Oak Park Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Top hotels in Oak Park

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 S$159 per night from 8 Dec to 9 Dec
S$159
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (8,182 reviews)
"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled"

Reviewed on 25 Nov,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 S$164 per night from 26 Dec to 27 Dec
S$164
includes taxes & fees
26 Dec - 27 Dec
8.6/10 Excellent! (3,551 reviews)
"Is very close to everything"

Reviewed on 23 Nov,2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 26 Dec to 27 Dec
S$152
includes taxes & fees
26 Dec - 27 Dec
8.4/10 Very Good! (3,272 reviews)
"It was a great experience"

Reviewed on 24 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
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 holiday package cost?
Explore the best of Oak Park from just . 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 holiday 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 holiday 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 holiday 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 cosy option is Stylish Luxe King Bed With Free Parkng Near Dt Oak Pk.
How far in advance should I book my Oak Park holiday?
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 travelling 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 holiday 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 holiday package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Oak Park holiday 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.

Popular places to visit

What to do in Oak Park

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.