Vacations from Chicago to Boston
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cmp-carousel-container-explain 7 night(s)
Boston Marriott Newton
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,386 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Hyatt Regency Boston
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,475 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Revere Hotel Boston
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,600 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Copley Square Hotel
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,605 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Hotel AKA Back Bay
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,677 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Hilton Boston Logan Airport
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,742 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Battery Wharf Hotel, Boston Waterfront
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,835 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Hotel AKA Boston Commo
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,840 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Boston Marriott Copley Place
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,858 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Renaissance Boston Waterfront Hotel
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,862 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
The Colonnade Hotel
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,876 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
The Westin Copley Place, Boston, a Marriott Hotel
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $1,961 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
The Royal Sonesta Boston
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $2,025 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
The Lenox Hotel
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $2,034 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Omni Parker House
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $2,069 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Seaport Boston Hotel
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $2,072 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Fairmont Copley Plaza
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $2,190 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
XV Beacon Boston
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $3,148 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Boston Harbor Hotel
7/05/2025 July 5, 2025
- 7/12/2025 July 12, 2025
Chicago (ORD) To Boston (BOS)
Flight + Hotel
from $3,904 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
*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.
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