$216+ Cheap flights from Chicago (CHI) to Milan (MIL)
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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Dec 6 — Dec 131
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Milan with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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 Chicago to Milan are usually found in January or February, booked 19 days in advance, depart on a Tuesday or Thursday and return on a Tuesday
Cheap flight deals from Chicago to Milan
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to MilanExplore the most affordable flight options available from Chicago to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2026.
Explore the most affordable flight options available from Chicago to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2026.
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm -
1 stop31h 55m
Tue 11/245:45 pm -
1 stop28h 45m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$718
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 12/86:30 pm -
1 stop14h 10m
Mon 12/146:10 am -
1 stop18h 10m
Deal found 11/2![Multiple Airlines logo]()
$719
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 12/267:30 pm -
1 stop30h 05m
Thu 1/148:00 pm -
2 stops26h 30m
Deal found 11/2![Multiple Airlines logo]()
$720
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/811:45 am -
1 stop14h 20m
Tue 11/246:50 pm -
1 stop22h 10m
Deal found 11/1![Turkish Airlines logo]()
$728
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm -
3 stops20h 35m
Tue 11/245:20 pm -
2 stops29h 10m
Deal found 11/1![Multiple Airlines logo]()
$730
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:55 pm -
2 stops16h 45m
Tue 11/249:05 am -
2 stops37h 25m
Deal found 11/2![Multiple Airlines logo]()
$736
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/307:10 pm -
1 stop17h 05m
Mon 12/711:20 am -
1 stop12h 25m
Deal found 11/3![Scandinavian Airlines logo]()
$740
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:00 pm -
1 stop21h 45m
Wed 11/186:20 am -
1 stop16h 10m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$742
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.
Mon 11/307:10 pm -
1 stop17h 05m
Sat 12/128:05 pm -
1 stop27h 40m
Deal found 11/1![Scandinavian Airlines logo]()
$746
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:30 pm -
3 stops33h 00m
Fri 12/47:50 pm -
3 stops28h 30m
Deal found 11/2![Multiple Airlines logo]()
$748
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.
Tue 12/297:10 pm -
2 stops17h 15m
Thu 1/1411:20 am -
1 stop12h 25m
Deal found 11/1![Scandinavian Airlines logo]()
$750
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm -
1 stop14h 50m
Tue 11/244:55 pm -
2 stops29h 35m
Deal found 11/1![Multiple Airlines logo]()
$752
Best flights from Chicago to MilanDiscover carefully curated flight deals from Chicago to Milan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 6, 2026.
Discover carefully curated flight deals from Chicago to Milan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 6, 2026.
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/108:15 pm -
1 stop34h 15m
Tue 1/196:50 pm -
1 stop22h 10m
Deal found 11/2![Turkish Airlines logo]()
$749
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.
Sat 1/97:10 pm -
1 stop32h 20m
Fri 1/2211:20 am -
1 stop12h 25m
Deal found 11/2![Scandinavian Airlines logo]()
$780
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.
Wed 1/136:25 pm -
1 stop12h 30m
Wed 1/2710:55 am -
1 stop34h 30m
Deal found 11/3![Delta logo]()
$822
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/243:45 pm -
1 stop11h 20m
Tue 1/1210:30 am -
1 stop12h 45m
Deal found 11/4![United Airlines logo]()
$861
This Austrian 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 Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:20 pm -
1 stop20h 30m
Wed 11/257:20 am -
1 stop13h 40m
Deal found 11/5![Austrian Airlines logo]()
$952
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.
Fri 12/257:10 pm -
1 stop30h 40m
Sat 1/1611:20 am -
1 stop12h 25m
Deal found 11/5![Scandinavian Airlines logo]()
$780
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.
Fri 1/157:10 pm -
2 stops33h 35m
Mon 1/2511:20 am -
1 stop12h 25m
Deal found 11/2![Scandinavian Airlines logo]()
$787
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:45 pm -
1 stop31h 00m
Thu 1/146:30 am -
1 stop14h 55m
Deal found 11/1![Delta logo]()
$868
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:05 pm -
1 stop15h 50m
Wed 1/136:25 am -
1 stop11h 40m
Deal found 11/5![United Airlines logo]()
$879
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.
Sun 1/317:10 pm -
2 stops16h 30m
Sun 2/71:45 pm -
2 stops34h 00m
Deal found 11/3![Scandinavian Airlines logo]()
$795
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.
Tue 1/129:50 am -
2 stops15h 55m
Sat 1/236:30 am -
1 stop14h 55m
Deal found 11/3![Delta logo]()
$876
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:05 pm -
1 stop15h 50m
Tue 1/126:25 am -
1 stop11h 40m
Deal found 11/5![United Airlines logo]()
$879
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.
