- Must visit
Pinacoteca di Brera
One of Italy’s leading art museums, known for masterpieces by Raphael, Caravaggio, and Mantegna in the elegant Brera district.
Flights from Chicago, IL to Milan depart on average 88 times per day, taking around 10h 13m. Cheap flight tickets for this journey start at $489 (€394) if you book in advance.
The earliest flight runs at 05:00, the last at 23:50. The fastest flight covers the 4531 miles (7293 km) distance in 11h 55m. August is the cheapest month to fly.
Distance 4531 miles (7293 km) |
Average flight duration 10h 13m |
Cheapest ticket price $489 (€394) |
Flights per day 88 |
Fastest flight 11h 55m |
First flight 5:00 AM |
Last flight 11:50 PM |
Cheapest Month Aug |
Cheapest Day Sun |
High Season Jul - Sep |
Low Season Oct - Dec |
Best time to book 42 days |
Cheapest price
$575
Average price
$676
Fastest journey
12 h 15 m
Average duration
21 h 17 m
Flights per day
3
Distance
7293 km
The best way to find a cheap flight ticket from Chicago, IL to Milan is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Milan will cost around $676 if you buy it on the day, but the cheapest tickets can be found for only $575.
Of the 3 flights that leave Chicago, IL for Milan onWed, Jun 03, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, Jun 03 the direct flights cover the 7293 km distance in an average of 21 h 17 m but if you time it right, some flights will get you there in just 12 h 15 m .
On Wed, Jun 03 the longest flights will take 1 d 5 h 50 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.






The table below shows live departures for Chicago, IL to Milan flights for today, Tuesday, June 2. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
UA1939 · UA19 | 5:00 AM O'Hare International Airport | 19h30 | 7:30 AM Milan Malpensa Airport | 1 transfer | |
UA2295 · UA19 | 6:00 AM O'Hare International Airport | 18h30 | 7:30 AM Milan Malpensa Airport | 1 transfer | |
KL6081+ KL7643 | 6:07 AM O'Hare International Airport | 17h38 | 6:45 AM Milan Malpensa Airport | 1 transfer | |
UA563 · UA19 | 7:10 AM O'Hare International Airport | 17h20 | 7:30 AM Milan Malpensa Airport | 1 transfer | |
UA2301 · UA19 | 8:45 AM O'Hare International Airport | 15h45 | 7:30 AM Milan Malpensa Airport | 1 transfer | |
B6312 · B6331 | 8:50 AM O'Hare International Airport | 16h20 | 8:10 AM Milan Malpensa Airport | 1 transfer | |
AF2712 · AF3672 | 9:49 AM O'Hare International Airport | 16h36 | 9:25 AM Milan Malpensa Airport | 1 transfer | |
KL5996+ KL6081 | 10:15 AM O'Hare International Airport | 13h30 | 6:45 AM Milan Malpensa Airport | 1 transfer | |
KL6085+ KL5996 | 10:15 AM O'Hare International Airport | 18h50 | 12:05 PM Milan Malpensa Airport | 1 transfer | |
AA198+ AA4356 | 10:40 AM O'Hare International Airport | 15h25 | 9:05 AM Milan Malpensa Airport | 1 transfer | |
UA1856 · UA19 | 10:51 AM O'Hare International Airport | 13h39 | 7:30 AM Milan Malpensa Airport | 1 transfer | |
TK186 · TK1875 | 11:25 AM O'Hare International Airport | 23h20 | 5:45 PM Milan Malpensa Airport | 1 transfer | |
TK186 · TK1873 | 11:25 AM O'Hare International Airport | 14h15 | 8:40 AM Milan Malpensa Airport | 1 transfer | |
TK186 · TK1877 | 11:25 AM O'Hare International Airport | 29h20 | 11:45 PM Milan Malpensa Airport | 1 transfer | |
TK186 · TK1895 | 11:25 AM O'Hare International Airport | 19h40 | 2:05 PM Milan Malpensa Airport | 1 transfer | |
KL6504 · KL6079 | 11:26 AM O'Hare International Airport | 14h59 | 9:25 AM Milan Malpensa Airport | 1 transfer | |
AF5700 · AF3672 | 11:26 AM O'Hare International Airport | 14h59 | 9:25 AM Milan Malpensa Airport | 1 transfer | |
AA1743 · AA298 | 12:00 PM O'Hare International Airport | 15h05 | 10:05 AM Milan Malpensa Airport | 1 transfer | |
UA606 · UA19 | 12:11 PM O'Hare International Airport | 12h19 | 7:30 AM Milan Malpensa Airport | 1 transfer | |
