Search Deals onOrland Square Vacation Packages
Orland Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.


Super 8 by Wyndham Deerfield/Northbrook
per person
Sep 3 - Sep 10
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Deerfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sportsman's Country Club and Northbrook Sports Complex are located nearby.

Howard Johnson by Wyndham Waukegan Great Lakes
per person
Sep 3 - Sep 10
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Waukegan. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Six Flags Great America and Gurnee Mills are located nearby.

Super 8 by Wyndham South Holland
per person
Sep 3 - Sep 10
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in South Holland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Midwest Carvers Museum and Harvey Public Library are located nearby.

Park Hyatt Chicago
Save 100% on your flight
per person
Sep 11 - Sep 15
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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Sep 11 - Sep 15
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.

citizenM Chicago Downtown
Save 100% on your flight
per person
Sep 11 - Sep 15
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 a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
per person
Sep 11 - Sep 15
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.

Arlo Chicago
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Fairmont Chicago at Millennium Park
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Hilton Garden Inn Chicago Central Loop
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Institute of Chicago and Millennium Park are located nearby.

Canopy by Hilton Chicago Central Loop
Save 100% on your flight
per person
Sep 11 - Sep 15
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 a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park 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 ...

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, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...

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 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 ...

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 ...

Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...

Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE, Chicago, IL
Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...
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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