Thu 12/247:10 pm -
1 stop30h 40m
Sat 1/1611:20 am -
1 stop12h 25m
Deal found 11/5![Scandinavian Airlines logo]()
$810
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 11/122:44 pm -
2 stops16h 11m
Wed 11/256:30 am -
1 stop14h 55m
Deal found 11/3![Delta logo]()
$920
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/94:20 pm -
1 stop13h 20m
Sun 1/246:25 am -
1 stop11h 40m
Deal found 11/2![United Airlines logo]()
$935
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.
Tue 12/297:10 pm -
1 stop17h 05m
Wed 1/138:05 pm -
1 stop27h 40m
Deal found 11/5![Scandinavian Airlines logo]()
$810
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:25 pm -
1 stop10h 35m
Sat 1/161:00 pm -
1 stop32h 25m
Deal found 11/5![Delta logo]()
$921
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.
Thu 12/247:10 pm -
2 stops58h 45m
Wed 1/138:05 pm -
1 stop27h 40m
Deal found 11/5![Scandinavian Airlines logo]()
$814
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:00 am -
2 stops14h 45m
Sat 1/96:30 am -
2 stops19h 46m
Deal found 11/1![Delta logo]()
$931
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 1/3010:40 am -
2 stops16h 50m
Sat 2/610:05 pm -
1 stop25h 40m
Deal found 11/3![Scandinavian Airlines logo]()
$835
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:25 pm -
1 stop12h 30m
Sat 12/1910:55 am -
2 stops16h 33m
Deal found 11/1![Delta logo]()
$995
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2910:40 am -
2 stops25h 35m
Sun 2/711:20 am -
1 stop12h 25m
Deal found 11/1![Scandinavian Airlines logo]()
$851
Last-minute flights from Chicago to MilanDiscover last-minute flight deals from Chicago to Milan. Data last updated November 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Milan. Data last updated November 6, 2026 and is based on user searches.
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm -
1 stop31h 55m
Tue 11/245:45 pm -
1 stop28h 45m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$718
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/811:45 am -
1 stop14h 20m
Tue 11/246:50 pm -
1 stop22h 10m
Deal found 11/1![Turkish Airlines logo]()
$728
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm -
3 stops20h 35m
Tue 11/245:20 pm -
2 stops29h 10m
Deal found 11/1![Multiple Airlines logo]()
$730
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm -
1 stop20h 25m
Wed 11/186:20 am -
1 stop16h 10m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$742
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm -
1 stop14h 50m
Tue 11/244:55 pm -
2 stops29h 35m
Deal found 11/1![Multiple Airlines logo]()
$752
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:55 pm -
2 stops16h 45m
Tue 11/249:05 am -
2 stops37h 25m
Deal found 11/2![Multiple Airlines logo]()
$736
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/307:10 pm -
1 stop17h 05m
Mon 12/711:20 am -
1 stop12h 25m
Deal found 11/3![Scandinavian Airlines logo]()
$740
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.
Mon 11/307:10 pm -
1 stop17h 05m
Sat 12/128:05 pm -
1 stop27h 40m
Deal found 11/1![Scandinavian Airlines logo]()
$746
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:30 pm -
3 stops33h 00m
Fri 12/47:50 pm -
3 stops28h 30m
Deal found 11/2![Multiple Airlines logo]()
$748
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 12/86:30 pm -
1 stop14h 10m
Mon 12/146:10 am -
1 stop18h 10m
Deal found 11/2![Multiple Airlines logo]()
$719
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 12/267:30 pm -
1 stop30h 05m
Thu 1/148:00 pm -
2 stops26h 30m
Deal found 11/2![Multiple Airlines logo]()
$720
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.
Tue 12/297:10 pm -
2 stops17h 15m
Thu 1/1411:20 am -
1 stop12h 25m
Deal found 11/2![Scandinavian Airlines logo]()
$750
One-way flights from Chicago to MilanSearch for one-way flight options from Chicago to Milan. Find affordable one-way fares based on user searches. Data last updated November 6, 2026.
Search for one-way flight options from Chicago to Milan. Find affordable one-way fares based on user searches. Data last updated November 6, 2026.
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:00 pm -
1 stop14h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$216
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/278:10 pm -
1 stop20h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$222
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 11/257:00 pm -
1 stop21h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![TAP AIR PORTUGAL logo]()
$223
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 11/117:00 pm -
2 stops22h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$256
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 11/257:00 pm -
2 stops21h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$273
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.
Sun 11/298:10 pm -
2 stops42h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$273
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.
Fri 11/278:10 pm -
2 stops19h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$279
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 11/257:00 pm -
2 stops19h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$294
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 11/117:00 pm -
2 stops19h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$302
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.
Sun 11/298:10 pm -
3 stops21h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$306
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:25 pm -
3 stops34h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$312
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.
