Oak Park Holidays

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Your Oak Park Holiday

There's no better way to embark on an adventure than with one of our holiday packages to Oak Park. The chic vibe and rich history are just two of the many reasons to stay in this interesting city. Fill your days with visits to United Centre, Brookfield Zoo and Anna and Frederick Douglass Park, some of the things you shouldn't miss during your trip to Oak Park. Don't delay your visit to this destination any longer. Your dream Oak Park holiday is only a few clicks away with Expedia.

Oak Park Holiday

Oak Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
52,300
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago

Our pick of the best Oak Park Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (8,974 reviews)
"Great location! Rooms are newly renovated and nice."

Reviewed on 5 Aug. 2025

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Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$353 per night from 22 Aug to 23 Aug
AU$353
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,820 reviews)
"Beautiful gilded age feel. Long wait for elevators is my only complaint"

Reviewed on 3 Aug. 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is AU$265 per night from 24 Aug to 25 Aug
AU$265
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,336 reviews)
"Thanks beautiful place"

Reviewed on 3 Aug. 2025

Crowne Plaza Chicago West Loop by IHG
See all 5,079 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Oak Park

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Oak Park

River tour boat in Chicago

Architecture River Tour

AU$64
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

AU$46
per adult
92% of travellers recommend
Skyline Lake Tour
Chicago White Sox Baseball Game at Guaranteed Rate Field

Chicago White Sox Baseball Game at Guaranteed Rate Field

AU$31
per adult
Chicago White Sox Baseball Game at Guaranteed Rate Field
See all activities in Oak Park

Frequently asked questions

How much does an Oak Park holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Oak Park costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oak Park?
You can usually find reduced prices and greater availability in January, February and March. Take a look at our cheap Oak Park holiday packages and you could score some great off-season discounts.
How many days is enough for Oak Park?
Dedicate at least 2 days for your Oak Park holiday in order to discover everything that makes this place unique. Wander around key neighbourhoods, including Illinois Medical District and West Town. Then check out major sights like Unity Temple and Oak Park Conservatory. With a clever itinerary, you'll be kept busy with room for some me-time too. Want to go beyond Oak Park? Consider squeezing in an excursion or two.
Is it worth booking a holiday package to Oak Park?
During your Oak Park holiday, you can look forward to enjoying some excellent history and culture. Leave enough room in your schedule to visit leading attractions like Unity Temple and Madison Street Theatre.
How to find the best Oak Park package deals?
Begin your search for an Oak Park package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Oak Park package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oak Park escape off to a flying start.
Is it cheaper to book an Oak Park holiday as a package?
You can enjoy significant savings on your next Oak Park getaway by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Oak Park?
If you're considering a spontaneous Oak Park getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Oak Park?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Oak Park.
  2. Set your budget: Consider costs such as food, flights and transportation when working out how much to save for your trip to Oak Park. Then, select a property that works with your budget, whether that's a low-cost stay or a swankier retreat.
  3. Decide how long to go away for: Now that you know more about Oak Park, you can figure out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your accommodation and airfare: After you've settled on your dates and duration, lock in the right Oak Park holiday package for you.

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