Chicago vacation packages
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cmp-carousel-container-explain 7 night(s)
Hyatt Regency Lisle near Naperville
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $1,403 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Renaissance Chicago O'Hare Suites Hotel
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $1,942 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Hyatt Regency O'Hare Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $1,775 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Sheraton Suites Chicago O'Hare
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $1,754 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Marriott Chicago O'Hare
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,331 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
The Westin Michigan Avenue Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,027 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Swissotel - Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $3,054 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Hotel Lincoln, Part of JDV by Hyatt
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,192 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Hotel Riu Plaza Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,980 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Palmer House a Hilton Hotel
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $3,063 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
InterContinental Chicago Magnificent Mile by IHG
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,925 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
The Wade
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,723 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
The Royal Sonesta Chicago Downtown
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,982 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Hyatt Regency Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,836 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Pendry Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $3,293 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Sophy Hyde Park
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $2,915 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Holiday Inn Chicago - Schaumburg by IHG
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $1,396 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Sheraton Suites Chicago Elk Grove
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $1,421 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Crowne Plaza Lombard Downers Grove by IHG
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $1,429 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Thompson Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $3,473 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Park Hyatt Chicago
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $3,536 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Hyatt Centric Chicago Magnificent Mile
10/06/2025 October 6, 2025
- 10/13/2025 October 13, 2025
Dallas-Fort Worth (DFW) To Chicago (ORD)
Flight + Hotel
from $3,503 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
5 night(s)
21c Museum Hotel Chicago
6/21/2025 June 21, 2025
- 6/26/2025 June 26, 2025
Charlotte (CLT) To Chicago (ORD)
Flight + Hotel
from $933 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
The Blackstone, Autograph Collection
6/21/2025 June 21, 2025
- 6/26/2025 June 26, 2025
Charlotte (CLT) To Chicago (ORD)
Flight + Hotel
from $1,161 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 21 hours ago
5 night(s)
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: 5 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: 5 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: 5 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.
