Search Deals onOrland Square Vacation Packages
Orland Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago-Oakbrook by IHG
Price was $494, price is now $322 per person
$322
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Villa Park. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Drury Lane Theater are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Price was $1,245, price is now $607 per person
$607
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago
Price was $1,394, price is now $741 per person
$741
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Save 100% on your flight
Price was $1,021, price is now $543 per person
$543
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Price was $2,109, price is now $1,146 per person
$1,146
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hampton Inn & Suites Chicago Medical District UIC
Save 100% on your flight
Price was $948, price is now $553 per person
$553
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions United Center and Chicago Riverwalk are located nearby.
Holiday Inn Chicago O'Hare – Rosemont by IHG
Save 100% on your flight
Price was $559, price is now $329 per person
$329
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Hyatt Centric Chicago Magnificent Mile
Save 100% on your flight
Price was $1,586, price is now $968 per person
$968
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
L7 Chicago by LOTTE
Save 100% on your flight
Price was $1,287, price is now $788 per person
$788
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Chicago/Oak Lawn
Save 100% on your flight
Price was $645, price is now $401 per person
$401
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Ridge Shopping Mall and SeatGeek Stadium are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,508, price is now $942 per person
$942
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Eurostars Magnificent Mile
Save 100% on your flight
Price was $1,146, price is now $720 per person
$720
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
3-4 Night Vacations in Orland Square
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Orland Square
Price found within the past 48 hours. Click for updated prices.
Orland Square Last Minute Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Canopy by Hilton Chicago Central Loop
226 West Jackson Blvd, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the bar and the helpful ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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