Vacations from New York to Chicago
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The Chicago Hotel Collection - Magnificent Mile
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $643 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Ambassador Hotel Chicago
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $686 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hyatt Regency Lisle near Naperville
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $687 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hilton Chicago/Oak Lawn
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $749 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Sheraton Suites Chicago O'Hare
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $914 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Renaissance Chicago O'Hare Suites Hotel
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $983 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hotel Lincoln
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $983 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hotel Riu Plaza Chicago
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,081 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
21c Museum Hotel Chicago
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,091 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
The Wade
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,160 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Marriott Chicago O'Hare
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,194 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Sophy Hyde Park
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,330 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
InterContinental Chicago Magnificent Mile by IHG
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,375 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hyatt Regency Chicago
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,389 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Swissotel Chicago
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,469 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
The Royal Sonesta Chicago Downtown
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,489 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Palmer House a Hilton Hotel
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,748 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Pendry Chicago
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $1,785 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Park Hyatt Chicago
5/05/2025 May 5, 2025
- 5/10/2025 May 10, 2025
New York (JFK) To Chicago (ORD)
Flight + Hotel
from $2,205 * 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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