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Cheap flights from Chicago to Italy from $249

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 Italy departing on 9/11. 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
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Mon 5/13
Mon 5/20

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Easily compare round-trip flights from Chicago to Italy

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Italy by changing tabs
TAP AIR PORTUGAL
Nov 1
ORD9:25 pmChicago O'Hare Intl
13h 30m
1 stop
MXP4:55 pmMilan Malpensa
Nov 16
MXP5:45 pmMilan Malpensa
28h 45m
1 stop
ORD3:30 pmChicago O'Hare Intl
Scandinavian Airlines
Oct 7
ORD7:45 pmChicago O'Hare Intl
32h 45m
1 stop
FLR11:30 amFlorence Peretola
Oct 21
FLR12:20 pmFlorence Peretola
12h 35m
1 stop
ORD5:55 pmChicago O'Hare Intl
Aer Lingus
Sep 15
ORD3:45 pmChicago O'Hare Intl
11h 55m
1 stop
LIN10:40 amMilan Linate
Sep 25
LIN11:20 amMilan Linate
14h 45m
1 stop
ORD7:05 pmChicago O'Hare Intl
Delta
Oct 30
MDW5:50 pmChicago Midway
16h 35m
2 stops
FCO4:25 pmRome Fiumicino
Nov 15
FCO6:20 amRome Fiumicino
18h 45m
2 stops
MDW6:05 pmChicago Midway
Air France
Nov 4
MDW5:50 pmChicago Midway
13h 50m
2 stops
FCO2:40 pmRome Fiumicino
Nov 13
FCO1:50 pmRome Fiumicino
35h 09m
1 stop
MDW5:59 pmChicago Midway
Turkish Airlines
Sep 18
ORD11:25 amChicago O'Hare Intl
23h 50m
1 stop
MXP6:15 pmMilan Malpensa
Sep 24
MXP3:10 pmMilan Malpensa
25h 30m
1 stop
ORD9:40 amChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Italy

If you're looking for one-way flights from Chicago to Italy, view some of our deals below provided by Scandinavian Airlines, United Airlines and WestJet
Multiple Airlines
Sep 11
MDW8:13 pmChicago Midway
36h 27m
2 stops
MXP3:40 pmMilan Malpensa
Scandinavian Airlines
Oct 2
ORD7:45 pmChicago O'Hare Intl
30h 50m
2 stops
FLR9:35 amFlorence Peretola
WestJet
Jul 14
ORD5:55 pmChicago O'Hare Intl
35h 45m
1 stop
FCO12:40 pmRome Fiumicino

Search last-minute flights to Italy from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Italy
Multiple Airlines
May 15
ORD11:14 amChicago O'Hare Intl
20h 26m
1 stop
FCO2:40 pmRome Fiumicino
May 29
FCO8:40 pmRome Fiumicino
43h 15m
2 stops
ORD8:55 amChicago O'Hare Intl
Scandinavian Airlines
May 13
ORD7:45 pmChicago O'Hare Intl
16h 30m
1 stop
MXP7:15 pmMilan Malpensa
May 21
MXP11:20 amMilan Malpensa
13h 35m
1 stop
ORD5:55 pmChicago O'Hare Intl
ITA Airways
May 14
ORD3:00 pmChicago O'Hare Intl
9h 20m
FCO7:20 amRome Fiumicino
May 19
FCO9:20 amRome Fiumicino
10h 50m
ORD1:10 pmChicago O'Hare Intl
United Airlines
May 13
ORD9:20 pmChicago O'Hare Intl
32h 45m
1 stop
FCO1:05 pmRome Fiumicino
May 24
FCO1:05 pmRome Fiumicino
25h 53m
1 stop
ORD7:58 amChicago O'Hare Intl
British Airways
May 15
ORD7:10 pmChicago O'Hare Intl
17h 55m
1 stop
FCO8:05 pmRome Fiumicino
May 22
FCO11:05 amRome Fiumicino
10h 25m
ORD2:30 pmChicago O'Hare Intl
Air Canada
May 13
ORD2:15 pmChicago O'Hare Intl
14h 00m
1 stop
FCO11:15 amRome Fiumicino
May 22
FCO1:05 pmRome Fiumicino
14h 11m
1 stop
ORD8:16 pmChicago O'Hare Intl

