Vacations Close To Orland Square

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Orland Square Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $785, price is now $543 per person
$543
per person
Nov 1 - Nov 6
found 10 hours 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 $1,094, price is now $686 per person
$686
per person
Nov 1 - Nov 6
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious

Reviewed on Sep 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,075, price is now $1,307 per person
$1,307
per person
Nov 1 - Nov 6
found 12 hours 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 $1,362, price is now $952 per person
$952
per person
Nov 1 - Nov 6
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Very nice rooms, comfortable and spacious Great amenities, level 2 lobby lounge is an excellent space with great views to the exterior, Breakfast was always good and Bars are really a very nice options, roof top is great Our stay was excellent as the hotel, staff is very friendly and professional Thanks London House Hotel

Reviewed on Sep 22, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,178, price is now $851 per person
$851
per person
Nov 1 - Nov 6
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,076, price is now $1,503 per person
$1,503
per person
Nov 1 - Nov 7
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on Sep 20, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $868, price is now $629 per person
$629
per person
Nov 1 - Nov 6
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,647, price is now $1,201 per person
$1,201
per person
Nov 1 - Nov 6
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

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Best Lodging Options Near Orland Square

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
17.48 km from Orland Square
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 and ...
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
23.25 km from Orland Square
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
27.64 km from Orland Square
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
33.51 km from Orland Square
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 ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
34.64 km from Orland Square
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
33.24 km from Orland Square
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 ...
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
31.65 km from Orland Square
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
33.56 km from Orland Square
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
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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.