Oak Park Holidays

Book a Hotel + Flight or Car together to unlock savings

Oak Park Holiday

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
The price is NZ$466 per night from 15 Aug to 16 Aug
NZ$466
15 Aug - 16 Aug
includes taxes & fees
7.8/10 Good! (8,945 reviews)
"I love the location."

Reviewed on 11 Aug. 2025

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 NZ$385 per night from 21 Aug to 22 Aug
NZ$385
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (1,848 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on 11 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$320 per night from 25 Aug to 26 Aug
NZ$320
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (3,660 reviews)
"Great rooms, comfortable, walking distance to anywhere you’d want to go."

Reviewed on 10 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,972 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.

Discover the most popular places to visit in Oak Park

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Oak Park

River tour boat in Chicago

Architecture River Tour

NZ$69
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$75
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$67
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.