Title: Oak Park Vacation Packages & Trips 2026 from CA $1,459 | 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

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

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

![Hotel 55 Chicago Downtown](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/w4000h2662x0y0-2cdbdb6f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel 55 Chicago Downtown

Downtown Chicago

CA $1,459

per person

Apr 10 - Apr 17

found 21 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

8.8/10 Excellent! (1,574 reviews)

We stayed during Valentine’s Day weekend. The hotel was in a great location near restaurants and Michigan Ave for shopping. The room was very clean, the only one thing I’d like would be more sound proof windows. We heard constant ambulance/sirens and honking throughout the night.

Reviewed on Feb 24, 2026

![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 $1,714

per person

May 15 - May 18

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (3,438 reviews)

Property is excellent and always clean

Reviewed on Mar 7, 2026

![Kimpton Gray Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13360000/13351500/13351499/9bf8883a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kimpton Gray Hotel by IHG

Downtown Chicago

CA $1,978

per person

Apr 10 - Apr 17

found 21 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.2/10 Wonderful! (1,000 reviews)

Amazing hotel, amazing location

Reviewed on Mar 6, 2026

![Le Méridien Essex Chicago](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Le Méridien Essex Chicago

Downtown Chicago

CA $1,572

per person

May 15 - May 18

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

8.8/10 Excellent! (1,001 reviews)

Every activity I did was no further than 10 minutes away from the hotel.

Reviewed on Mar 7, 2026

![Hotel Arista](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141763/a6c36a1d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Arista

CA $1,502

per person

Apr 10 - Apr 17

found 21 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

Room was clean, staff was friendly and parking was really easy. Very comfortable stay.

Reviewed on Mar 5, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_9228)

## 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)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $131

CA $154 total

Mar 30 - Mar 31

includes taxes & fees

8/10 Very Good! (9,923 reviews)

Staff is very polite and friendly! Grant gardens and bus stops are very convenient. Beautiful views. Historical building and safe feeling.

Reviewed on Mar 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=9228)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $179

CA $248 total

Mar 24 - Mar 25

includes taxes & fees

9.4/10 Exceptional! (3,474 reviews)

Property is excellent and always clean

Reviewed on Mar 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&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 $141

CA $165 total

Mar 18 - Mar 19

includes taxes & fees

9/10 Wonderful! (3,882 reviews)

Parking was very expensive. Fitness areas were good. Room was ok.

Reviewed on Mar 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F03%2F2026&endDate=19%2F03%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=9228)

[See all 5,103 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F03%2F2026&endDate=10%2F03%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 featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.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)

![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.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 featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.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

![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)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**96%** 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)

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