Title: Oak Park Vacation Packages & Trips 2026 from CA $747 | 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/f6f88e06-f8a7-4edb-b5d7-6cc04a9c058c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Oak Park Vacation Packages

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#### 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.

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $747

per person

Jun 13 - Jun 15

found 10 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (3,688 reviews)

This is a gem. The staff were caring, welcoming and accommodating. The property is at a perfect location with many eating and shopping options. The bus stop was feet away and access to the metro a couple blocks away. Breakfast was great; it had a great selection of food. Negative: I tried modifying my reservation a couple weeks prior my stay, after noticing a mistake made at the time of booking. However, I was unable to reach anyone at tye hotel, over the phone. Later, I was told by the site I booked my stay, that the hotel denied the request. I will definitely go back to this hotel!

Reviewed on Apr 5, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,154

per person

Jun 18 - Jun 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

I enjoyed this property and the view is top notch

Reviewed on Apr 6, 2026

![Staybridge Suites, Lincolnshire by IHG](https://images.trvl-media.com/lodging/1000000/930000/921900/921866/6b7025ef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Staybridge Suites, Lincolnshire by IHG

Half Day

CA $866

per person

May 20 - May 27

found 7 hours ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

Breakfast was fresh, parking was easy, stay was amazing!! Will definitely be staying again!

Reviewed on Apr 4, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,227

per person

May 23 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,005 reviews)

The staff were wonderful, the room was beautiful, and the location was fantastic. I really wanted to love this hotel. Unfortunately, two issues made for a difficult stay. The noise was severe. Despite being listed as soundproof, our junior suite on the 10th floor was incredibly loud. We’ve stayed in many major cities (and lived in some). But have not experienced this level of disruption from sirens, car alarms, horns, and blasting music from passersby all night. The blackout curtains are thin and don't reach the floor, offering little sound buffering. This is a far cry from the double-glazed windows and heavy drapes you'd expect from a hotel marketing itself as soundproof. The motion-sensor system controlling all lights and HVAC was also a safety concern. If you're still for too long (say, soaking in the bathtub), the entire room goes pitch black. Even the bathroom night light turns off on a timer. We asked the staff to disable this, and they said they did, but the problem persisted. For the price of a 5-star hotel, these issues brought the experience down to a 3-star stay. It's a shame, because so much else was genuinely excellent. We’d return, but only if these issues are addressed.

Reviewed on Apr 5, 2026

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $3,433

per person

May 20 - May 27

found 7 hours ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

9.8/10 Exceptional! (1,010 reviews)

Excellent room and facilities. Helpfull staff and amazing locstion.

Reviewed on Mar 27, 2026

## Ready to book your vacation to Oak Park?

Choose your dates

## Oak Park Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_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 $151

CA $177 total

Apr 16 - Apr 17

includes taxes & fees

8/10 Very Good! (10,037 reviews)

Property is always well maintained, very clean and tidy

Reviewed on Apr 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=9228)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Fully refundableReserve now, pay when you stay

CA $191

CA $224 total

Apr 12 - Apr 13

includes taxes & fees

9/10 Wonderful! (4,063 reviews)

Amazing hotel, felt like a star in my suite! Accessible location and wonderful welcoming staff made this some place I wish we had stayed more than one night.

Reviewed on Apr 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=9228)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Fully refundableReserve now, pay when you stay

CA $205

CA $240 total

Apr 27 - Apr 28

includes taxes & fees

8.6/10 Excellent! (5,824 reviews)

The room was very clean but the amenities are quite dirty. In general is a big hotel with a lot of movement, many families and a lot of people everywhere, so the breakfast (which is great by the way) is very busy.

Reviewed on Apr 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=27%2F04%2F2026&endDate=28%2F04%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=9228)

[See all 5,035 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&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](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

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)

![Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format](https://images.trvl-media.com/place/6069213/2e400cca-d4de-4424-b8be-c4a1fa3a5d7a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. 

[](https://expedia.ca/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction)

![Navy Pier](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

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

![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 360 CHICAGO Observation Deck

CA $37

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details)

![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wendella's 90-min Chicago River Architecture Tour

CA $55

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details)

![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Flyover in Chicago

CA $52

per adult

**98%** of travellers recommend

[](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details)

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

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