$282+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Oct 17 — Oct 241
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 February or January, booked 7 days in advance, depart on a Tuesday or Monday and return on a Friday
Cheap flight deals from Chicago to Milan
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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 September 17, 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 September 17, 2026.
This Mytrip deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:30 pm -
2 stops23h 15m
Wed 11/46:00 am -
2 stops18h 20m
Deal found 9/13![Multiple Airlines logo]()
$588
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/197:25 pm -
2 stops19h 25m
Wed 10/288:55 am -
2 stops15h 25m
Deal found 9/14![Multiple Airlines logo]()
$613
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Fri 11/68:10 pm -
2 stops19h 05m
Sat 11/142:45 pm -
2 stops31h 45m
Deal found 9/14![Multiple Airlines logo]()
$615
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 11/56:30 pm -
2 stops23h 00m
Sun 11/88:50 pm -
2 stops27h 30m
Deal found 9/16![Multiple Airlines logo]()
$617
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
2 stops18h 10m
Wed 10/216:45 am -
2 stops20h 03m
Deal found 9/14![Multiple Airlines logo]()
$661
This Mytrip deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/254:55 pm -
3 stops34h 25m
Tue 11/106:40 am -
2 stops18h 40m
Deal found 9/13![Multiple Airlines logo]()
$664
This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/254:55 pm -
1 stop12h 10m
Tue 11/1011:45 am -
1 stop13h 35m
Deal found 9/13![Aer Lingus logo]()
$664
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Mon 10/193:45 pm -
1 stop11h 55m
Wed 10/2811:45 am -
1 stop13h 35m
Deal found 9/14![Aer Lingus logo]()
$665
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/197:25 pm -
2 stops35h 35m
Wed 10/287:20 am -
1 stop17h 00m
Deal found 9/14![Multiple Airlines logo]()
$669
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/228:10 pm -
1 stop20h 25m
Tue 12/15:45 pm -
1 stop28h 45m
Deal found 9/12![TAP AIR PORTUGAL logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/269:05 pm -
1 stop19h 55m
Tue 11/310:20 am -
1 stop15h 00m
Deal found 9/13![Multiple Airlines logo]()
$673
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Fri 11/68:10 pm -
3 stops30h 10m
Sat 11/141:10 pm -
2 stops33h 20m
Deal found 9/14![Multiple Airlines logo]()
$673
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 September 17, 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 September 17, 2026.
This Turkish Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Wed 1/2711:45 am -
1 stop14h 20m
Wed 2/311:05 am -
1 stop29h 55m
Deal found 9/13![Turkish Airlines logo]()
$749
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.
Fri 10/1611:15 am -
3 stops25h 50m
Fri 10/238:40 am -
2 stops18h 15m
Deal found 9/16![Multiple Airlines logo]()
$769
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.
Thu 11/269:35 pm -
Nonstop8h 40m
Wed 12/1611:20 am -
1 stop15h 45m
Deal found 9/17![United Airlines logo]()
$774
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 pm -
2 stops33h 35m
Sun 11/1512:35 pm -
2 stops35h 10m
Deal found 9/16![Scandinavian Airlines logo]()
$776
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 1/256:25 pm -
1 stop12h 30m
Wed 2/31:00 pm -
1 stop32h 25m
Deal found 9/13![Delta logo]()
$784
This Lufthansa deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Thu 10/153:35 pm -
1 stop10h 35m
Wed 1/132:45 pm -
1 stop12h 20m
Deal found 9/12![Lufthansa logo]()
$786
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.
Wed 10/282:21 pm -
2 stops20h 04m
Mon 11/97:20 am -
1 stop13h 40m
Deal found 9/16![Austrian Airlines logo]()
$825
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:49 pm -
1 stop13h 36m
Fri 10/2311:40 am -
1 stop17h 53m
Deal found 9/16![KLM logo]()
$1,496
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:35 pm -
Nonstop8h 40m
Mon 11/93:10 pm -
1 stop32h 05m
Deal found 9/16![Multiple Airlines logo]()
$769
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:15 pm -
2 stops34h 35m
Wed 11/41:00 pm -
2 stops34h 45m
Deal found 9/16![Scandinavian Airlines logo]()
$780
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 1/256:25 pm -
1 stop12h 30m
Tue 2/210:55 am -
1 stop34h 30m
Deal found 9/13![Delta logo]()
$784
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.
Sun 11/85:50 pm -
1 stop11h 30m
Sun 11/156:25 am -
1 stop11h 40m
Deal found 9/16![United Airlines logo]()
$786
This United deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:00 pm -
1 stop11h 20m
Tue 11/106:25 am -
1 stop13h 45m
Deal found 9/13![Multiple Airlines logo]()
$780
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.
