Orland Park Vacation Packages
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Your Orland Park Vacation
Get ready to experience Orland Park on your terms with a custom Orland Park vacation package! Discovering the treasures of this lively city is easy with a base in a neighborhood such as Flossmoor, which is great for golfing, among lots of other things. Like to get out and explore? Orland Park Sportsplex, Orland Square and Centennial Park are just a few of the most popular places to visit during a trip to Orland Park. Stop dreaming and start doing. Browse the broad range of options on Expedia today and finally put your Orland Park vacation plans into gear!
Top Orland Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,246, price is now CA $789 per person
CA $789
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on Aug. 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,635, price is now CA $991 per person
CA $991
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
I can honestly say that this hotel exceeded all expectations. Everything was fabulous
Reviewed on Sep. 1, 2025
The Emily Hotel
Downtown Chicago
Price was CA $1,667, price is now CA $1,061 per person
CA $1,061
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
We have stayed at The Emily Hotel twice and has become our go to for our yearly trip for an event in town. Every time we visit the staff goes above and beyond to ensure a great experience from check in, valet parking, amenities, and room service.
Reviewed on Sep. 2, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,350, price is now CA $876 per person
CA $876
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025
Pendry Chicago
Downtown Chicago
Price was CA $3,015, price is now CA $1,971 per person
CA $1,971
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Room was very nice and clean. Great location and we were able to walk almost everywhere we wanted to go. Staff was friendly and knowledgeable. Only thing I would say is that it is a little loud at night but you are downtown right off Michigan ave so you should expect some street noise. Would definitely stay here again.
Reviewed on Sep. 2, 2025
Orland Park Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Sep 3 to Sep 4
CA $194
CA $228 total
Sep 3 - Sep 4
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Sep 4 to Sep 5
CA $231
CA $272 total
Sep 4 - Sep 5
includes taxes & fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Sep 4 to Sep 5
CA $230
CA $270 total
Sep 4 - Sep 5
includes taxes & fees
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.
Discover the most popular places to visit in Orland Park
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Orland Park
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
CA $62
per adult
96% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.