Oak Park Vacations from ￥346,298

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The Latest Oak Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Jul 5 - Jul 11
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (205 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Jul 5 - Jul 11
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Great place to stay, easy access to Riverwalk, Mag Mile and lots of architectural wonders. Staff were extremely helpful, special shoutout to concierges Mary and Edward for all their help!

Reviewed on May 13, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul 30 - Aug 3
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Just comparing it to always staying at the Peninsula. The 5 star service wasn’t near as good and it was just stuffy. The workers weren’t near as nice and welcoming.

Reviewed on May 13, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Jul 30 - Aug 3
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
I was pleasantly surprised to find artwork displayed throughout the property, including my favorite Kehinde Wiley.

Reviewed on May 12, 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
Jul 5 - Jul 11
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,009 reviews)
Everyone was so nice. The staff was lovely and I will definitely book my room there again.

Reviewed on May 11, 2024

Oak Park Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥17,915 per night from May 27 to May 28
￥17,915
per night
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Nice view. Great location. I just bounced in and out for a concert but I would totally stay here again."

Reviewed on May 12, 2024

Warwick Allerton - Chicago
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 ￥24,260 per night from May 14 to May 15
￥24,260
per night
May 14 - May 15
7.6/10 Good! (6,713 reviews)
"The Congress is a short wall to the Symphony, and the art museum. It's an old hotel but clean and everything worked. Mattresses were a little too firm for me."

Reviewed on May 11, 2024

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥30,377 per night from May 27 to May 28
￥30,377
per night
May 27 - May 28
8.6/10 Excellent! (1,007 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 4,608 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.

Frequently asked questions

How much does an Oak Park vacation package cost?
Explore the best of Oak Park from just ￥346,298. 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 Six Flags Great America

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Oak Park

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

￥27,764
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
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.