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Cheap flights from Sicily to Chicago from $395

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sicily to Chicago departing on 9/30. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Sicily to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
ITA Airways Logo
6:10 am - 1:10 pm
PMO
-
ORD
14h 00m
1 stop
ITA Airways Logo
3:00 pm - 10:30 pm
ORD
-
PMO
24h 30m
1 stop
$620ITA Airways
Sun, Aug 23 - Tue, Sep 1
ITA Airways Logo
6:10 am - 1:10 pm
PMO
-
ORD
14h 00m
1 stop
ITA Airways Logo
3:00 pm - 10:30 pm
ORD
-
PMO
24h 30m
1 stop
$621ITA Airways
Sun, Aug 23 - Tue, Sep 1
ITA Airways Logo
6:00 am - 1:10 pm
CTA
-
ORD
14h 10m
1 stop
ITA Airways Logo
3:00 pm - 8:45 pm
ORD
-
CTA
22h 45m
1 stop
$622ITA Airways
Sun, Aug 23 - Tue, Sep 1
Finnair Logo
10:30 am - 5:50 pm
CTA
-
ORD
14h 20m
1 stop
Finnair Logo
9:30 pm - 5:55 pm
ORD
-
CTA
13h 25m
1 stop
$733Finnair
Tue, Aug 18 - Tue, Aug 25
Finnair Logo
10:30 am - 5:50 pm
CTA
-
ORD
14h 20m
1 stop
Finnair Logo
4:30 pm - 5:55 pm
ORD
-
CTA
18h 25m
2 stops
$737Finnair
Tue, Aug 18 - Tue, Aug 25
Multiple Airlines Logo
4:10 pm - 2:30 pm
PMO
-
ORD
29h 20m
1 stop
Multiple Airlines Logo
5:20 pm - 3:00 pm
ORD
-
PMO
14h 40m
2 stops
$753Multiple Airlines
Tue, Aug 4 - Wed, Aug 12
British Airways Logo
12:15 pm - 1:50 pm
PMO
-
ORD
32h 35m
1 stop
British Airways Logo
10:09 am - 11:10 am
ORD
-
PMO
18h 01m
2 stops
$760British Airways
Tue, Aug 4 - Wed, Aug 12
Delta Logo
3:45 pm - 4:17 pm
PMO
-
ORD
31h 32m
2 stops
Delta Logo
1:59 pm - 3:00 pm
ORD
-
PMO
18h 01m
2 stops
$774Delta
Tue, Aug 4 - Wed, Aug 12
Multiple Airlines Logo
6:10 am - 6:33 pm
PMO
-
MDW
19h 23m
2 stops
Multiple Airlines Logo
1:51 pm - 12:15 pm
MDW
-
PMO
15h 24m
2 stops
$1,001Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
Delta Logo
3:45 pm - 4:15 pm
PMO
-
MDW
31h 30m
2 stops
Delta Logo
9:24 am - 3:00 pm
MDW
-
PMO
22h 36m
2 stops
$1,698Delta
Sun, Aug 9 - Sun, Aug 23

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Finnair flights from Sicily to Chicago

Our best Finnair deals on Sicily to Chicago flight tickets
Finnair
Aug 18
CTA10:30 amCatania Fontanarossa
14h 20m
1 stop
ORD5:50 pmChicago O'Hare Intl
Aug 25
ORD9:30 pmChicago O'Hare Intl
13h 25m
1 stop
CTA5:55 pmCatania Fontanarossa
$733
Finnair
Aug 18
CTA10:30 amCatania Fontanarossa
14h 20m
1 stop
ORD5:50 pmChicago O'Hare Intl
Aug 25
ORD4:30 pmChicago O'Hare Intl
18h 25m
2 stops
CTA5:55 pmCatania Fontanarossa
$737

