Title: Orland Park Vacation Packages & Trips 2025/2026 from CA $725 | Expedia.ca

  

[Orland Park Travel Guide](https://expedia.ca/Orland-Park.dx9270)[Hotels in Orland Park](https://expedia.ca/Orland-Park-Hotels.d9270.Travel-Guide-Hotels)[Vacation Rentals in Orland Park](https://expedia.ca/Orland-Park-Vacation-Rentals.d9270.Travel-Guide-VacationRentals)[Orland Park Car Rentals](https://expedia.ca/Car-Rentals-In-Orland-Park.d9270.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Orland Park Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

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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](https://www.expedia.ca/Orland-Park-Sportsplex-Orland-Park.d6247361.Vacation-Attraction), [Orland Square](https://www.expedia.ca/Orland-Square-Chicago.d553248635976375725.Vacation-Attraction) and [Centennial Park](https://www.expedia.ca/Centennial-Park-Orland-Park.d6247339.Vacation-Attraction) 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.

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $725

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rzu2FdAJtOQBd8gfIaPecgk2EKCE3ku8zzaJQTH3gY6We)

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $971

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=qgNx3gK80nWwTZhFUtG94B4y9nNG9EwM1y1arGXZ9VG9Ijqf-H9bL3O-oTLxb-zz)

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $739

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

7.6/10 Good! (1,003 reviews)

The location of the Orrington is excellent but the star of the Orrington is delfinitely its staff. They were friendly, helpful and handled busy and problem situations with grace and solutions. Gotta love the midwest!

Reviewed on Oct 10, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-06/2025-12-13/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19722&paandie=true&dealMarker=3N3YfoFxJicbUeztIgTC6hfzVmi5aSNz5ECQtpmwsBZQChXUXwTmZpWT2iadbB6L)

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $978

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (367 reviews)

We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue. However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).

Reviewed on Oct 22, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rzkvOUKgcOmO_ruo-cBEVcsqs2DhAmzQVERuZxaX5fR9t)

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $811

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (303 reviews)

Food price was high but everything was fine

Reviewed on Oct 4, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rzkvOUKgcOmO_ruo-cBEVcsrRLDfe-kuccNWidt_IbukM)

## Ready to book your vacation to Orland Park?

Choose your dates

## Orland Park Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $131

CA $154 total

Nov 24 - Nov 25

includes taxes & fees

7.8/10 Good! (9,498 reviews)

The website for the gazebo restaurant within the hotel said there was an extensive menu. When you get down to the place it’s a small buffett set up which was similar to any other continental breakfast with some cereal, muffins, fruit, some biscuits, bacon and sausage etc. There was also a man at ...

Reviewed on Oct 20, 2025

[](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=9270)

![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Chicago Dwtn - The Mart by IHG

350 West Wolf Point Plaza, Building 2, Chicago, IL

Fully refundable

CA $194

CA $228 total

Nov 23 - Nov 24

includes taxes & fees

8.8/10 Excellent! (1,943 reviews)

Great location if you have meetings at the Mart which you can reach through escalator and a bridge that takes you directly to the second floor. The hotel is well run Good breakfast and friendly staff. Rooms are clean but they should start “refreshing” some of the features like carpets which seem ...

Reviewed on Oct 13, 2025

[](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=5467&PinnedHotelID=5467&HadPinnedHotel=true&regionId=9270)

![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Freehand Chicago

19 East Ohio Street, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $102

CA $145 total

Nov 24 - Nov 25

includes taxes & fees

7.8/10 Good! (2,508 reviews)

Very accessible location and amazing staff.

Reviewed on Oct 21, 2025

[](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true&regionId=9270)

[See all 3,323 properties in Orland Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025&regionId=9270)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Orland Park

![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

4.5/5(19 reviews)

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.

[](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)

### What to do in Orland Park

![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Architecture River Tour

CA $68

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details)

![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Architecture Center River Cruise aboard First Lady

CA $78

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

[See all activities in Orland Park](https://expedia.ca/things-to-do/search?rid=9270)

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![QR code to download the app](data:image/png;base64,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)