Title: Oak Park Vacation Packages & Trips 2025/2026 from CA $493 | Expedia.ca

  

[Hotels in Oak Park](https://expedia.ca/Oak-Park-Hotels.d9228.Travel-Guide-Hotels)[Vacation Rentals in Oak Park](https://expedia.ca/Oak-Park-Vacation-Rentals.d9228.Travel-Guide-VacationRentals)[Flights to Oak Park](https://expedia.ca/Cheap-Flights-To-Oak-Park.d9228.Travel-Guide-Flights)[Things to do in Oak Park](https://expedia.ca/Things-To-Do-In-Oak-Park.d9228.Travel-Guide-Activities)[Oak Park Car Rentals](https://expedia.ca/Car-Rentals-In-Oak-Park.d9228.Car-Rental-Guide)

![](https://images.trvl-media.com/place/9228/8aa55e4b-7308-4358-afcc-4ab6897c20e0.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Oak Park Vacation Packages

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

-   ## 
    
    Plan, book, travel with confidence
    

### 

Better together

Save up to CA $1,096 when you book a flight and hotel together\*

### 

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

### 

Rest easy

Plan, book, and manage your trip all in one place

#### Your Oak Park Vacation

With one of our vacation packages to Oak Park, you'll have endless opportunities for adventure and relaxation. There's a lot to experience, including its chic vibe and rich history. Want to explore your new surroundings? [United Center](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction), [Brookfield Zoo](https://www.expedia.ca/Brookfield-Zoo-Chicago.d6064025.Vacation-Attraction) and [Portage Park](https://www.expedia.ca/Portage-Park-Portage-Park.d6069237.Vacation-Attraction) are just three of the leading places to visit during your trip to Oak Park. No matter your travel plans or budget, putting together the ultimate tailored Oak Park vacation is a walk in the park with Expedia.

## Top Oak Park Vacation Deals

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

![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 $493

per person

Nov 24 - Nov 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (291 reviews)

Food price was high but everything was fine

Reviewed on Oct 4, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvmPhJEHj3yUa4pQjpLBPOPD-BnEOz5Ktyz_Zg1RwtFT3)

![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Michigan Avenue Chicago

Downtown Chicago

CA $1,012

per person

Dec 24 - Dec 29

found 12 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

8.8/10 Excellent! (1,046 reviews)

One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-29/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O6rtfnKeYzdCF2LvQdCFU0DQ1KxnriIfcqvo9-5kFJQk)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,258

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=YlgsqDC9o72ZmKi_PcaxVzT9EdRsJi0kOxnMb0QvNm_EWriKf0xB3Uv-jBJ6XUIX)

![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 $713

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on Oct 7, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=YlgsqDC9o72ZmKi_PcaxV1LfcL3n7DcHtClVk-zae6ucVb4symUP2TW4ALTy7UDI)

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Swissotel - Chicago

Downtown Chicago

CA $639

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on Oct 9, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17288&paandie=true&dealMarker=YlgsqDC9o72ZmKi_PcaxVz4SMZt9AJY0Q69eMBUnbsCSWK_G2XqbLyEhxd41VjAU)

## Ready to book your vacation to Oak Park?

Choose your dates

## Oak 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 $179

CA $210 total

Nov 2 - Nov 3

includes taxes & fees

7.8/10 Good! (9,342 reviews)

"We did not use laundry service, and the front desk staff did not mention any availbale services"

Reviewed on Oct 7, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=9228)

![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 $95

CA $137 total

Nov 11 - Nov 12

includes taxes & fees

7.8/10 Good! (2,426 reviews)

"Excellent location, clean and good room partners"

Reviewed on Oct 6, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true&regionId=9228)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $213

CA $250 total

Nov 9 - Nov 10

includes taxes & fees

8.4/10 Very Good! (5,072 reviews)

"The onsite parking is worth the money compared to other lots. Walk where you can. The Embassy is in the perfect location for a lot of attractions."

Reviewed on Oct 9, 2025

[](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=9228)

[See all 4,916 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F10%2F2025&endDate=13%2F10%2F2025&regionId=9228)

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 Oak 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 Oak 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 $67

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 $77

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 Oak Park](https://expedia.ca/things-to-do/search?rid=9228)

## Explore a world of travel with Expedia

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

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