Oak Park Vacations from $355

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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.

The Latest Oak Park vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago - Glenview by IHG

Staybridge Suites Chicago - Glenview by IHG

3 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The room was very clean! I loved having an ice maker too! The staff was very helpful too. Highly recommend this hotel!

Reviewed on Aug 8, 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,156 reviews)
Room was nice and clean. Coffee in the lobby in the morning was great! The pool was underwhelming but seemed clean. The restaurant seemed understaffed. When we wanted to order a late lunch the bartender said he did not have a cook so we would have to wait. We decided to order a pizza from elsewhere since he was not very friendly about it.

Reviewed on Aug 11, 2025

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,517 reviews)
Located in a great location allowing to walk anywhere. Very clean and all the staff were very friendly upon arriving and throughout the stay!! Will for sure stay here again

Reviewed on Aug 10, 2025

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
My favorite part of my stay was the shower . I love the led lights in the shower . It’s so cool at night to watch the shower change colors .

Reviewed on Aug 11, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,631 reviews)
Great rooms, comfortable, walking distance to anywhere you’d want to go.

Reviewed on Aug 10, 2025

Don't see what you're looking for?
See all available trips from Chicago to Oak Park
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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

What to do in Oak Park

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
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

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Oak Park

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
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,943 reviews)
"The hotel room was quiet and clean, only a little old and something outdated but still functional (tv). The area is great to visit a lot of the Chicago attractions and staff was helpful. Would recommend!"

Reviewed on Aug 11, 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
$198 nightly
The price is $229 total per night from Sep 4 to Sep 5
$229 total
Sep 4 - Sep 5
Total includes taxes and fees
8.2/10 Very Good! (1,838 reviews)
"Great location. Very walkable and easy access to food and entertainment."

Reviewed on Aug 10, 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
$157 nightly
The price is $185 total per night from Aug 26 to Aug 27
$185 total
Aug 26 - Aug 27
Total includes taxes and fees
8.4/10 Very Good! (3,660 reviews)
"Great rooms, comfortable, walking distance to anywhere you’d want to go."

Reviewed on Aug 10, 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.

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Frequently asked questions

How much does an Oak Park vacation package cost?
Offering great value package deals from $355 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?
August, October and December are great times to look for cheap Oak Park vacation packages. Opting to travel in less busy months means you can generally find lower prices on accommodations and flights.
How many days is enough for Oak Park?
To get the most out of an Oak Park vacation, we suggest booking for 2 days. Divide your time between discovering Ernest Hemingway Museum and House, Unity Temple and other major sights, as well as exploring neighborhoods like United Center and Illinois Medical District. If you've got some spare time, add a day trip to your Oak Park vacation itinerary.
Is it worth booking a vacation package to Oak Park?
Known for its history, culture and a host of other highlights, you can be certain Oak Park is a good vacation destination. Some of the top attractions to put on your itinerary? Don't miss Ernest Hemingway Museum and House and Unity Temple during your Oak Park vacation.
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. Pick your travel dates: The things you want to do in Oak Park and your preferred season can help you decide when to go.
  2. Budget wisely: As well as the price of your hotel, you'll need to factor in other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that may come up during your trip to Oak Park.
  3. Explore Oak Park using Expedia's trip planning tool: Gain insights into the leading attractions and best properties for your trip to Oak Park. You can also save your favorite locations, collaborate with friends and family and organize all your plans in one place.
  4. Work out your trip length: Consider how long you want to spend discovering Oak Park. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose an Oak Park vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Take a look at our travel guide to find some fun things to do in Oak Park. Book tickets or make reservations as soon as you can to save time and avoid the hassle of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Oak Park vacation packages?
Jet off on your dream getaway to Oak Park with help from our Book Now, Pay Later vacations. No need to save like crazy or wait until your next paycheck — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.