Orland Square

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,146, price is now €880 per person
€880
per person
1 Feb - 6 Feb
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on 18 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €2,414, price is now €1,756 per person
€1,756
per person
19 Dec - 24 Dec
found 23 hours ago
Return flight included
Manchester (MAN) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on 17 Nov 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was €1,161, price is now €888 per person
€888
per person
1 Feb - 6 Feb
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on 28 Oct 2025

Popular places to visit

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

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

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

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue Chicago IL
Hampton Inn & Suites Chicago Medical District UIC
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
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
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
Hilton Garden Inn Chicago Downtown South Loop
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
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
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
Homewood Suites by Hilton Chicago Downtown South Loop
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
See all 5,610 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.

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