Title: Oak Park Vacation Packages & Trips 2026 from CA $1,016 | 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

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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.

![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 $1,016

per person

Mar 3 - Mar 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (317 reviews)

Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!

Reviewed on Jan 10, 2026

![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 $1,143

per person

Mar 3 - Mar 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.

Reviewed on Jan 12, 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 $1,880

per person

Mar 3 - Mar 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Yes didn’t know you get free breakfast

Reviewed on Jan 4, 2026

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Palmer House a Hilton Hotel

Downtown Chicago

CA $1,153

per person

Mar 3 - Mar 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very Good! (2,059 reviews)

Very close to Arts Institute and CSO. Helpful staff. Very good SPA + fitness + pool.

Reviewed on Jan 17, 2026

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $1,285

per person

Mar 3 - Mar 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,264 reviews)

Nice newer hotel with lots of options. Rooms are a bit industrial but fine, nothing super luxurious but adequate.

Reviewed on Jan 16, 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/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 $126

CA $148 total

Jan 19 - Jan 20

includes taxes & fees

8/10 Very Good! (9,771 reviews)

Front desk was very professional and the room was very tidy, including the bathroom. Staff allowed us to check in early (no fee, if room is cleaned and available, prior to standard check in time.). Overall, not a bad selection based on location and proximity of all the sites to see. Quiet side of ...

Reviewed on Jan 14, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=9228)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $181

CA $254 total

Feb 1 - Feb 2

includes taxes & fees

8.4/10 Very Good! (2,529 reviews)

Nice size rooms, accommodating check in help, and great location

Reviewed on Jan 12, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true&regionId=9228)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_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 $112

CA $131 total

Jan 25 - Jan 26

includes taxes & fees

8.8/10 Excellent! (3,708 reviews)

Very nice, check-in and check out fast and efficient. Staff very helpful and welcoming

Reviewed on Jan 14, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=9228)

[See all 5,145 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F01%2F2026&endDate=20%2F01%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://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

![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)

![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

CA $49

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.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

**100%** 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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