Vacations from Chicago to Italy
Flight + Hotel Packages from Cleveland to Hilton Head Island From - To Anywhere
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cmp-carousel-container-explain 7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,160 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,174 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,192 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,205 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,205 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,233 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,266 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,281 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,287 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,289 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,322 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,323 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,358 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,372 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
7 night(s)
Chicago (ORD) To Naples (NAP)
2/16/2025 February 16, 2025
- 2/23/2025 February 23, 2025
Flight + Hotel
from $1,372 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,410 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,449 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,456 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,461 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,462 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,493 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,510 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,533 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,536 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,541 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,572 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,574 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,575 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,607 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
Chicago (ORD) To Venice (VCE)
9/24/2025 September 24, 2025
- 9/29/2025 September 29, 2025
Flight + Hotel
from $1,617 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
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*Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays. Prices displayed have been collected within the last 24 hrs and may no longer be available at time of booking. Modifying this information may result in a different price. To find the most updated price, please visit aavacations.com.