Vacations Close To Orland Square
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Orland Square Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,182, price is now $842 per person
$842
per person
Dec 31 - Jan 5
found 16 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
I would say the best part was the view from the 20th floor looking right at the Magnificent Mile! The windows from ceiling to floor were awesome! The view at night was amazing! Everything was AMAZING!!
Reviewed on Nov 8, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $1,054 per person
$1,054
per person
Dec 21 - Dec 29
found 18 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Had an amazing time celebrating my wife’s birthday I will return ou room was so clean and had all the things that we needed
Reviewed on Nov 8, 2026
The Blackstone, Autograph Collection
Downtown Chicago
Price was $1,237, price is now $921 per person
$921
per person
Dec 21 - Dec 29
found 18 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Nice property but a little worn.mattresses were not that comfortable .Some staff were great, others not so much.
Reviewed on Nov 8, 2026
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
Price was $1,011, price is now $811 per person
$811
per person
Dec 31 - Jan 5
found 16 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
When we visit Chicago, this is the hotel we always book - the staff is top tier as well as our stay! It always has the most amazing views at night! Hopefully we will be back soon to visit our favorite hotel and one of our favorite cities!!
Reviewed on Nov 8, 2026
Don't see what you're looking for?
See all available trips from Columbus to Orland Square
View all tripsBest Lodging Options Near Orland Square
Holiday Inn Chicago – Midway Airport S by IHG
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 free airport shuttle. Our guests praise the helpful staff ...
Chicago Club Inn & Suites
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 ...
Sybaris Pool Suites
600 Ogden Ave Downers Grove IL
24.96 km from Orland Square
Stay at this hotel in Downers Grove. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Oakbrook Center Mall and Ty Warner Park are ...
Embassy Suites by Hilton Chicago Lombard Oak Brook
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
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 ...
Jaslin Hotel
261 West Cermak Rd Chicago IL
30.95 km from Orland Square
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
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.