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Deals on flights from Chicago to Italy*
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Chicago (ORD)to
Rome (FCO)16 Apr 2026 - 24 Apr 2026
From
$616.76
Seen: 2 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Milan (LIN)17 Apr 2026 - 29 Apr 2026
From
$670.54
Seen: 19 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Venice (VCE)29 Apr 2026 - 7 May 2026
From
$688.13
Seen: 23 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Milan (MIL)5 May 2026 - 20 May 2026
From
$351.93
Seen: 4 hrs ago
Each way
Economy
Chicago (ORD)to
Naples (NAP)7 Apr 2026 - 22 Apr 2026
From
$651.65
Seen: 19 hrs ago
Roundtrip*
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 | 27 Oct 2026 - 10 Nov 2026 | From $537.01 Seen: 18 hrs ago |
| Chicago (ORD) | Milan (LIN) | Roundtrip* / Economy | 17 Apr 2026 - 29 Apr 2026 | From $670.54 Seen: 19 hrs ago |
| Chicago (ORD) | Venice (VCE) | Roundtrip* / Economy | 29 Apr 2026 - 7 May 2026 | From $688.13 Seen: 23 hrs ago |
| Chicago (ORD) | Milan (MIL) | Each way / Economy | 5 May 2026 - 20 May 2026 | From $351.93 Seen: 4 hrs ago |
| Chicago (ORD) | Naples (NAP) | Roundtrip* / Economy | 7 Apr 2026 - 22 Apr 2026 | From $651.65 Seen: 19 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
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QA FE Test Travel Dates Filter Feature Prepro
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Dublin (DUB)to
New York (JFK)8 Feb 2026 - 17 Feb 2026
From
€174.00
Seen: 44 minutes ago
Each way
Economy
Dublin (DUB)to
Malaga (AGP)Depart: 27 Apr 2026
From
€40.60
Seen: 35 minutes ago
One way
Economy
Dublin (DUB)to
Orlando (MCO)5 Feb 2026 - 12 Feb 2026
From
€214.00
Seen: 38 minutes ago
Each way
Economy
Dublin (DUB)to
Lanzarote (ACE)Depart: 24 Feb 2026
From
€61.00
Seen: 7 hrs ago
One way
Economy
Dublin (DUB)to
Paris (CDG)Depart: 31 Mar 2026
From
€35.60
Seen: 10 minutes ago
One way
Economy
Dublin (DUB)to
London (LHR)Depart: 25 Mar 2026
From
€55.00
Seen: 47 minutes ago
One way
Economy
Dublin (DUB)to
Amsterdam (AMS)Depart: 9 Mar 2026
From
€28.00
Seen: 52 minutes ago
One way
Economy
Dublin (DUB)to
Faro (FAO)Depart: 13 Apr 2026
From
€40.60
Seen: 3 hrs ago
One way
Economy
Dublin (DUB)to
Tenerife (TFS)Depart: 29 Apr 2026
From
€60.60
Seen: 20 hrs ago
One way
Economy
New York (JFK)to
Dublin (DUB)10 Mar 2026 - 25 Mar 2026
From
$408.87
Seen: 23 hrs ago
Roundtrip*
Economy
Dublin (DUB)to
Rome (FCO)Depart: 10 Mar 2026
From
€41.00
Seen: 13 minutes ago
One way
Economy
Dublin (DUB)to
Barcelona (BCN)Depart: 12 Apr 2026
From
€35.60
Seen: 1 hour ago
One way
Economy
Manchester (MAN)to
Orlando (MCO)16 Feb 2026 - 24 Feb 2026
From
£475.89
Seen: 4 minutes ago
Roundtrip*
Economy
Dublin (DUB)to
Boston (BOS)13 Feb 2026 - 19 Feb 2026
From
€174.00
Seen: 31 minutes ago
Each way
Economy
Manchester (MAN)to
New York (JFK)27 Feb 2026 - 10 Mar 2026
From
£429.49
Seen: 6 hrs ago
Roundtrip*
Economy
Boston (BOS)to
Dublin (DUB)17 Feb 2026 - 27 Feb 2026
From
$408.87
Seen: 20 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Dublin (DUB)3 Mar 2026 - 10 Mar 2026
From
$470.87
Seen: 18 hrs ago
Roundtrip*
Economy
Dublin (DUB)to
Manchester (MAN)Depart: 12 Feb 2026
From
€25.00
Seen: 57 minutes ago
One way
Economy
Dublin (DUB)to
Cancun (CUN)Depart: 19 Mar 2026
From
€496.77
Seen: 21 hrs ago
One way
Economy
Dublin (DUB)to
Toronto (YYZ)26 Feb 2026 - 3 Mar 2026
From
€194.92
Seen: 39 minutes ago
Each way
Economy