Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Milan from $298

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Milan departing on 3/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Milan that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Milan.

Cheap last minute flights

Planning a quick getaway from Chicago to Milan? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Milan, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Milan

Find recent round-trip train or bus tickets from Chicago to Milan.

All round-trip flight deals to Milan

The cheapest plane tickets to Milan found on KAYAK recently.
8:25 pm - 11:35 pmORD-MXP
20h 10m1 stop
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
$403TAP AIR PORTUGAL
Find Deal
Sun, Jan 19 - Sun, Jan 26
8:25 pm - 4:55 pmORD-MXP
13h 30m1 stop
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
$405TAP AIR PORTUGAL
Find Deal
Sun, Jan 19 - Sun, Jan 26
7:15 pm - 11:05 amORD-MXP
32h 50m1 stop
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
$409TAP AIR PORTUGAL
Find Deal
Wed, Jan 22 - Wed, Jan 29
7:10 pm - 7:10 pmORD-MXP
17h 00m1 stop
8:00 pm - 3:50 pmMXP-ORD
26h 50m1 stop
$423Scandinavian Airlines
Find Deal
Sun, Jan 12 - Sun, Jan 26
7:10 pm - 7:10 pmORD-MXP
17h 00m1 stop
8:00 pm - 3:50 pmMXP-ORD
26h 50m1 stop
$425Scandinavian Airlines
Find Deal
Sun, Jan 12 - Sun, Jan 26
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$570Aer Lingus
Find Deal
Wed, Dec 4 - Thu, Dec 12
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$575Aer Lingus
Find Deal
Wed, Dec 4 - Fri, Dec 13
6:35 pm - 1:15 pmORD-LIN
11h 40m1 stop
7:25 am - 7:20 pmLIN-ORD
18h 55m2 stops
$632British Airways
Find Deal
Mon, Jan 27 - Fri, Feb 7
5:00 pm - 1:15 pmORD-LIN
13h 15m1 stop
7:25 am - 1:55 pmLIN-ORD
13h 30m1 stop
$645British Airways
Find Deal
Sun, Jan 26 - Fri, Feb 14
12:30 pm - 4:10 pmORD-LIN
20h 40m2 stops
11:00 am - 9:28 pmLIN-ORD
41h 28m2 stops
$827ITA Airways
Find Deal
Tue, Feb 4 - Tue, Feb 18
1:16 pm - 7:00 pmMDW-MXP
22h 44m3 stops
Wed, Mar 5
12:26 pm - 11:10 pmMDW-MXP
27h 44m2 stops
Fri, Feb 21
7:15 pm - 2:45 pmORD-MXP
12h 30m1 stop
$360Scandinavian Airlines
Find Deal
Sun, Mar 30
7:10 pm - 7:10 pmORD-MXP
17h 00m1 stop
$362Scandinavian Airlines
Find Deal
Sun, Jan 19
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
$471Aer Lingus
Find Deal
Mon, Mar 31
7:15 pm - 4:55 pmORD-MXP
14h 40m1 stop
$486TAP AIR PORTUGAL
Find Deal
Wed, Jan 1
7:40 pm - 11:05 amORD-LIN
32h 25m1 stop
$597Aer Lingus
Find Deal
Wed, Jan 1
4:45 pm - 7:30 pmORD-MXP
19h 45m3 stops
$699TAP AIR PORTUGAL
Find Deal
Tue, Apr 1
8:00 pm - 10:20 amORD-MXP
31h 20m2 stops
$897United Airlines
Find Deal
Sun, Dec 22
8:25 pm - 2:20 pmORD-LIN
34h 55m2 stops
$917United Airlines
Find Deal
Sun, Dec 22
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$580Aer Lingus
Find Deal
Sun, Nov 24 - Wed, Dec 4
9:50 am - 7:55 pmORD-BGY
27h 05m3 stops
8:35 pm - 4:15 pmBGY-ORD
26h 40m2 stops
Sun, Nov 24 - Tue, Dec 3
3:26 pm - 10:20 amORD-MXP
35h 54m3 stops
3:15 pm - 4:06 pmMXP-ORD
31h 51m3 stops
Sun, Nov 24 - Wed, Dec 4
7:10 pm - 10:30 amORD-MXP
32h 20m1 stop
8:00 pm - 3:50 pmMXP-ORD
26h 50m1 stop
$731Scandinavian Airlines
Find Deal
Sun, Nov 24 - Wed, Dec 4
8:25 pm - 11:35 pmORD-MXP
20h 10m1 stop
5:45 pm - 3:30 pmMXP-ORD
28h 45m1 stop
$872TAP AIR PORTUGAL
Find Deal
Sun, Nov 24 - Tue, Dec 3
7:10 pm - 10:30 amORD-MXP
32h 20m1 stop
8:00 pm - 3:50 pmMXP-ORD
26h 50m1 stop
$1,453Scandinavian Airlines
Find Deal
Sun, Nov 24 - Sun, Dec 1
4:39 pm - 4:55 pmORD-MXP
41h 16m2 stops
12:00 pm - 8:07 pmMXP-ORD
39h 07m2 stops
$1,944TAP AIR PORTUGAL
Find Deal
Sat, Nov 23 - Mon, Dec 2
9:30 pm - 12:50 pmORD-MXP
8h 20mnonstop
3:05 pm - 6:10 pmMXP-ORD
10h 05mnonstop
$2,167United Airlines
Find Deal
Sun, Nov 24 - Tue, Dec 3
9:10 pm - 7:30 amORD-MXP
27h 20m2 stops
9:15 am - 8:05 pmMXP-ORD
17h 50m2 stops
$2,179United Airlines
Find Deal
Sat, Nov 23 - Mon, Dec 2
1:50 pm - 2:10 pmORD-LIN
17h 20m2 stops
4:00 pm - 9:36 pmLIN-ORD
36h 36m2 stops
$3,681ITA Airways
Find Deal
Sat, Nov 23 - Sun, Dec 1
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,342United Airlines
Find Deal
Wed, Apr 9 - Wed, Apr 30
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,402United Airlines
Find Deal
Mon, Apr 28 - Mon, May 12
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,427United Airlines
Find Deal
Wed, Apr 23 - Sat, May 10
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,487United Airlines
Find Deal
Sat, Apr 26 - Sat, May 10
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,512United Airlines
Find Deal
Sat, May 10 - Wed, May 21
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
$1,517United Airlines
Find Deal
Sun, Apr 27 - Sun, May 25
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,612United Airlines
Find Deal
Wed, Apr 23 - Tue, Apr 29
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
$1,622United Airlines
Find Deal
Wed, May 14 - Mon, May 26
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
$1,692United Airlines
Find Deal
Fri, May 16 - Sun, May 25
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,707United Airlines
Find Deal
Wed, May 14 - Tue, May 20

