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Deals on flights from Chicago to Italy*
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Chicago (ORD)to
Rome (FCO)12 Apr 2026 - 21 Apr 2026
From
$561.25
Seen: 2 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Venice (VCE)5 Sep 2026 - 15 Sep 2026
From
$893.03
Seen: 11 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Milan (LIN)2 Apr 2026 - 7 Apr 2026
From
$1,463.01
Seen: 5 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Naples (NAP)17 Jun 2026 - 3 Jul 2026
From
$1,959.56
Seen: 6 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Milan (MIL)20 Jul 2026 - 28 Jul 2026
From
$565.66
Seen: 4 hrs ago
Each way
Economy
*Roundtrip Restrictions apply.
Each way fare as part of a return trip including taxes and charges.
Best Deals for Chicago to Italy*
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Chicago (ORD) | Rome (FCO) | Roundtrip* / Economy | 11 May 2026 - 21 May 2026 | From $561.93 Seen: 8 hrs ago |
| Chicago (ORD) | Venice (VCE) | Roundtrip* / Economy | 5 Sep 2026 - 15 Sep 2026 | From $893.03 Seen: 11 hrs ago |
| Chicago (ORD) | Milan (LIN) | Roundtrip* / Economy | 11 Nov 2026 - 17 Nov 2026 | From $518.38 Seen: 4 hrs ago |
| Chicago (ORD) | Naples (NAP) | Roundtrip* / Economy | 17 Jun 2026 - 3 Jul 2026 | From $1,959.56 Seen: 6 hrs ago |
| Chicago (ORD) | Milan (MIL) | Each way / Economy | 6 Oct 2026 - 20 Oct 2026 | From $492.48 Seen: 11 hrs ago |
*Roundtrip Restrictions apply.
Each way fare as part of a return trip including taxes and charges.
Explore More Flights from Chicago to Italy
QA FE Test Travel Dates Filter Feature Prepro
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Dublin (DUB)to
Malaga (AGP)Depart: 27 Apr 2026
From
€56.25
Seen: 23 minutes ago
One way
Economy
Dublin (DUB)to
New York (JFK)6 May 2026 - 11 May 2026
From
€225.76
Seen: 5 hrs ago
Each way
Economy
Dublin (DUB)to
Orlando (MCO)24 Apr 2026 - 6 May 2026
From
€252.76
Seen: 6 hrs ago
Each way
Economy
Boston (BOS)to
Dublin (DUB)23 Apr 2026 - 8 May 2026
From
$584.19
Seen: 15 hrs ago
Roundtrip*
Economy
Dublin (DUB)to
London (LHR)Depart: 29 Apr 2026
From
€59.25
Seen: 5 hrs ago
One way
Economy
Dublin (DUB)to
Faro (FAO)Depart: 19 Apr 2026
From
€56.25
Seen: 17 hrs ago
One way
Economy
Dublin (DUB)to
Paris (CDG)Depart: 13 Apr 2026
From
€51.25
Seen: 2 hrs ago
One way
Economy
Chicago (ORD)to
Dublin (DUB)5 May 2026 - 17 Nov 2026
From
$641.59
Seen: 13 hrs ago
Roundtrip*
Economy
New York (JFK)to
Dublin (DUB)30 Apr 2026 - 19 Nov 2026
From
$550.09
Seen: 15 hrs ago
Roundtrip*
Economy
Los Angeles (LAX)to
Dublin (DUB)20 Apr 2026 - 29 Apr 2026
From
$814.19
Seen: 18 hrs ago
Roundtrip*
Economy
Boston (BOS)to
Shannon (SNN)6 Apr 2026 - 10 Apr 2026
From
$581.78
Seen: 3 hrs ago
Roundtrip*
Economy
Dublin (DUB)to
Lanzarote (ACE)Depart: 26 Apr 2026
From
€76.25
Seen: 9 hrs ago
One way
Economy
Dublin (DUB)to
Toronto (YYZ)5 Jun 2026 - 20 Jun 2026
From
€223.32
Seen: 5 hrs ago
Each way
Economy
Dublin (DUB)to
Chicago (ORD)17 Jun 2026 - 23 Jun 2026
From
€279.76
Seen: 5 hrs ago
Each way
Economy
Cleveland (CLE)to
Dublin (DUB)14 Apr 2026 - 6 May 2026
From
$684.19
Seen: 16 hrs ago
Roundtrip*
Economy
Dublin (DUB)to
Rome (FCO)Depart: 13 Apr 2026
From
€65.25
Seen: 6 hrs ago
One way
Economy
Dublin (DUB)to
Amsterdam (AMS)Depart: 29 Apr 2026
From
€43.65
Seen: 5 hrs ago
One way
Economy
Dublin (DUB)to
Boston (BOS)22 Apr 2026 - 3 May 2026
From
€225.76
Seen: 5 hrs ago
Each way
Economy
San Francisco (SFO)to
Dublin (DUB)9 Sep 2026 - 17 Sep 2026
From
$814.19
Seen: 13 hrs ago
Roundtrip*
Economy
Raleigh (RDU)to
Dublin (DUB)13 Apr 2026 - 23 Apr 2026
From
$646.19
Seen: 5 hrs ago
Roundtrip*
Economy