$368+ 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 11/30. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Oct 20 — Oct 271
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 March or February, booked 39 days in advance, depart on a Friday or Saturday and return on a Tuesday
Cheap flight deals from Milan to Chicago
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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 September 20, 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 September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/1010:25 am -
1 stop13h 20m
Wed 11/187:15 pm -
1 stop19h 15m
Deal found 9/18![Multiple Airlines logo]()
$531
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/18:40 pm -
2 stops27h 05m
Sun 11/87:15 pm -
2 stops17h 40m
Deal found 9/17![Multiple Airlines logo]()
$545
This Mytrip deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Tue 11/37:25 am -
2 stops16h 20m
Tue 11/107:15 pm -
2 stops17h 25m
Deal found 9/19![Multiple Airlines logo]()
$546
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:15 am -
2 stops17h 00m
Wed 10/287:30 pm -
2 stops15h 30m
Deal found 9/16![Multiple Airlines logo]()
$649
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/87:25 pm -
3 stops28h 20m
Tue 11/247:15 pm -
1 stop16h 30m
Deal found 9/18![Multiple Airlines logo]()
$655
This lol.travel deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Thu 10/112:20 pm -
1 stop13h 23m
Wed 10/143:40 pm -
1 stop11h 40m
Deal found 9/17![Air Canada logo]()
$681
This lol.travel deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Thu 10/17:25 am -
1 stop14h 30m
Wed 10/147:05 pm -
1 stop11h 20m
Deal found 9/15![British Airways logo]()
$682
This lol.travel deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Mon 9/287:30 pm -
1 stop25h 20m
Thu 10/81:31 pm -
1 stop12h 34m
Deal found 9/17![British Airways logo]()
$682
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:15 am -
2 stops17h 00m
Sun 10/257:30 pm -
2 stops14h 00m
Deal found 9/18![Multiple Airlines logo]()
$684
This Bravofly deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:20 pm -
1 stop28h 59m
Sat 11/79:50 pm -
1 stop14h 05m
Deal found 9/20![British Airways logo]()
$688
This Booking.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/2211:20 am -
1 stop14h 55m
Sun 10/254:55 pm -
1 stop12h 10m
Deal found 9/18![Aer Lingus logo]()
$690
This lol.travel deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Thu 10/19:45 pm -
1 stop23h 05m
Wed 10/1410:30 pm -
1 stop15h 20m
Deal found 9/18![British Airways logo]()
$690
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 September 20, 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 September 20, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 1/1412:55 pm -
2 stops34h 50m
Mon 1/187:15 pm -
2 stops33h 50m
Deal found 9/15![Scandinavian Airlines logo]()
$689
This Finnair deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:45 pm -
1 stop24h 10m
Wed 10/148:50 pm -
1 stop17h 00m
Deal found 9/18![Multiple Airlines logo]()
$708
This SWISS deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:25 pm -
1 stop24h 10m
Fri 10/233:50 pm -
1 stop11h 00m
Deal found 9/19![SWISS logo]()
$711
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/309:15 am -
1 stop17h 50m
Fri 11/69:35 pm -
Nonstop8h 40m
Deal found 9/15![United Airlines logo]()
$712
This British Airways deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/1411:25 am -
1 stop14h 50m
Mon 1/184:29 pm -
2 stops16h 11m
Deal found 9/19![British Airways logo]()
$716
This Lufthansa deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:45 pm -
1 stop12h 20m
Sat 11/146:10 pm -
1 stop11h 30m
Deal found 9/20![Lufthansa logo]()
$722
This Austrian Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sat 10/103:00 pm -
1 stop29h 20m
Fri 10/2312:55 pm -
2 stops38h 00m
Deal found 9/19![Austrian Airlines logo]()
$729
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/16:40 am -
2 stops18h 53m
Wed 10/141:27 pm -
2 stops14h 53m
Deal found 9/17![Delta logo]()
$745
This KLM deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:40 am -
1 stop18h 04m
Wed 10/1412:49 pm -
1 stop13h 36m
Deal found 9/18![KLM logo]()
$843
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Tue 11/1011:20 am -
2 stops19h 41m
Wed 11/185:55 am -
1 stop18h 35m
Deal found 9/18![United Airlines logo]()
$713
This SWISS deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:40 am -
1 stop32h 55m
Tue 10/207:05 pm -
1 stop31h 45m
Deal found 9/17![SWISS logo]()
$713
This British Airways deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/19:45 pm -
1 stop23h 05m
Wed 10/141:31 pm -
1 stop12h 34m
Deal found 9/20![British Airways logo]()
$716
This Austrian Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Sun 10/187:00 am -
1 stop13h 20m
Wed 10/2112:55 pm -
2 stops37h 40m
Deal found 9/17![Austrian Airlines logo]()
$732
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/111:40 am -
1 stop18h 04m
Wed 10/1410:59 am -
1 stop15h 26m
