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Orland Square Vacation Packages

Orland Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Save 100% on your flight
Price was $483, price is now $344 per person
$344
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $633, price is now $403 per person
$403
per person
Mar 21 - Mar 25
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 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,246, price is now $826 per person
$826
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $529, price is now $377 per person
$377
per person
Mar 10 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park 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
Price was $670, price is now $480 per person
$480
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Save 100% on your flight
Price was $506, price is now $366 per person
$366
per person
Mar 21 - Mar 25
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. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
Price was $649, price is now $470 per person
$470
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $805, price is now $584 per person
$584
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Holiday Inn Express & Suites Zion by IHG

Holiday Inn Express & Suites Zion by IHG

2.5 out of 5
Price was $476, price is now $349 per person
$349
per person
Mar 10 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Carmel Park and Ophir Park are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $608, price is now $446 per person
$446
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,354, price is now $1,001 per person
$1,001
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $715, price is now $531 per person
$531
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

3-4 Night Vacations in Orland Square

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $483, price is now $344 per person
$344
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,246, price is now $826 per person
$826
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $595, price is now $404 per person
$404
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $506, price is now $366 per person
$366
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Orland Square

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $529, price is now $377 per person
$377
per person
Mar 10 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,139, price is now $723 per person
$723
per person
Mar 14 - Mar 19
found 4 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,587, price is now $1,038 per person
$1,038
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,184, price is now $853 per person
$853
per person
Mar 14 - Mar 19
found 4 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

Orland Square Last Minute Hotel Deals

The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
Book a stay at this boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
The Champagne Lodge & Luxury Suites
Sybaris Pool Suites

Sybaris Pool Suites

2.5 out of 5
600 Ogden Ave Downers Grove IL
Stay at this hotel in Downers Grove. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions Ty Warner Park and Yorktown Shopping Center ...
Sybaris Pool Suites
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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Hilton Chicago
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
500 South Dearborn Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
Book a stay at this 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
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
Book a stay at this 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
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
Book a stay at this 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
See all 5,845 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.