Oak Park Vacations from $570

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,011, price is now $570 per person
$570
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
Great location to subways and river. Great experience.

Reviewed on Sep 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,157, price is now $702 per person
$702
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
The rooftop wss amazing and very friendly front desk. Even delivered birthday card and chocolates for the hubby.

Reviewed on Sep 28, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,363, price is now $842 per person
$842
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay

Reviewed on Sep 19, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,254, price is now $805 per person
$805
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Nice rooms and excellent service!

Reviewed on Sep 24, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $891, price is now $572 per person
$572
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe

Reviewed on Sep 27, 2025

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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

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
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
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

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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
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
$152 nightly
The price is $179 total per night from Oct 26 to Oct 27
$179 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on Sep 25, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $158 total per night from Oct 21 to Oct 22
$158 total
Oct 21 - Oct 22
Total with taxes and fees
7.8/10 Good! (2,387 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on Sep 24, 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $219 total per night from Oct 5 to Oct 6
$219 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (4,998 reviews)
"Lots of food options in the area. If you like to walk, you are close to many shops, Navy Pier, malls and the subway line. The hotel was nice, plenty of food included for breakfast and the happy hour is also nice. Rooms were spacious and everything worked nicely."

Reviewed on Sep 26, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,882 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 $570 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

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.