AA1349 · AA198 | 12:47 PM O'Hare International Airport | 13h18 | 9:05 AM Milan Malpensa Airport | 1 transfer | |
BA5224 · BA1582 | 12:47 PM O'Hare International Airport | 13h18 | 9:05 AM Milan Malpensa Airport | 1 transfer | |
AF3635+ AF6829 | 12:59 PM O'Hare International Airport | 16h06 | 12:05 PM Milan Malpensa Airport | 1 transfer | |
KL5995+ KL6085 | 12:59 PM O'Hare International Airport | 16h06 | 12:05 PM Milan Malpensa Airport | 1 transfer | |
UA1695 · UA19 | 1:00 PM O'Hare International Airport | 11h30 | 7:30 AM Milan Malpensa Airport | 1 transfer | |
AA1859 · AA298 | 1:35 PM O'Hare International Airport | 13h30 | 10:05 AM Milan Malpensa Airport | 1 transfer | |
UA3512 · UA8060 | 2:02 PM O'Hare International Airport | 13h18 | 10:20 AM Milan Malpensa Airport | 1 transfer | |
AA3148 · AA206 | 2:30 PM O'Hare International Airport | 14h00 | 11:30 AM Milan Malpensa Airport | 1 transfer | |
LX7 · LX1612 | 2:40 PM O'Hare International Airport | 12h10 | 9:50 AM Milan Malpensa Airport | 1 transfer | |
LH9153+ LH248 | 3:10 PM O'Hare International Airport | 12h25 | 10:35 AM Milan Malpensa Airport | 1 transfer | |
UA944 · UA9540 | 3:10 PM O'Hare International Airport | 16h30 | 2:40 PM Milan Linate Airport | 1 transfer | |
UA944 · UA8768 | 3:10 PM O'Hare International Airport | 13h50 | 12:00 PM Milan Linate Airport | 1 transfer | |
UA944 · UA9382 | 3:10 PM O'Hare International Airport | 19h20 | 5:30 PM Milan Linate Airport | 1 transfer | |
LH9153+ LH270 | 3:10 PM O'Hare International Airport | 11h50 | 10:00 AM Milan Linate Airport | 1 transfer | |
UA944 · UA9090 | 3:10 PM O'Hare International Airport | 20h30 | 6:40 PM Milan Malpensa Airport | 1 transfer | |
UA944 · UA9140 | 3:10 PM O'Hare International Airport | 12h25 | 10:35 AM Milan Malpensa Airport | 1 transfer | |
UA944 · UA9220 | 3:10 PM O'Hare International Airport | 19h50 | 6:00 PM Milan Malpensa Airport | 1 transfer | |
UA944 · UA9372 | 3:10 PM O'Hare International Airport | 11h50 | 10:00 AM Milan Linate Airport | 1 transfer | |
AA2925 · AA298 | 3:16 PM O'Hare International Airport | 11h49 | 10:05 AM Milan Malpensa Airport | 1 transfer | |
BA5686 · BA1624 | 3:16 PM O'Hare International Airport | 11h49 | 10:05 AM Milan Malpensa Airport | 1 transfer | |
LH437+ LH1850 | 3:35 PM O'Hare International Airport | 10h35 | 9:10 AM Milan Linate Airport | 1 transfer | |
LH437+ LH5188 | 3:35 PM O'Hare International Airport | 12h05 | 10:40 AM Milan Linate Airport | 1 transfer | |
UA8458 · UA8060 | 3:40 PM O'Hare International Airport | 11h40 | 10:20 AM Milan Malpensa Airport | 1 transfer | |
AA8104 · AA7994 | 3:45 PM O'Hare International Airport | 11h55 | 10:40 AM Milan Linate Airport | 1 transfer | |
EI122 · EI432 | 3:45 PM O'Hare International Airport | 11h55 | 10:40 AM Milan Linate Airport | 1 transfer | |
LX3205+ LX1612 | 3:55 PM O'Hare International Airport | 10h55 | 9:50 AM Milan Malpensa Airport | 1 transfer | |
LH431 · LH272 | 4:05 PM O'Hare International Airport | 12h55 | 12:00 PM Milan Linate Airport | 1 transfer | |
LH431 · LH248 | 4:05 PM O'Hare International Airport | 11h30 | 10:35 AM Milan Malpensa Airport | 1 transfer | |
UA8837 · UA9372 | 4:05 PM O'Hare International Airport | 10h55 | 10:00 AM Milan Linate Airport | 1 transfer | |
LH431 · LH270 | 4:05 PM O'Hare International Airport | 10h55 | 10:00 AM Milan Linate Airport | 1 transfer | |
UA8837 · UA9140 | 4:05 PM O'Hare International Airport | 11h30 | 10:35 AM Milan Malpensa Airport | 1 transfer | |
IB673 · BA4272 | 4:55 PM O'Hare International Airport | 13h45 | 1:40 PM Milan Malpensa Airport | 1 transfer | |
AA8754 · AA8668 | 4:55 PM O'Hare International Airport | 13h45 | 1:40 PM Milan Malpensa Airport | 1 transfer | |
BA294 · BA572 | 5:00 PM O'Hare International Airport | 13h30 | 1:30 PM Milan Linate Airport | 1 transfer | |
