Oak Park Vacations from $557

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Your Oak Park Vacation

There's no better way to escape than with one of our vacation packages to Oak Park. The chic vibe and rich history are among the compelling reasons you'll want to visit this fascinating city. United Center, Brookfield Zoo and Anna and Frederick Douglass Park are just a few of the many attractions worth visiting during your trip to Oak Park. Stop dreaming and start doing. Explore the range of options on Expedia today and finally put your Oak Park vacation plans in motion!

The Latest Oak Park Vacation Packages

Prices and availability subject to change. Additional terms may apply.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 15 - Jun 18
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The staff are thoughtful and provide the best service. While I was there, I was already planning to come back and stay there again!

Reviewed on Apr 24, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Amazing. Definitely coming back!

Reviewed on Apr 20, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (650 reviews)
Great customer service

Reviewed on Apr 21, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
The location was great, rooms were cozy, and staff was friendly! Highly recommend!

Reviewed on Apr 25, 2024

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

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 $127 per night from Apr 28 to Apr 29
$127
$149 total
includes taxes & fees
Apr 28 - Apr 29
7.6/10 Good! (6,585 reviews)
"A great older hotel. Very happy with my stay here."

Reviewed on Apr 23, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $139 per night from Apr 28 to Apr 29
$139
$163 total
includes taxes & fees
Apr 28 - Apr 29
8.6/10 Excellent! (2,802 reviews)
"It was nice to be able to see the river view. Parking fee was also cheaper."

Reviewed on Apr 23, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $160 per night from Apr 28 to Apr 29
$160
$188 total
includes taxes & fees
Apr 28 - Apr 29
8.2/10 Very Good! (1,859 reviews)
"A beautiful hotel n vibe I had a wonderful stay! We loved the peek a boo showers!"

Reviewed on Apr 25, 2024

Eurostars Magnificent Mile
See all 4,540 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Oak Park vacation package cost?
Explore the best of Oak Park from just $557. Choose from a wonderful selection of flights, rental cars and hotels to suit every budget. Land even better deals when you add a couple of activities or tours to your vacation package.
How do I get a cheap travel package to Oak Park?
Bundle your hotel and flight bookings, throw in extras such as tours, and save with an Oak Park vacation package. You won’t just land amazing discounts on your escape — you’ll have lots of choice too. When you book with Expedia, you can select from more than 550 partner airlines and 1,000,000 properties around the globe. Your next big adventure starts right here, right now!
Where should I stay in Oak Park?
With interesting attractions like Frank Lloyd Wright Historic District and Ernest Hemingway Museum and House in this area, try to find a hotel situated near either one. Concordia University Chicago is another sight in Oak Park that draws in the crowds.
What are the top hotels in Oak Park?
Get your vacation off to a fantastic start by booking a stay at Elegantly Decorated Spacious 4 Bedroom. It’s one of most popular hotels in Oak Park. Another cozy option is Stylish Luxe King Bed With Free Parkng Near Dt Oak Pk.
How far in advance should I book my Oak Park vacation?
While prices fluctuate, we generally suggest reserving your seat as soon as possible. Most international airfares can be found on Expedia up to a year in advance. If you’re booking last minute, you might still get lucky. Cheap tickets to Oak Park occasionally appear just weeks before departure.
What does an Expedia Oak Park travel package include?
Rental cars, hotels and flights, or any combination of them — it’s your choice. Whether you’re exploring Oak Park with the family or traveling by yourself, there’s a package to fit every style and budget. Once you’ve made your booking, why not add on some tours or activities?
What should I know before booking an Oak Park travel package?
You can save big by combining your airfares, hotels and rental cars. Once you’ve created your package, add on fun stuff like activities or tours. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with an Oak Park Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you sure can! Simply select the airline you want and craft the perfect Oak Park trip.
If I'm not able to travel, can I cancel my Oak Park vacation package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Oak Park vacation package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, airline or hotel may impose a fee. Need more information? Have a look at our Customer Service Portal. We’ll help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Oak Park

Image for Wrigley Field

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
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

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
Image for Navy Pier

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

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$75
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Oak Park

Other vacations you might like

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