Fri 11/278:10 pm -
2 stops19h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$312
Find flight deals from Chicago to Milan
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 November 6, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $714 (oojo) |
One-way from | $216 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $776 |
Good round-trip deal | $1,195 or less |
Good one-way deal | $774 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 7,457,451 searches. Data last updated November 6, 2026.
Use the filters below to find and compare flights from Chicago to Milan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Fri 11/27
8:10 pm-10:10 pm
2 stops19h 00m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$312
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Sat 11/28
6:30 pm-8:40 pm
3 stops19h 10m
Milan Malpensa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$430
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Sun 11/29
8:10 pm-6:00 pm
1 stop14h 50m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$469
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Tue 1/5
7:10 pm-10:30 am
1 stop32h 20m
Milan Malpensa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$557
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Tue 12/8
11:45 am-4:50 pm
1 stop22h 05m
Milan Malpensa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$571
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Mon 11/30
3:55 pm-11:05 am
1 stop12h 10m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$583
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Mon 12/7
6:25 pm-7:20 pm
1 stop17h 55m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$612
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Tue 12/8
6:25 pm-1:55 pm
1 stop12h 30m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$612
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Mon 12/7
8:50 am-11:45 am
2 stops19h 55m
Milan Malpensa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$617
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Sun 12/27
1:26 pm-11:45 am
2 stops15h 19m
Milan Malpensa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$617
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Chicago 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 Chicago to Milan in November.
| 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 | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Milan flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Milan flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-Milan flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Milan flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-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 Chicago to Milan
Have a flexible travel schedule? Discover the best time to fly to Milan from Chicago with our price prediction graph.
CHI-MIL
ORD-MXP
ORD-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 to Milan
CHI-MIL
ORD-MXP
ORD-LIN
What is the cheapest month to book a flight from Chicago to Milan?
Currently, February is the cheapest month in which you can book a flight from Chicago to Milan (average of $577). Flying from Chicago to Milan in June is currently the most expensive (average of $1,363). 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 CHI to MIL?
Find hourly flight availability from Chicago to Milan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 6, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Milan as you normally would.
Weekly flight availability from Chicago to Milan
Explore weekly flight availability from Chicago to Milan. 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 6, 2026.
The most flights from CHI to MIL 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 Chicago to Milan?
Airfare is typical for this route at the moment.
Chicago to Milan flights typically cost between $648 and $934 in April.The cheapest round-trip price found within the last 5 days was $714 on Scandinavian Airlines (Apr 9-Apr 17).
What’s the top layover airport for flights from Chicago to Milan?
Share of 1-stop round-trip flights from Chicago to Milan chosen by Cheapflights users in the past 12 months, using the same layover each way.
Copenhagen (CPH) – chosen by Cheapflights users on 57% of 1-stop itineraries from Chicago to Milan on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Milan?
Average round-trip fare for 1-stop flights from Chicago to Milan, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Frankfurt am Main (FRA) is the most affordable 1-stop option, with an average round-trip price of $585.
What’s the fastest layover option from Chicago to Milan?
Shortest average travel time for 1-stop one-way flights from Chicago to Milan, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Copenhagen (CPH) have the shortest average one-way travel time for 1-stop routes: 11h 55m.
Which airport typically offers the quickest layover for flights from Chicago to Milan?
Average layover duration for 1-stop one-way flights from Chicago to Milan, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Copenhagen (CPH) offer the fastest connection on this route, with an average layover time of 1h 53m.
How far ahead should I book a flight from Chicago to Milan?
The price you pay for your flight from Chicago to Milan may vary depending on when you book. For the best chance of a lower fare, look to book 7 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
The best insider tips for Chicago to Milan 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 Chicago to Milan trip
Our travel experts
Reviews of airlines servicing Milan
Get insights into the airlines that provide service to Milan. 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 Milan. Reviews last updated November 6, 2026.
Read through reviews of airlines operating flights from Chicago to Milan, such as Scandinavian Airlines,Aer Lingus, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Overall
7.5
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Entertainment
6.8
Overall
7.5
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Entertainment
6.8
Overall
7.5
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Entertainment
6.8
Overall
7.5
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Entertainment
6.8
Overall
7.5
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Entertainment
6.8
Overall
7.5
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 locationsRho
Brescia
Porlezza
Assago
Stresa
Domodossola
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Top 7 airlines flying from Chicago to Milan
Discover the top 7 airlines that operate flights from Chicago to Milan. 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 7,457,451 searches. Data last updated November 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$402 | Average$711 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$453 | Average$663 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$564 | Average$809 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$630 | Average$654 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$779 | Average$1,131 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$780 | Average$1,243 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$823 | Average$1,227 | FlexibilityNo cancel fee | On-time76% |