BA294 · BA584 | 5:00 PM O'Hare International Airport | 13h25 | 1:25 PM Milan Malpensa Airport | 1 transfer | |
AA7003 · AA6831 | 5:00 PM O'Hare International Airport | 13h30 | 1:30 PM Milan Linate Airport | 1 transfer | |
AA7003 · AA7149 | 5:00 PM O'Hare International Airport | 17h15 | 5:15 PM Milan Linate Airport | 1 transfer | |
AA7003 · AA6833 | 5:00 PM O'Hare International Airport | 12h30 | 12:30 PM Milan Linate Airport | 1 transfer | |
BA294 · BA570 | 5:00 PM O'Hare International Airport | 12h30 | 12:30 PM Milan Linate Airport | 1 transfer | |
LO2098 · LO3920 · LO319 | 5:10 PM O'Hare International Airport | 18h45 | 6:55 PM Milan Malpensa Airport | 2 transfers | |
LO2098 · LO3910 · LO317 | 5:10 PM O'Hare International Airport | 33h35 | 9:45 AM Milan Malpensa Airport | 2 transfers | |
LO2098 · LO3908 · LO319 | 5:10 PM O'Hare International Airport | 18h45 | 6:55 PM Milan Malpensa Airport | 2 transfers | |
LO2098 · LO3920 · LO317 | 5:10 PM O'Hare International Airport | 33h35 | 9:45 AM Milan Malpensa Airport | 2 transfers | |
AF137 · AF1230 | 5:10 PM O'Hare International Airport | 14h35 | 2:45 PM Milan Malpensa Airport | 1 transfer | |
LO2098 · LO3908 · LO317 | 5:10 PM O'Hare International Airport | 33h35 | 9:45 AM Milan Malpensa Airport | 2 transfers | |
LO2098 · LO3924 · LO317 | 5:10 PM O'Hare International Airport | 33h35 | 9:45 AM Milan Malpensa Airport | 2 transfers | |
AF137 · AF1730 | 5:10 PM O'Hare International Airport | 17h25 | 5:35 PM Milan Malpensa Airport | 1 transfer | |
LO2098 · LO3906 · LO319 | 5:10 PM O'Hare International Airport | 18h45 | 6:55 PM Milan Malpensa Airport | 2 transfers | |
LO2098 · LO3906 · LO317 | 5:10 PM O'Hare International Airport | 33h35 | 9:45 AM Milan Malpensa Airport | 2 transfers | |
SN8804+ SN3147 | 6:00 PM O'Hare International Airport | 11h20 | 12:20 PM Milan Linate Airport | 1 transfer | |
UA953 · UA9380 | 6:00 PM O'Hare International Airport | 15h40 | 4:40 PM Milan Malpensa Airport | 1 transfer | |
UA972 · UA9947 | 6:00 PM O'Hare International Airport | 11h20 | 12:20 PM Milan Linate Airport | 1 transfer | |
LH9269+ LH1852 | 6:00 PM O'Hare International Airport | 12h00 | 1:00 PM Milan Linate Airport | 1 transfer | |
LH9269+ LH9448 | 6:00 PM O'Hare International Airport | 11h15 | 12:15 PM Milan Malpensa Airport | 1 transfer | |
UA907 · UA9220 | 6:30 PM O'Hare International Airport | 16h30 | 6:00 PM Milan Malpensa Airport | 1 transfer | |
UA907 · UA9384 | 6:30 PM O'Hare International Airport | 16h55 | 6:25 PM Milan Linate Airport | 1 transfer | |
UA907 · UA9090 | 6:30 PM O'Hare International Airport | 17h10 | 6:40 PM Milan Malpensa Airport | 1 transfer | |
UA907 · UA9540 | 6:30 PM O'Hare International Airport | 13h10 | 2:40 PM Milan Linate Airport | 1 transfer | |
LH9151+ LH5636 | 6:30 PM O'Hare International Airport | 12h20 | 1:50 PM Milan Malpensa Airport | 1 transfer | |
UA907 · UA9382 | 6:30 PM O'Hare International Airport | 16h00 | 5:30 PM Milan Linate Airport | 1 transfer | |
AA7018 · AA6783 | 7:05 PM O'Hare International Airport | 12h55 | 3:00 PM Milan Linate Airport | 1 transfer | |
AA7018 · AA7149 | 7:05 PM O'Hare International Airport | 15h10 | 5:15 PM Milan Linate Airport | 1 transfer | |
BA298 · BA572 | 7:05 PM O'Hare International Airport | 11h25 | 1:30 PM Milan Linate Airport | 1 transfer | |
BA298 · BA574 | 7:05 PM O'Hare International Airport | 12h55 | 3:00 PM Milan Linate Airport | 1 transfer | |
AA7018 · AA6831 | 7:05 PM O'Hare International Airport | 11h25 | 1:30 PM Milan Linate Airport | 1 transfer | |
LX9+ LX1628 | 7:05 PM O'Hare International Airport | 11h55 | 2:00 PM Milan Malpensa Airport | 1 transfer | |
SK944 · SK1683 | 7:15 PM O'Hare International Airport | 12h50 | 3:05 PM Milan Malpensa Airport | 1 transfer | |
| Wednesday, June 3 | |||||
![]() | 12:50 AM Chicago, IL | 29h50 | 6:40 AM Milan | 0 transfersDirect | |
