Orland Square

Plan a trip to see Orland Square

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
I booked a room with the water view, when I checked in I asked before I get the key, Is it a water view. They told me it is. I show up in my room and it’s not the room I booked. I called the front desk and they’re telling me we apologize all of the rooms are booked with the water view. They also said booking a water view room doesn’t guarantee a water view room even though I paid extra for a water view room! Never going to stay there again for sure.

Reviewed on 3 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
21 Sept - 25 Sept
found 22 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Popular places to visit

Space Golf

Enjoy a round of golf in Orland Park at Space Golf. Experience the great live music or attend a sporting event in this family-friendly area.

Space Golf

University Of Chicago Medicine

If University Of Chicago Medicine is what brings you to town, hopefully you'll have a chance to explore more of Orland Park.

University Of Chicago Medicine

Centennial Park Aquatic Center

Enjoy a fun-filled day at Centennial Park Aquatic Center during your visit to Orland Park. Experience the great live music or attend a sporting event in this family-friendly area.

Centennial Park Aquatic Center

Centennial Park

Explore the great outdoors at Centennial Park, a lovely green space in Orland Park. Experience the great live music or attend a sporting event in this family-friendly area.

Centennial Park

Orland Park Sportsplex

Take the family on an outing to Orland Park Sportsplex during your trip to Orland Park. Experience the area's acclaimed theatre scene and great live music.

Orland Park Sportsplex

Bremen Grove Dog Park

After visiting Bremen Grove Dog Park, make a plan to see the other sights and activities in Tinley Park. While you're in the area, wander around the forests.

Bremen Grove Dog Park

Top Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Congress Plaza Hotel
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Jaslin Hotel
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
Crowne Plaza Chicago West Loop by IHG
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Palmer House a Hilton Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Hilton Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
Holiday Inn & Suites Chicago - Downtown by IHG
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Best Western Grant Park Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
Travelodge by Wyndham Downtown Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Embassy Suites by Hilton Chicago Downtown River North
See all 5,521 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.