Oak Park Vacations

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Find the Best Oak Park Vacation Packages

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 NT$7,533 per night from Sep 7 to Sep 8
NT$7,533
NT$8,843 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (8,971 reviews)
"Great location! But too old hotel with rooms with older amenities."

Reviewed on 2025/8/12

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 NT$5,188 per night from Sep 4 to Sep 5
NT$5,188
NT$6,838 total
Sep 4 - Sep 5
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 2025/8/11

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 NT$4,043 per night from Sep 2 to Sep 3
NT$4,043
NT$4,746 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Very classy safe snd clean"

Reviewed on 2025/8/12

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 featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Frequently asked questions

How much does an Oak Park vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation 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 vacation in order to discover everything that makes this place unique. Wander around key neighborhoods, 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 vacation package to Oak Park?
During your Oak Park vacation, 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 vacation as a package?
You can enjoy significant savings on your next Oak Park getaway by booking a personalized vacation 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 vacation 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, favorite 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 accommodations and airfare: After you've settled on your dates and duration, lock in the right Oak Park vacation package for you.

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