| Tuesday, June 2 | |||||
TK6 · TK1873 | 8:10 PM O'Hare International Airport | 29h30 | 8:40 AM Milan Malpensa Airport | 1 transfer | |
TK6 · TK1875 | 8:10 PM O'Hare International Airport | 14h35 | 5:45 PM Milan Malpensa Airport | 1 transfer | |
TK6 · TK1877 | 8:10 PM O'Hare International Airport | 20h35 | 11:45 PM Milan Malpensa Airport | 1 transfer | |
TK6 · TK1895 | 8:10 PM O'Hare International Airport | 34h05 | 1:15 PM Milan Malpensa Airport | 1 transfer | |
AF139 · AF1230 | 8:15 PM O'Hare International Airport | 11h30 | 2:45 PM Milan Malpensa Airport | 1 transfer | |
AF139 · AF1130 | 8:15 PM O'Hare International Airport | 19h45 | 11:00 PM Milan Malpensa Airport | 1 transfer | |
AF139 · AF1730 | 8:15 PM O'Hare International Airport | 14h20 | 5:35 PM Milan Malpensa Airport | 1 transfer | |
BA1518+ BA586 | 8:50 PM O'Hare International Airport | 14h00 | 5:50 PM Milan Malpensa Airport | 1 transfer | |
AA54+ AA7149 | 8:50 PM O'Hare International Airport | 13h25 | 5:15 PM Milan Linate Airport | 1 transfer | |
AA54+ AA6839 | 8:50 PM O'Hare International Airport | 14h45 | 6:35 PM Milan Linate Airport | 1 transfer | |
BA1518+ BA576 | 8:50 PM O'Hare International Airport | 13h25 | 5:15 PM Milan Linate Airport | 1 transfer | |
AA54+ AA7188 | 8:50 PM O'Hare International Airport | 14h00 | 5:50 PM Milan Malpensa Airport | 1 transfer | |
BA296 · BA576 | 9:15 PM O'Hare International Airport | 13h00 | 5:15 PM Milan Linate Airport | 1 transfer | |
AA7005 · AA7149 | 9:15 PM O'Hare International Airport | 13h00 | 5:15 PM Milan Linate Airport | 1 transfer | |
BA296 · BA586 | 9:15 PM O'Hare International Airport | 13h35 | 5:50 PM Milan Malpensa Airport | 1 transfer | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Milan — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Milan trip today.
One of Italy’s leading art museums, known for masterpieces by Raphael, Caravaggio, and Mantegna in the elegant Brera district.
A major museum of 20th-century Italian art facing Piazza del Duomo, with strong Futurist holdings and striking city views.
A contemporary museum focused on world cultures and major temporary exhibitions, popular for its modern architecture and changing shows.
Milan’s canal district, best known for waterside walks, photogenic bridges, and lively atmosphere day and night.
A charming historic neighborhood of narrow streets, galleries, boutiques, and classic Milan character, ideal for wandering.
Milan’s main square and the symbolic heart of the city, surrounded by major landmarks and constant urban energy.
Creamy saffron risotto, one of Milan's signature dishes, prized for its rich flavor and golden color.
Braised veal shank cooked slowly until tender, traditionally served with gremolata and often paired with risotto.
Breaded veal cutlet fried in butter, a classic Milanese specialty and one of the city's most famous dishes.
Celebrated fine dining restaurant offering creative haute cuisine with an elegant, Michelin-starred reputation.
Famous central bakery known for panzerotti, a beloved casual stop near the Duomo with constant local appeal.
Modern Milanese restaurant known for refined Lombard classics in a stylish contemporary setting.
Milan is pricier than most Italian cities, especially for hotels, central dining, and aperitivo areas.
Service is often included or covered by coperto. Tipping is not required, but rounding up or leaving EUR 1-5 for good service is appreciated. Taxis can be rounded up.
Official public transport app
Milan Malpensa Airport -> Milano Centrale
Find answers to the most common questions about traveling from Chicago, IL to Milan by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Milan, this guide helps you travel smarter and with confidence.

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