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Deals on flights from Chicago to Italy*
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Chicago (ORD)to
Rome (FCO)May 11 2026 - May 20 2026
From
$561.12
Seen: 5 minutes ago
Roundtrip*
Economy
Chicago (ORD)to
Venice (VCE)Aug 30 2026 - Sep 17 2026
From
$801.64
Seen: 12 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Milan (LIN)Sep 12 2026 - Sep 26 2026
From
$941.88
Seen: 12 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Naples (NAP)Sep 8 2026 - Sep 18 2026
From
$916.39
Seen: 3 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Milan (MIL)Sep 10 2026 - Sep 18 2026
From
$380.10
Seen: 10 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 | May 11 2026 - May 20 2026 | From $561.12 Seen: 5 minutes ago |
| Chicago (ORD) | Venice (VCE) | Roundtrip* / Economy | Aug 30 2026 - Sep 17 2026 | From $801.64 Seen: 12 hrs ago |
| Chicago (ORD) | Milan (LIN) | Roundtrip* / Economy | Nov 11 2026 - Nov 17 2026 | From $517.60 Seen: 6 hrs ago |
| Chicago (ORD) | Naples (NAP) | Roundtrip* / Economy | Sep 8 2026 - Sep 18 2026 | From $916.39 Seen: 3 hrs ago |
| Chicago (ORD) | Milan (MIL) | Each way / Economy | Sep 10 2026 - Sep 18 2026 | From $380.10 Seen: 10 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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Boston (BOS)to
Shannon (SNN)May 8 2026 - May 11 2026
From
$509.56
Seen: 14 hrs ago
Roundtrip*
Economy
Cleveland (CLE)to
Dublin (DUB)Sep 23 2026 - Oct 1 2026
From
$445.20
Seen: 2 hrs ago
Roundtrip*
Economy
Pittsburgh (PIT)to
Dublin (DUB)Sep 7 2026 - Sep 14 2026
From
$574.96
Seen: 12 hrs ago
Roundtrip*
Economy
Washington, D.C. (IAD)to
Dublin (DUB)Sep 1 2026 - Sep 7 2026
From
$574.96
Seen: 11 hrs ago
Roundtrip*
Economy
Hartford (BDL)to
Dublin (DUB)Sep 5 2026 - Sep 11 2026
From
$544.96
Seen: 11 hrs ago
Roundtrip*
Economy
Nashville (BNA)to
Dublin (DUB)May 6 2026 - May 12 2026
From
$672.96
Seen: 11 hrs ago
Roundtrip*
Economy
New York (JFK)to
Shannon (SNN)Sep 9 2026 - Sep 18 2026
From
$509.56
Seen: 10 hrs ago
Roundtrip*
Economy
Denver (DEN)to
Dublin (DUB)May 4 2026 - May 11 2026
From
$669.96
Seen: 12 hrs ago
Roundtrip*
Economy
Boston (BOS)to
Dublin (DUB)Sep 10 2026 - Sep 14 2026
From
$509.96
Seen: 21 hrs ago
Roundtrip*
Economy
Orlando (MCO)to
Dublin (DUB)May 6 2026 - May 13 2026
From
$673.10
Seen: 5 hrs ago
Roundtrip*
Economy
Chicago (ORD)to
Dublin (DUB)Sep 21 2026 - Dec 11 2026
From
$590.90
Seen: 20 hrs ago
Roundtrip*
Economy
New York (JFK)to
Dublin (DUB)May 6 2026 - May 12 2026
From
$509.96
Seen: 23 hrs ago
Roundtrip*
Economy
Raleigh (RDU)to
Dublin (DUB)Sep 7 2026 - Sep 15 2026
From
$594.96
Seen: 16 hrs ago
Roundtrip*
Economy
San Francisco (SFO)to
Dublin (DUB)May 9 2026 - May 13 2026
From
$739.96
Seen: 22 hrs ago
Roundtrip*
Economy
Los Angeles (LAX)to
Dublin (DUB)May 1 2026 - May 9 2026
From
$739.96
Seen: 20 hrs ago
Roundtrip*
Economy
Indianapolis (IND)to
Dublin (DUB)Sep 2 2026 - Sep 9 2026
From
$672.96
Seen: 23 hrs ago
Roundtrip*
Economy
Seattle (SEA)to
Dublin (DUB)Sep 9 2026 - Sep 16 2026
From
$719.96
Seen: 23 hrs ago
Roundtrip*
Economy
New York/Newark (EWR)to
Dublin (DUB)May 7 2026 - May 11 2026
From
$509.96
Seen: 23 hrs ago
Roundtrip*
Economy
Philadelphia (PHL)to
Dublin (DUB)May 2 2026 - May 7 2026
From
$594.96
Seen: 21 hrs ago
Roundtrip*
Economy
Minneapolis (MSP)to
Dublin (DUB)Sep 5 2026 - Sep 15 2026
From
$553.96
Seen: 23 hrs ago
Roundtrip*
Economy