Best airlines flying from Chicago to Italy

Compare and see reviews for airlines that fly from Chicago to Italy with momondo
Airline
Rating
Free Cancellation
Price
Scandinavian AirlinesPriceFrom $403Free CancellationRating
7.4
1,430 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $425Free CancellationRating
7.1
2,155 reviews
Search TAP AIR PORTUGAL flights
SWISSPriceFrom $451Free CancellationRating
7.8
2,013 reviews
Search SWISS flights
LufthansaPriceFrom $460Free CancellationRating
7.0
7,691 reviews
Search Lufthansa flights
IcelandairPriceFrom $464Free CancellationRating
7.1
1,329 reviews
Search Icelandair flights
KLMPriceFrom $475Free CancellationRating
7.8
1,592 reviews
Search KLM flights
IberiaPriceFrom $484Free CancellationRating
7.1
2,745 reviews
Search Iberia flights
Aer LingusPriceFrom $496Free CancellationRating
7.2
1,338 reviews
Search Aer Lingus flights
British AirwaysPriceFrom $500Free CancellationRating
6.8
6,868 reviews
Search British Airways flights
American AirlinesPriceFrom $502Free CancellationRating
7.3
14,677 reviews
Search American Airlines flights

Delta flights from Chicago to Italy

Our best Delta deals on Chicago to Italy flight tickets
Delta
Oct 30
MDW5:50 pmChicago Midway
16h 35m
2 stops
FCO4:25 pmRome Fiumicino
Nov 15
FCO6:20 amRome Fiumicino
18h 45m
2 stops
MDW6:05 pmChicago Midway
Delta
Oct 30
MDW5:50 pmChicago Midway
16h 35m
2 stops
FCO4:25 pmRome Fiumicino
Nov 15
FCO6:20 amRome Fiumicino
18h 45m
2 stops
MDW6:05 pmChicago Midway
Delta
Nov 3
MDW6:15 pmChicago Midway
15h 10m
2 stops
FCO4:25 pmRome Fiumicino
Nov 14
FCO6:20 amRome Fiumicino
18h 45m
2 stops
MDW6:05 pmChicago Midway

Air France flights from Chicago to Italy

Our best Air France deals on Chicago to Italy flight tickets
Air France
Nov 4
MDW5:50 pmChicago Midway
13h 50m
2 stops
FCO2:40 pmRome Fiumicino
Nov 13
FCO1:50 pmRome Fiumicino
35h 09m
1 stop
MDW5:59 pmChicago Midway
Air France
Nov 4
MDW5:50 pmChicago Midway
13h 50m
2 stops
FCO2:40 pmRome Fiumicino
Nov 13
FCO6:20 amRome Fiumicino
18h 45m
2 stops
MDW6:05 pmChicago Midway
Air France
Nov 4
MDW5:50 pmChicago Midway
13h 50m
2 stops
FCO2:40 pmRome Fiumicino
Nov 13
FCO1:50 pmRome Fiumicino
35h 09m
1 stop
MDW5:59 pmChicago Midway

How to get the cheapest flight ticket from Chicago to Italy

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 airline that flies to Italy from Chicago?

Scandinavian Airlines. Aer Lingus, Air Serbia, and Icelandair are the most popular carriers operating from Chicago to Italy

What is the cheapest Chicago to Italy flight route?

Chicago O'Hare Intl - Rome Fiumicino. Fly from Chicago O'Hare Intl to Rome Fiumicino for the best Chicago - Italy flight prices

What cabin class options are available on Chicago to Italy flights?

There are 3 cabin classes available to choose from on Chicago to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Italy flights?

You could potentially save up to 16% on your flight if you consider stops on a Chicago to Italy flight.

Cheap Chicago to Italy flight deals and tips

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

Best Price Found

$249

Fastest flight time

8h 45m

Direct flights

Every day

Airports in Italy

6 airports
The best one-way flight to Italy from Chicago in the past 72 hours is $249. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $455.
The fastest flight from Chicago to Italy takes 8h 45m
Direct flights go from Chicago to Italy every day.
There are 6 airports near Italy: Milan Linate (LIN), Rome Fiumicino (FCO), Milan Malpensa (MXP), Venice Marco Polo (VCE), Naples (NAP), Florence Peretola (FLR)

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

    Prices for flights from Chicago to Italy refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Italy.

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

    The travel and health documents you'll need for your trip to Italy may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Italy. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.


Why use momondo?

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

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 Italy from Chicago.

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

All flight searches from Chicago to Italy on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Italy from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are not ready to book a flight from Chicago to Italy now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Italy and let you know when they change.


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Mon 5/13
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