Vacations to Oak Park

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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.

Top Oak Park Vacation Deals

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 7 - Jun. 10
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on Apr. 14, 2024

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. 2 - Jun. 5
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 1 - Jul. 6
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on Apr. 15, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 2 - Jun. 5
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Every single person working at this facility was extremely polite and welcoming. I’ve stayed in so many hotels across the world and I have to say this was the best experience I’ve ever had staying at a hotel. Ordered food at 3am and it was fantastic. My cloths got folded in the short period of time my wife and I left the room and came back to a spotless room. Overall amazing experience. Will be staying here every time I come to Chicago.

Reviewed on Apr. 16, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 5 - Jul. 8
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
YOGA AND POOL AND ELEGANT LUNCH AREA PLUS LOVE MY SUITE !!!!

Reviewed on Apr. 17, 2024

Prices and availability subject to change. Additional terms may apply.

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 CA $157 per night from Apr. 21 to Apr. 22
CA $157
CA $185 total
includes taxes & fees
Apr 21 - Apr 22
7.6/10 Good! (6,559 reviews)
"The only thing I didn’t like was that when we got there we wait about 20 minutes for someone to help us check in and no matter where you parked you have to pay"

Reviewed on Apr. 19, 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 CA $169 per night from Apr. 21 to Apr. 22
CA $169
CA $198 total
includes taxes & fees
Apr 21 - Apr 22
8.6/10 Excellent! (2,786 reviews)
"Great location for downtown access"

Reviewed on Apr. 18, 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 CA $207 per night from Apr. 23 to Apr. 24
CA $207
CA $243 total
includes taxes & fees
Apr 23 - Apr 24
8.2/10 Very Good! (1,846 reviews)
Great hotel
"Great location in central Chicago. Staff were very polite and courteous. Large room and shower in particular was fantastic."

Reviewed on Apr. 17, 2024

Eurostars Magnificent Mile
See all 4,555 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

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Family Vacations

Frequently asked questions

How much does an Oak Park vacation package cost?
Explore the best of Oak Park from just CA $708. 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(158 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(141 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(459 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

CA $73
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $102
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Oak Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.