Deal found 9/15![Delta logo]()
$749
This KLM deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/812:40 pm -
2 stops16h 53m
Mon 11/2311:27 am -
1 stop16h 18m
Deal found 9/15![Multiple Airlines logo]()
$753
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/1710:40 am -
1 stop32h 55m
Sat 10/2410:35 pm -
Nonstop8h 40m
Deal found 9/17![United Airlines logo]()
$715
This Austrian Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/227:00 am -
1 stop13h 20m
Thu 10/292:21 pm -
2 stops20h 04m
Deal found 9/16![Austrian Airlines logo]()
$733
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/86:30 am -
2 stops18h 30m
Mon 11/231:31 pm -
2 stops18h 24m
Deal found 9/15![Delta logo]()
$749
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/36:25 am -
1 stop11h 40m
Tue 12/86:10 pm -
1 stop15h 45m
Deal found 9/18![United Airlines logo]()
$716
This Austrian Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Mon 10/198:00 pm -
2 stops28h 05m
Wed 10/2112:55 pm -
2 stops37h 40m
Deal found 9/16![Austrian Airlines logo]()
$738
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/89:25 am -
2 stops36h 00m
Mon 11/235:40 pm -
1 stop16h 00m
Deal found 9/15![Multiple Airlines logo]()
$816
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/310:30 am -
1 stop12h 45m
Tue 12/83:15 pm -
1 stop12h 25m
Deal found 9/18![United Airlines logo]()
$717
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/306:30 am -
2 stops17h 30m
Fri 11/131:31 pm -
2 stops14h 44m
Deal found 9/16![Delta logo]()
$801
This KLM deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:40 am -
1 stop17h 53m
Tue 10/2010:59 am -
1 stop15h 26m
Deal found 9/17![KLM logo]()
$1,036
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:10 am -
2 stops35h 25m
Sat 10/244:05 pm -
2 stops16h 25m
Deal found 9/17![Multiple Airlines logo]()
$865
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/256:25 am -
1 stop11h 40m
Thu 1/282:25 pm -
2 stops15h 15m
Deal found 9/16![United Airlines logo]()
$720
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:30 am -
2 stops17h 09m
Tue 11/171:31 pm -
2 stops14h 44m
Deal found 9/18![Delta logo]()
$838
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Tue 12/156:25 am -
2 stops20h 27m
Sun 1/32:22 pm -
2 stops19h 33m
Deal found 9/19![United Airlines logo]()
$720
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/18:15 am -
2 stops17h 00m
Wed 10/143:45 pm -
1 stop14h 10m
Deal found 9/16![Multiple Airlines logo]()
$899
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/226:25 am -
2 stops18h 35m
Sun 10/256:44 pm -
2 stops13h 11m
Deal found 9/18![Delta logo]()
$844
Last-minute flights from Milan to ChicagoDiscover last-minute flight deals from Milan to Chicago. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Milan to Chicago. Data last updated September 20, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Mon 9/287:30 pm -
1 stop25h 20m
Thu 10/81:31 pm -
1 stop12h 34m
Deal found 9/17![British Airways logo]()
$682
This lol.travel deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Thu 10/112:20 pm -
1 stop13h 23m
Wed 10/143:40 pm -
1 stop11h 40m
Deal found 9/17![Air Canada logo]()
$681
This lol.travel deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Thu 10/19:45 pm -
1 stop23h 05m
Wed 10/1410:30 pm -
1 stop15h 20m
Deal found 9/18![British Airways logo]()
$690
This ResecentrumGruppen deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ResecentrumGruppen is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:20 pm -
1 stop14h 52m
Sun 10/112:01 pm -
1 stop13h 19m
Deal found 9/19![Air Canada logo]()
$691
This Kissandfly.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Thu 10/16:40 am -
1 stop14h 45m
Wed 10/144:55 pm -
1 stop19h 10m
Deal found 9/16![Multiple Airlines logo]()
$693
This ITA Airways deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Tue 10/65:00 pm -
1 stop27h 10m
Sun 10/113:00 pm -
1 stop12h 10m
Deal found 9/20![ITA Airways logo]()
$693
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:15 am -
2 stops17h 00m
Wed 10/287:30 pm -
2 stops15h 30m
Deal found 9/16![Multiple Airlines logo]()
$649
This lol.travel deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Thu 10/1511:05 am -
1 stop14h 10m
Sat 10/245:00 pm -
1 stop11h 05m
Deal found 9/18![British Airways logo]()
$692
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:15 am -
2 stops17h 00m
Sun 10/257:30 pm -
2 stops14h 00m
Deal found 9/18![Multiple Airlines logo]()
$684
This Booking.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/2211:20 am -
1 stop14h 55m
Sun 10/254:55 pm -
1 stop12h 10m
Deal found 9/18![Aer Lingus logo]()
$690
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2710:20 am -
1 stop15h 00m
Thu 11/53:55 pm -
1 stop17h 00m
Deal found 9/16![Multiple Airlines logo]()
$691
This Bravofly deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:20 pm -
1 stop28h 59m
Sat 11/79:50 pm -
1 stop14h 05m
Deal found 9/20![British Airways logo]()
$688
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 September 20, 2026.