TAP AIR PORTUGAL flights from Chicago to Milan

Our best TAP AIR PORTUGAL deals on Chicago to Milan flight tickets
TAP AIR PORTUGAL
Jan 19
ORD8:25 pmChicago O'Hare Intl
20h 10m
1 stop
MXP11:35 pmMilan Malpensa
Jan 26
MXP6:20 amMilan Malpensa
16h 10m
1 stop
ORD3:30 pmChicago O'Hare Intl
TAP AIR PORTUGAL
Jan 19
ORD8:25 pmChicago O'Hare Intl
13h 30m
1 stop
MXP4:55 pmMilan Malpensa
Jan 26
MXP6:20 amMilan Malpensa
16h 10m
1 stop
ORD3:30 pmChicago O'Hare Intl
TAP AIR PORTUGAL
Jan 22
ORD7:15 pmChicago O'Hare Intl
32h 50m
1 stop
MXP11:05 amMilan Malpensa
Jan 29
MXP6:20 amMilan Malpensa
16h 10m
1 stop
ORD3:30 pmChicago O'Hare Intl

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets
Turkish Airlines
Jan 19
ORD8:30 pmChicago O'Hare Intl
34h 05m
1 stop
MXP1:35 pmMilan Malpensa
Jan 27
MXP7:00 amMilan Malpensa
34h 10m
1 stop
ORD10:10 amChicago O'Hare Intl
Turkish Airlines
Jan 26
ORD8:30 pmChicago O'Hare Intl
18h 15m
1 stop
MXP9:45 pmMilan Malpensa
Feb 14
MXP7:00 amMilan Malpensa
18h 35m
1 stop
ORD6:35 pmChicago O'Hare Intl
Turkish Airlines
Apr 20
ORD11:35 amChicago O'Hare Intl
14h 10m
1 stop
MXP8:45 amMilan Malpensa
May 8
MXP8:10 pmMilan Malpensa
20h 40m
1 stop
ORD9:50 amChicago O'Hare Intl

See travel insights to Milan from

How to get the cheapest flight ticket from Chicago to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Chicago to Milan?