Wed 11/116:00 am -
2 stops18h 30m
Sun 11/1512:55 pm -
1 stop32h 57m
Deal found 9/15![United Airlines logo]()
$789
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/242:44 pm -
2 stops16h 11m
Fri 11/276:30 am -
2 stops16h 48m
Deal found 9/13![Delta logo]()
$803
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:15 pm -
2 stops32h 15m
Tue 10/208:40 pm -
2 stops26h 30m
Deal found 9/16![Scandinavian Airlines logo]()
$824
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.
Sun 11/155:50 pm -
1 stop11h 30m
Thu 11/196:25 am -
1 stop11h 40m
Deal found 9/16![United Airlines logo]()
$791
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 10/259:05 pm -
1 stop30h 50m
Tue 11/108:05 pm -
2 stops25h 20m
Deal found 9/15![Multiple Airlines logo]()
$794
This Scandinavian Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/298:15 pm -
2 stops17h 40m
Wed 1/61:00 pm -
2 stops34h 45m
Deal found 9/14![Scandinavian Airlines logo]()
$829
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.
Wed 10/141:55 pm -
2 stops14h 25m
Wed 10/216:40 am -
1 stop14h 50m
Deal found 9/17![Delta logo]()
$864
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.
Tue 12/86:15 pm -
2 stops15h 40m
Wed 12/166:25 am -
2 stops15h 27m
Deal found 9/16![United Airlines logo]()
$800
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.
Wed 10/216:10 am -
2 stops21h 20m
Thu 10/291:00 pm -
2 stops34h 45m
Deal found 9/15![Scandinavian Airlines logo]()
$830
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:35 pm -
Nonstop8h 40m
Wed 11/1811:20 am -
1 stop15h 45m
Deal found 9/15![Multiple Airlines logo]()
$849
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/261:27 pm -
2 stops14h 28m
Tue 11/312:00 pm -
2 stops17h 33m
Deal found 9/13![Delta logo]()
$866
This United deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/159:35 pm -
Nonstop8h 40m
Mon 11/303:10 pm -
1 stop32h 05m
Deal found 9/12![Multiple Airlines logo]()
$851
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 12/31:02 pm -
2 stops15h 43m
Sat 12/1212:55 pm -
1 stop17h 00m
Deal found 9/15![Delta logo]()
$886
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 2/145:40 pm -
1 stop12h 45m
Mon 2/227:55 am -
2 stops18h 20m
Deal found 9/12![Multiple Airlines logo]()
$858
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 11/51:27 pm -
2 stops14h 48m
Fri 11/136:30 am -
2 stops18h 34m
Deal found 9/15![Delta logo]()
$933
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 1/107:15 pm -
1 stop11h 50m
Sun 1/179:30 am -
1 stop14h 15m
Deal found 9/12![Multiple Airlines logo]()
$867
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 10/207:15 pm -
1 stop19h 05m
Tue 10/2710:25 am -
1 stop13h 20m
Deal found 9/16![Multiple Airlines logo]()
$871
Last-minute flights from Chicago to MilanDiscover last-minute flight deals from Chicago to Milan. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Milan. Data last updated September 17, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Tue 10/63:45 pm -
1 stop11h 55m
Thu 10/2211:20 am -
1 stop14h 55m
Deal found 9/14![Aer Lingus logo]()
$680
This Gotogate deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Tue 10/1311:25 am -
1 stop14h 20m
Tue 10/272:35 pm -
1 stop26h 25m
Deal found 9/14![Turkish Airlines logo]()
$674
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
2 stops18h 10m
Wed 10/216:45 am -
2 stops20h 03m
Deal found 9/14![Multiple Airlines logo]()
$661
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:10 pm -
1 stop20h 40m
Wed 10/282:35 pm -
1 stop26h 25m
Deal found 9/16![Turkish Airlines logo]()
$678
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/197:25 pm -
2 stops19h 25m
Wed 10/288:55 am -
2 stops15h 25m
Deal found 9/14![Multiple Airlines logo]()
$613
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Mon 10/193:45 pm -
1 stop11h 55m
Wed 10/2811:45 am -
1 stop13h 35m
Deal found 9/14![Aer Lingus logo]()
$665
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/197:25 pm -
2 stops35h 35m
Wed 10/287:20 am -
1 stop17h 00m
Deal found 9/14![Multiple Airlines logo]()
$669
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.