Lufthansa flights from Sicily to Chicago

Our best Lufthansa deals on Sicily to Chicago flight tickets
Lufthansa
Aug 31
PMO11:50 amPalermo Punta Raisi
15h 05m
2 stops
ORD7:55 pmChicago O'Hare Intl
Sep 17
ORD4:05 pmChicago O'Hare Intl
17h 50m
1 stop
PMO4:55 pmPalermo Punta Raisi
$787
Lufthansa
Aug 31
PMO11:50 amPalermo Punta Raisi
15h 05m
2 stops
ORD7:55 pmChicago O'Hare Intl
Sep 17
ORD4:05 pmChicago O'Hare Intl
17h 50m
1 stop
PMO4:55 pmPalermo Punta Raisi
$792
Lufthansa
Aug 31
PMO11:50 amPalermo Punta Raisi
15h 05m
2 stops
ORD7:55 pmChicago O'Hare Intl
Sep 17
ORD4:05 pmChicago O'Hare Intl
17h 50m
1 stop
PMO4:55 pmPalermo Punta Raisi
$793

momondo Fare Finder

 
Customize your flight search to find flights from Sicily 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, momondo users made 832,500 searches. Data last updated July 9, 2026.
Use the filters below to find and compare flights from Sicily to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Sun 8/23

6:10 am-1:10 pm

1 stop14h 00m

Chicago O'Hare Intl

Tue 9/1

3:00 pm-10:30 pm

1 stop24h 30m

$620

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Sun 8/23

6:10 am-1:10 pm

1 stop14h 00m

Chicago O'Hare Intl

Tue 9/1

3:00 pm-10:30 pm

1 stop24h 30m

$621

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Sun 8/23

6:00 am-1:10 pm

1 stop14h 10m

Chicago O'Hare Intl

Tue 9/1

3:00 pm-8:45 pm

1 stop22h 45m

$622
Quickest round-trip

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Tue 8/18

10:30 am-5:50 pm

1 stop14h 20m

Chicago O'Hare Intl

Tue 8/25

9:30 pm-5:55 pm

1 stop13h 25m

$733

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Tue 8/18

10:30 am-5:50 pm

1 stop14h 20m

Chicago O'Hare Intl

Tue 8/25

4:30 pm-5:55 pm

2 stops18h 25m

$737

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Tue 8/4

4:10 pm-2:30 pm

1 stop29h 20m

Chicago O'Hare Intl

Wed 8/12

5:20 pm-3:00 pm

2 stops14h 40m

$753

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Tue 8/4

12:15 pm-1:50 pm

1 stop32h 35m

Chicago O'Hare Intl

Wed 8/12

10:09 am-11:10 am

2 stops18h 01m

$760

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Tue 8/4

3:45 pm-4:17 pm

2 stops31h 32m

Chicago O'Hare Intl

Wed 8/12

1:59 pm-3:00 pm

2 stops18h 01m

$774

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Sat 8/8

6:10 am-6:33 pm

2 stops19h 23m

Chicago Midway

Sat 8/15

1:51 pm-12:15 pm

2 stops15h 24m

$1,001

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Sun 8/9

3:45 pm-4:15 pm

2 stops31h 30m

Chicago Midway

Sun 8/23

9:24 am-3:00 pm

2 stops22h 36m

$1,698

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Sicily to Chicago

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 from Sicily to Chicago?

British Airways, Turkish Airlines, and ITA Airways are the most popular carriers operating from Sicily to Chicago

Cheap Sicily to Chicago flight deals and tips

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

Fastest flight time

13h 55m

Direct flights

None
The fastest flight from Sicily to Chicago takes 13h 55m
There are no direct flights from Sicily to Chicago. There are no popular flight routes from Sicily to Chicago.
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Frequently asked questions about flying from Sicily to Chicago

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

    Prices for flights from Sicily to Chicago were last updated today.

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

    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 Sicily to Chicago.

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

    The required travel and health documents for your Chicago 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 Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Sicily to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo allows you to filter the results for Sicily to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Sicily.

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

Of course. momondo tracks the price of Sicily to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport