Search Deals on
Orland Square Vacation Packages

Orland Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Rolling Meadows, IL - Chicago Northwest

Motel 6 Rolling Meadows, IL - Chicago Northwest

2 out of 5
per person
Jun 5 - Jun 9
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this motel in Rolling Meadows. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Arlington International Racecourse are located nearby.
Motel 6 Libertyville, IL

Motel 6 Libertyville, IL

2 out of 5
per person
Jun 5 - Jun 9
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this motel in Libertyville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Six Flags Great America and Gurnee Mills are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 22 - May 26
found 8 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly 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 United Center and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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.
Comfort Inn Gurnee near Six Flags

Comfort Inn Gurnee near Six Flags

2.5 out of 5
per person
Jun 5 - Jun 9
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. 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.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 3-star business-friendly 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool 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.
Dorothy's

Dorothy's

3 out of 5
Lakeview
per person
May 19 - May 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Motel 6 Libertyville, IL

Motel 6 Libertyville, IL

2 out of 5
per person
Jun 5 - Jun 9
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 23
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hampton Inn & Suites Chicago/Hoffman Estates

Hampton Inn & Suites Chicago/Hoffman Estates

2.5 out of 5
per person
Jun 5 - Jun 9
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)

5-7 Night Vacations in Orland Square

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)

Orland Square Last Minute Hotel Deals

Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
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 ...
Crowne Plaza Chicago West Loop by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
Stay at this 3.5-star aparthotel in Chicago. Enjoy a fitness center, concierge services, and in-room washers/dryers. Popular attractions Soldier Field and Grant ...
Sonder South Wabash
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
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 ...
Congress Plaza Hotel
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
Best Western Grant Park Hotel
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
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 ...
Holiday Inn & Suites Chicago - Downtown by IHG
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop
3 out of 5
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 ...
Hilton Garden Inn Chicago Downtown South Loop
Hilton Chicago
Hilton Chicago
4 out of 5
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 Chicago
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop
3 out of 5
59 E. 11th Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Homewood Suites by Hilton Chicago Downtown South Loop
See all 4,969 properties in Orland Square
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.