Search for one-way flight options from Milan to Chicago. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/3010:10 pm -
2 stops49h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 2/229:20 pm -
2 stops28h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 12/18:05 pm -
2 stops27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 1/1412:20 pm -
2 stops36h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/610:15 pm -
2 stops25h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/229:25 am -
2 stops38h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 12/14:20 pm -
2 stops55h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 2/226:15 am -
3 stops41h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/169:15 pm -
2 stops27h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/3010:30 pm -
2 stops49h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/1712:20 pm -
2 stops36h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/314:50 pm -
2 stops54h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$406
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 September 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $531 (Kiwi.com) |
One-way from | $368 (Kiwi.com) |
Popular in | July |
Cheapest in | March |
Average price | $841 |
Good round-trip deal | $728 or less |
Good one-way deal | $788 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 September 20, 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
BergamoChicago
BGY Bergamo Orio Al Serio - ORD Chicago O'Hare Intl
BGYORD
Bergamo Orio Al Serio
Wed 12/16
8:30 pm-5:20 pm
3 stops27h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$435
BergamoChicago
BGY Bergamo Orio Al Serio - ORD Chicago O'Hare Intl
BGYORD
Bergamo Orio Al Serio
Thu 12/17
8:30 pm-5:20 pm
3 stops27h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$444
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
$460
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Wed 12/16
10:25 am-10:30 pm
1 stop19h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$479
BergamoChicago
BGY Bergamo Orio Al Serio - ORD Chicago O'Hare Intl
BGYORD
Bergamo Orio Al Serio
Tue 12/1
5:05 pm-2:55 pm
1 stop28h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$492
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Sat 10/24
9:20 am-9:15 pm
1 stop18h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$495
BergamoChicago
BGY Bergamo Orio Al Serio - ORD Chicago O'Hare Intl
BGYORD
Bergamo Orio Al Serio
Fri 11/13
8:40 am-5:20 pm
3 stops39h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$510
MilanChicago
LIN Milan Linate - ORD Chicago O'Hare Intl
LINORD
Milan Linate
Tue 12/1
9:20 pm-2:25 pm
1 stop24h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$522
MilanChicago
LIN Milan Linate - MDW Chicago Midway
LINMDW
Milan Linate
Mon 2/22
6:30 am-4:50 pm
2 stops17h 20m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$527
MilanChicago
MXP Milan Malpensa - MDW Chicago Midway
MXPMDW
Milan Malpensa
Mon 2/22
12:55 pm-10:10 pm
1 stop16h 15m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$527
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 September.
| 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
What is the cheapest month to book a flight from Milan to Chicago?
Currently, February is the cheapest month in which you can book a flight from Milan to Chicago (average of $686). Flying from Milan to Chicago in July is currently the most expensive (average of $1,033). 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 September 20, 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 September 20, 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 $676 and $922 in November.The cheapest round-trip price found within the last 5 days was $531 on Multiple Airlines (Nov 10-Nov 18).
How often are flights from Milan to Chicago delayed?
About 20% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 232 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 18% 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 36 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 September 20, 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
7.4
Food
6.7
Boarding
7.7
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.4
Food
6.7
Boarding
7.7
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.4
Food
6.7
Boarding
7.7
Crew
8.1
Comfort
7.3
Entertainment
7.1
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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