m
Deal found 11/5![Scandinavian Airlines logo]()
$703
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2411:20 am -
1 stop12h 25m
Fri 1/17:10 pm -
1 stop30h 40m
Deal found 11/2![Scandinavian Airlines logo]()
$662
This oojo deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:20 am -
1 stop12h 25m
Tue 1/57:10 pm -
1 stop32h 20m
Deal found 11/1![Scandinavian Airlines logo]()
$646
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 November 5, 2026.
Search for one-way flight options from Milan to Chicago. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/168:05 pm -
2 stops28h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/98:05 pm -
2 stops28h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/109:55 am -
2 stops40h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:25 pm -
2 stops31h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/69:30 pm -
2 stops26h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/148:00 pm -
2 stops26h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/119:50 pm -
2 stops26h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/269:25 pm -
2 stops24h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:40 pm -
3 stops47h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/3110:50 am -
2 stops35h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/278:05 pm -
2 stops28h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/105:35 pm -
3 stops54h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$408
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $555 (Icelandair) |
One-way from | $361 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $711 |
Good round-trip deal | $842 or less |
Good one-way deal | $822 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 7,457,451 searches. Data last updated November 5, 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 Milan Linate - ORD Chicago O'Hare Intl
LINORD
Milan Linate
Tue 11/24
4:55 pm-3:30 pm
2 stops29h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$432
MilanChicago
LIN Milan Linate - ORD Chicago O'Hare Intl
LINORD
Milan Linate
Tue 11/10
4:55 pm-3:30 pm
2 stops29h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$446
MilanChicago
LIN Milan Linate - ORD Chicago O'Hare Intl
LINORD
Milan Linate
Fri 11/20
11:20 am-3:30 pm
3 stops59h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$451
MilanChicago
LIN Milan Linate - ORD Chicago O'Hare Intl
LINORD
Milan Linate
Tue 1/26
7:15 am-3:30 pm
2 stops39h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$460
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Fri 11/20
10:35 pm-3:30 pm
3 stops47h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$461
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Thu 11/19
9:25 am-2:45 pm
1 stop36h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$482
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Sun 4/25
6:30 am-4:00 pm
1 stop16h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$493
MilanChicago
LIN Milan Linate - ORD Chicago O'Hare Intl
LINORD
Milan Linate
Thu 1/7
11:45 am-7:15 pm
1 stop14h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$496
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Tue 11/10
5:45 pm-3:30 pm
1 stop28h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$497
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Wed 1/13
10:25 am-10:27 pm
1 stop19h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$505
Showing 1-10 of 41 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
MXP-ORD
LIN-ORD
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
MXP-ORD
LIN-ORD
What is the cheapest month to book a flight from Milan to Chicago?
Currently, October is the cheapest month in which you can book a flight from Milan to Chicago (average of $729). Flying from Milan to Chicago in July is currently the most expensive (average of $1,043). 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 November 5, 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 November 5, 2026.
The most flights from MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Milan to Chicago?
Airfare is below average for this route at the moment.
Milan to Chicago flights typically cost between $618 and $1,063 in April.The cheapest round-trip price found within the last 5 days was $555 on Icelandair (Apr 17-May 17).
How often are flights from Milan to Chicago delayed?
About 17% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 231 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 Tuesday 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 13% of flights being delayed.
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 3 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 November 5, 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.
Overall
7.3
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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