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Deals on flights from Chicago to Italy*

Chicago (ORD)to

Rome (FCO)
20 Aug 2026 - 27 Aug 2026
From
$824.43
Seen: 21 hrs ago
Roundtrip*
Economy

Chicago (ORD)to

Milan (MIL)
17 May 2026 - 24 May 2026
From
$894.74
Seen: 17 hrs ago
Each way
Economy

Chicago (ORD)to

Naples (NAP)
30 Aug 2026 - 7 Sep 2026
From
$1,094.63
Seen: 6 hrs ago
Roundtrip*
Economy

Chicago (ORD)to

Venice (VCE)
12 Aug 2026 - 22 Aug 2026
From
$819.10
Seen: 9 hrs ago
Roundtrip*
Economy

Chicago (ORD)to

Milan (LIN)
5 Sep 2026 - 12 Sep 2026
From
$1,296.91
Seen: 17 hrs ago
Roundtrip*
Economy

*Roundtrip Restrictions apply.
Each way fare as part of a return trip including taxes and charges. One way fare including taxes and charges.

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Best Deals for Chicago to Italy*

Best Deals for Chicago to Italy*
From
To
Fare Type
Dates
Price
Chicago (ORD)Rome (FCO)Roundtrip*
/
Economy		20 Aug 2026 - 27 Aug 2026

From

$824.43

Seen: 21 hrs ago

Chicago (ORD)Naples (NAP)Roundtrip*
/
Economy		30 Aug 2026 - 7 Sep 2026

From

$1,094.63

Seen: 6 hrs ago

Chicago (ORD)Venice (VCE)Roundtrip*
/
Economy		12 Aug 2026 - 22 Aug 2026

From

$819.10

Seen: 9 hrs ago

Chicago (ORD)Milan (LIN)Roundtrip*
/
Economy		5 Sep 2026 - 12 Sep 2026

From

$1,296.91

Seen: 17 hrs ago

*Roundtrip Restrictions apply.
Each way fare as part of a return trip including taxes and charges. One way fare including taxes and charges.

Explore More Flights from Chicago to Italy

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Dublin (DUB)to

New York (JFK)
25 Oct 2026 - 1 Nov 2026
From
€223.09
Seen: 1 hour ago
Each way
Economy

Dublin (DUB)to

Malaga (AGP)
Depart: 24 Aug 2026
From
€76.25
Seen: 9 hrs ago
One way
Economy

Dublin (DUB)to

Orlando (MCO)
9 Jun 2026 - 22 Jun 2026
From
€252.09
Seen: 1 hour ago
Each way
Economy

Dublin (DUB)to

London (LHR)
Depart: 14 Jun 2026
From
€59.25
Seen: 55 minutes ago
One way
Economy

Dublin (DUB)to

Faro (FAO)
Depart: 15 Aug 2026
From
€76.25
Seen: 33 minutes ago
One way
Economy

Dublin (DUB)to

Paris (CDG)
Depart: 27 Aug 2026
From
€63.11
Seen: 8 hrs ago
One way
Economy

Dublin (DUB)to

Boston (BOS)
3 Jun 2026 - 13 Jun 2026
From
€225.09
Seen: 1 hour ago
Each way
Economy

London (LHR)to

Dublin (DUB)
6 Jun 2026 - 6 Jun 2026
From
£62.99
Seen: 23 hrs ago
Each way
Economy

Boston (BOS)to

Dublin (DUB)
24 Sep 2026 - 4 Oct 2026
From
$605.82
Seen: 17 hrs ago
Roundtrip*
Economy

Dublin (DUB)to

Lanzarote (ACE)
Depart: 9 Nov 2026
From
€115.25
Seen: 20 hrs ago
One way
Economy

New York (JFK)to

Dublin (DUB)
21 Aug 2026 - 8 Sep 2026
From
$564.19
Seen: 14 hrs ago
Roundtrip*
Economy

Chicago (ORD)to

Dublin (DUB)
26 Oct 2026 - 3 Nov 2026
From
$692.12
Seen: 13 hrs ago
Roundtrip*
Economy

Dublin (DUB)to

Chicago (ORD)
5 Nov 2026 - 10 Nov 2026
From
€252.59
Seen: 20 hrs ago
Each way
Economy

Dublin (DUB)to

Nashville (BNA)
17 Nov 2026 - 24 Nov 2026
From
€240.09
Seen: 14 hrs ago
Each way
Economy

Dublin (DUB)to

Toronto (YYZ)
3 Nov 2026 - 10 Nov 2026
From
€220.96
Seen: 15 hrs ago
Each way
Economy

Dublin (DUB)to

Amsterdam (AMS)
Depart: 17 Nov 2026
From
€43.25
Seen: 19 hrs ago
One way
Economy

Dublin (DUB)to

Tenerife (TFS)
Depart: 17 Nov 2026
From
€105.25
Seen: 13 hrs ago
One way
Economy

Cork (ORK)to

Malaga (AGP)
Depart: 31 Aug 2026
From
€74.37
Seen: 33 minutes ago
One way
Economy

Dublin (DUB)to

San Francisco (SFO)
4 Jun 2026 - 25 Jun 2026
From
€272.09
Seen: 5 hrs ago
Each way
Economy

Dublin (DUB)to

Los Angeles (LAX)
29 May 2026 - 8 Jun 2026
From
€262.09
Seen: 2 hrs ago
Each way
Economy