February. The cheapest time of year to fly to Milan from Chicago is February. Most expensive is June

What is the cheapest day to depart Chicago for Milan?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Friday

When is the cheapest time to fly from Chicago to Milan?

In the morning. Chicago to Milan flights are approximately 26% more expensive in the evening than in the morning

What is the cheapest Chicago to Milan flight route?

Chicago O'Hare Intl - Milan Malpensa. Fly from Chicago O'Hare Intl to Milan Malpensa for the best Chicago - Milan flight prices

How far in advance should you book Chicago to Milan flights?

47 days before. The cheapest time to buy a flight from Chicago to Milan is approximately 47 days to departure

Can stopping save me money on Chicago to Milan flights?

You could potentially save up to 82% on your flight if you consider stops on a Chicago to Milan flight.

How have Chicago to Milan flight prices changed over time?

As of November 2024, prices for Chicago to Milan flights are approximately 4% cheaper when compared to flights at the same time last year.

What is the typical price of a round-trip flight between Chicago and Milan?


When to book flights from Chicago to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Milan according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Milan (CHI to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Milan

Best Price Found

$298

Fastest flight time

8h 00m

Direct flights

Every day

Airports in Milan

3 airports
The best one-way flight to Milan from Chicago in the past 72 hours is $298. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $403.
The fastest flight from Chicago to Milan takes 8h 00m
Direct flights go from Chicago to Milan every day.
There are 3 airports near Milan: Milan Linate (LIN), Milan Malpensa (MXP), Bergamo Orio Al Serio (BGY)

  • How far is Chicago to Milan by plane?

    There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 11h 05m.

  • When did momondo last update prices for flights from Chicago to Milan?

    Prices for flights from Chicago to Milan are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Milan?

  • How old do you have to be to fly from Chicago to Milan?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Milan.

  • What documentation or ID do you need to fly to Milan?

    The required travel and health documents for your Milan trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milan. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Milan?

  • What is the most popular airline from Chicago to Milan?


Best airlines flying from Chicago to Milan

Compare and see reviews for airlines that fly from Chicago to Milan with momondo
Airline
Rating
Free Cancellation
Price
Scandinavian AirlinesPriceFrom $449Free CancellationRating
7.3
1,301 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $454Free CancellationRating
7.1
1,892 reviews
Search TAP AIR PORTUGAL flights
Aer LingusPriceFrom $509Free CancellationRating
7.1
1,089 reviews
Search Aer Lingus flights
American AirlinesPriceFrom $527Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
British AirwaysPriceFrom $532Free CancellationRating
6.6
6,837 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $562Free CancellationRating
7.4
3,915 reviews
Search Turkish Airlines flights
IcelandairPriceFrom $597Free CancellationRating
7.2
555 reviews
Search Icelandair flights
LufthansaPriceFrom $640Free CancellationRating
6.8
7,148 reviews
Search Lufthansa flights
ITA AirwaysPriceFrom $715Free CancellationRating
6.6
896 reviews
Search ITA Airways flights
United AirlinesPriceFrom $775Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
  • SWISS Flights From Chicago to Milan

    SWISS operates around 6 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,253, but momondo users have found SWISS deals from Chicago to Milan from as low as $1,014 round-trip. SWISS has been scored 7.6/10 in 1,637 reviews.

  • United Airlines Flights From Chicago to Milan

    United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago to Milan start from as low as $775 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $1,480. United Airlines operates 6 flights to Milan from Chicago in an average week. Users have rated it 7.4/10 across 9,171 reviews.


Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Milan from Chicago.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Milan.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Milan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


An easier way to manage your Milan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 11/25
Mon 12/2
Email me momondo's favorite deals

Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan