Oak Park Vacations from $336

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $665, price is now $336 per person
$336
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room

Reviewed on Jan 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $660, price is now $336 per person
$336
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast, Clean room, enjoyed the stay

Reviewed on Jan 9, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $756, price is now $423 per person
$423
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $874, price is now $492 per person
$492
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!

Reviewed on Jan 10, 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $642, price is now $370 per person
$370
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
We had a large room with an amazing view!

Reviewed on Jan 11, 2026

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

Discover the most popular places to visit in Oak Park

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

Michigan Avenue

4.5/5(332 reviews)

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
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in Oak Park

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$83
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Oak Park

Oak Park Hotel Deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 19 to Jan 20
$192 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (2,510 reviews)
Staff members were friendly and helpful. Great location walking distance and transportation options.

Reviewed on Jan 9, 2026

Hilton Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 18 to Jan 19
$105 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (3,677 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on Jan 7, 2026

Hilton Chicago/Magnificent Mile Suites
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Jan 30 to Jan 31
$103 total
Jan 30 - Jan 31
Total with taxes and fees
8.6/10 Excellent! (2,048 reviews)
Pedro and front office staff made our stay excellent. Return customer love the location, room quality and value overall. Room size and features make this our first choice in the city

Reviewed on Jan 7, 2026

Club Quarters Hotel Wacker at Michigan, Chicago
See all 5,145 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.

Find the Best Oak Park Vacation Packages

Oak Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
52,300
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Chicago Riverwalk, John G. Shedd Aquarium and Art Institute of Chicago

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oak Park vacation package cost?
Offering great value package deals from $336 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.

Explore a world of travel with Expedia

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