Vacations from Chicago to Orlando
Flight + Hotel Packages from Minneapolis to Boston From - To
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Hilton Vacation Club Cypress Pointe Orlando
3/18/2025 March 18, 2025
- 3/23/2025 March 23, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $624 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
5 night(s)
AC Hotel Orlando Lake Buena Vista
3/18/2025 March 18, 2025
- 3/23/2025 March 23, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $749 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Legacy Vacation Resorts Disney Lake Buena Vista
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $788 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
5 night(s)
Melia Orlando Suite Hotel at Celebration
3/18/2025 March 18, 2025
- 3/23/2025 March 23, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $793 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Blue Tree Resort
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $854 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hilton Grand Vacations Club SeaWorld® Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $886 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
TRYP by Wyndham Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $902 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hilton Grand Vacations Club Parc Soleil Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $911 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hilton Orlando/Altamonte Springs
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $915 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hilton Grand Vacations Club Tuscany Village Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $919 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
5 night(s)
Hotel Kinetic Orlando Universal Blvd.
3/18/2025 March 18, 2025
- 3/23/2025 March 23, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $928 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Hilton Vacation Club Polynesian Isles Kissimmee
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $935 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
The Point Orlando Resort
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $947 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
5 night(s)
Hilton Orlando Lake Buena Vista Disney Springs
3/18/2025 March 18, 2025
- 3/23/2025 March 23, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $997 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
WorldQuest Resort
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,007 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hilton Grand Vacations Club Las Palmeras Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,016 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Renaissance Orlando Resort and Spa
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,019 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
DoubleTree by Hilton Orlando Airport
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,072 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Signia by Hilton Orlando - An Official Walt Disney World® Hotel
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,110 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Regal Oaks CLC Resort
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,112 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,137 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Marriott's Grande Vista
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,176 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hilton Orlando Buena Vista Palace - Disney Springs® Area
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,199 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Margaritaville Resort Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,214 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Heritage Haven
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,246 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hyatt Regency Orlando International Airport
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,351 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hyatt Regency Orlando
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,407 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hyatt Regency Grand Cypress
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $1,517 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Universal Helios Grand Hotel, A Loews Hotel
7/20/2025 July 20, 2025
- 7/27/2025 July 27, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $2,298 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
5 night(s)
Loews Royal Pacific Resort at Universal Orlando
3/18/2025 March 18, 2025
- 3/23/2025 March 23, 2025
Chicago (ORD) To Orlando (MCO)
Flight + Hotel
from $2,306 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 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.
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