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, Brookfield Zoo and Portage Park 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.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was CA $956, price is now CA $715 per person
CA $715
per person
Sep 11 - Sep 13
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,010 reviews)
The hotel staff was great! Very friendly and accommodating. The bar staff at the casino was not great. Granted a new bartender was just coming on shift, but no one else would serve any of the guests. 4 bartenders behind the bar and 10+ guests waiting on service.....it just didn't make any since. Overall I would stay there again, just probably would not go back to the casino bar. The lounge looked nice but nobody was working that area.

Reviewed on Jul 21, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $3,537, price is now CA $2,414 per person
CA $2,414
per person
Sep 27 - Oct 3
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,150 reviews)

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was CA $2,724, price is now CA $1,962 per person
CA $1,962
per person
Sep 27 - Oct 3
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,392 reviews)
The hotel is nice and the rooms are generally good, but they are not keeping up with maintenance. The plastic backboard of the bed was worn and ripped (and gross looking), and the AC was very intense and uncomfortable. Carpet and walls in halls need repair. In short, the hotel is not worth the cost.

Reviewed on Jul 20, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $4,660, price is now CA $3,460 per person
CA $3,460
per person
Sep 27 - Oct 3
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,318, price is now CA $982 per person
CA $982
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (501 reviews)

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Oak Park Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $267 per night from Aug 6 to Aug 7
CA $267
CA $304 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (2,878 reviews)
"My Fourth of July weekend stay was nothing short of extraordinary. From the moment I arrived, I was welcomed with an incredible level of hospitality, professionalism, and attention to detail that immediately set the tone for an unforgettable experience. Every aspect of my stay exceeded my expectations, ..."

Reviewed on Jul 22, 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Aug 10 to Aug 11
CA $255
CA $304 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very good! (1,805 reviews)
"Still waiting to receive the $150 deposit they charged upon arrival - it's been well over a week and has yet to come back to my account."

Reviewed on Jul 22, 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Jul 26 to Jul 27
CA $281
CA $334 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,933 reviews)
"The king room with a view of the lake was quite spacious and perfect for our needs. The only downside was parking was quite expensive at $86/night."

Reviewed on Jul 22, 2026

The Wade
See all 4,848 properties in Oak Park
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.
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Stay near popular Oak Park attractions

A stained glass window with geometric patterns and multiple colors.
Photo by Krystalvation
Open Photo by Krystalvation

Frank Lloyd Wright Historic District

9.2/10 (25 reviews)
Visit the birthplace of modern architecture to explore the world's largest collections of homes and buildings designed by Frank Lloyd Wright.
See properties

What to do in Oak Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Oak Park

Frequently asked questions

How much does an Oak Park vacation package cost?
You'll find cheap prices from CA $715 on Expedia for your Oak Park break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oak Park costs.
What are the cheapest months to go to Oak Park?
If you're hoping to snag a cheap Oak Park vacation package, consider planning a trip in January, February and March. You'll generally find better prices on accommodations and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Oak Park?
We'd recommend booking an Oak Park vacation for around 2 days. This gives you time to check off top sights including Portage Park and Humboldt Park, as well as check out neighbourhoods like Illinois Medical District and West Town. You could even fit in one or two day trips beyond Oak Park.
Is it worth booking a vacation package to Oak Park?
Whether you're planning to explore attractions such as Unity Temple and Madison Street Theatre, or eager to experience its terrific history and culture, an Oak Park vacation will leave you with lasting memories. Book your trip with Expedia and find out why Oak Park is such a good vacation destination.
How to find the best Oak Park package deals?
Finding a cheap Oak Park package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Oak Park package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Oak Park vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can personalize your Oak Park escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Oak Park?
If you're planning a spur-of-the-moment Oak Park adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Oak Park?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Oak Park.
  2. Budget wisely: On top of the price of your stay, you should factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Oak Park.
  3. Decide how long to go away for: Now that you're more familiar with Oak Park, you can figure out the right length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find an Oak Park vacation package that brings all your bookings together.

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