Orland Square Tours and Activities

Plan a trip to see Orland Square

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 23 - Oct 26
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)
Moments after arriving the hotel room, I took a shower and when I got out, there was a cockroach on my floor near the bed.

Reviewed on Aug. 7, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
The location of the hotel right off Michigan Avenue was perfect. Public parking right across the street. The hotel is fresh and new. Many staff available to assist. Do not skip the complimentary breakfast! I would easy pay $20 for that breakfast as it had everything from fresh fruit, real eggs, pastries, even a coffee cream warmer/frother machine for the great coffee!

Reviewed on Aug. 6, 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

Though University Of Chicago Medicine might be what brings you to town, perhaps you'll have a chance to explore more of Orland Park while you are here.

University Of Chicago Medicine

Centennial Park Aquatic Center

Enjoy the thrill rides with your kiddos at Centennial Park Aquatic Center as part of your trip 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 theater 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

Best Lodging Options Near Orland Square

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
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
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.