Tue 10/2011:05 am -
2 stops23h 35m
Tue 10/272:45 pm -
2 stops34h 40m
Deal found 9/16![Multiple Airlines logo]()
$678
This Mytrip deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/254:55 pm -
3 stops34h 25m
Tue 11/106:40 am -
2 stops18h 40m
Deal found 9/13![Multiple Airlines logo]()
$664
This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/254:55 pm -
1 stop12h 10m
Tue 11/1011:45 am -
1 stop13h 35m
Deal found 9/13![Aer Lingus logo]()
$664
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/269:05 pm -
1 stop19h 55m
Tue 11/310:20 am -
1 stop15h 00m
Deal found 9/13![Multiple Airlines logo]()
$673
This Mytrip deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:30 pm -
2 stops23h 15m
Wed 11/46:00 am -
2 stops18h 20m
Deal found 9/13![Multiple Airlines logo]()
$588
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 September 17, 2026.
Search for one-way flight options from Chicago to Milan. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
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 10/137:25 pm -
2 stops31h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/133:20 pm -
2 stops24h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$282
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.
Fri 12/46:30 pm -
2 stops23h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$286
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.
Fri 12/46:30 pm -
2 stops31h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$287
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 1/146:30 pm -
2 stops32h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$306
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.
Fri 12/46:30 pm -
2 stops14h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 9/263:50 pm -
2 stops58h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$311
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 1/146:30 pm -
2 stops17h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 1/106:30 pm -
3 stops19h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/57:25 pm -
3 stops35h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 9/287:25 pm -
2 stops32h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 9/287:25 pm -
2 stops21h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$317
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 September 17, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $588 (Mytrip) |
One-way from | $282 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $1,015 |
Good round-trip deal | $917 or less |
Good one-way deal | $887 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 September 17, 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
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Thu 1/14
6:30 pm-9:50 am
2 stops32h 20m
Bergamo Orio Al Serio
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$306
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Wed 9/30
7:25 pm-11:40 pm
2 stops21h 15m
Bergamo Orio Al Serio
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$321
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Mon 10/5
7:25 pm-8:55 am
2 stops30h 30m
Bergamo Orio Al Serio
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$322
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Thu 1/14
6:30 pm-4:10 pm
2 stops14h 40m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$326
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Mon 1/11
6:30 pm-5:20 pm
2 stops15h 50m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$330
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Thu 1/14
6:30 pm-9:30 pm
3 stops20h 00m
Milan Malpensa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$339
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Wed 12/9
6:30 pm-10:50 am
2 stops33h 20m
Bergamo Orio Al Serio
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$350
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Sun 10/4
7:25 pm-11:55 pm
3 stops21h 30m
Bergamo Orio Al Serio
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$374
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Sat 11/21
5:20 pm-9:30 am
2 stops33h 10m
Bergamo Orio Al Serio
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$377
ChicagoMilan
MDW Chicago Midway - MXP Milan Malpensa
MDWMXP
Chicago Midway
Wed 10/14
3:20 pm-10:10 pm
2 stops23h 50m
Milan Malpensa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$392
Showing 1-10 of 60 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 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 | |
| Price Accuracy3 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-BGY
ORD-MXP
ORD-LIN
MDW-MXP
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-BGY
ORD-MXP
ORD-LIN
MDW-MXP
What is the cheapest month to book a flight from Chicago to Milan?
Currently, January is the cheapest month in which you can book a flight from Chicago to Milan (average of $587). Flying from Chicago to Milan in June is currently the most expensive (average of $1,383). 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 September 17, 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 September 17, 2026.
The most flights from CHI to MIL are scheduled on a Monday (5 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Chicago to Milan?
Airfare is below average for this route at the moment.
Chicago to Milan flights typically cost between $750 and $1,316 in October.The cheapest round-trip price found within the last 5 days was $588 on Multiple Airlines (Oct 28-Nov 4).
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 67% 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.
Copenhagen (CPH) is the most affordable 1-stop option, with an average round-trip price of $617.
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 6 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 September 17, 2026.
Read through reviews of airlines operating flights from Chicago to Milan, such as Scandinavian Airlines,United Airlines, andAer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Entertainment
6.8
Overall
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Entertainment
6.8
Overall
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Entertainment
6.8
Overall
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Entertainment
6.8
Overall
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Entertainment
6.8
Overall
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Comfort
7.4
Crew
8.1
Entertainment
6.8
Overall
7.4
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 5 airlines flying from Chicago to Milan
Discover the top 5 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 September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$401 | Average$653 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$445 | Average$646 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$627 | Average$828 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$780 | Average$1,236 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$823 | Average$1,227 | FlexibilityNo cancel fee | On-time76% |