Oak Park Holidays

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Top Oak Park Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
8/10 Very Good! (1,023 reviews)
Just too average for the price. If it was less money and same details, I’d have a little more appreciation for it.

Reviewed on 20 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Excellent service!!! Would highly recommend !! I have enjoyed this property many times and will return

Reviewed on 21 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (207 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 16 Mar 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (977 reviews)
The hotel was absolutely perfect for our quick weekend getaway. It was super comfortable, clean and safe. The staff was wonderful!

Reviewed on 19 May 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
EXCEPTIONAL SERVICE!!

Reviewed on 21 May 2024

Top hotels in Oak Park

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 HK$976 per night from 27 May to 28 May
HK$976
per night
27 May - 28 May
7.6/10 Good! (2,594 reviews)
"Very cozy"

Reviewed on 20 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is HK$1,160 per night from 28 May to 29 May
HK$1,160
per night
28 May - 29 May
7.6/10 Good! (6,775 reviews)
Live History!
"Incredible building with such nostalgia and grace (definitely ask to check out the Gold Room on the second floor). Huge lofted rooms, with GREAT A/C and comfy beds! Wonderful location next to gorgeous parks, beautiful fountains, and a short walk to the lake. Close to the CSO, Art Institute, and sooooo ..."

Reviewed on 20 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is HK$1,253 per night from 27 May to 28 May
HK$1,253
per night
27 May - 28 May
8.6/10 Excellent! (2,888 reviews)
"Staff at the front desk are really helpful and friendly"

Reviewed on 19 May 2024

River Hotel
See all 4,538 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 HK$3,711. 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 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

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

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
Image for McCormick Place

McCormick Place

4.5/5(36 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

What to do in Oak Park

Image for Skyline Lake Tour

Skyline Lake Tour

HK$294
Per adult
92% of travellers recommend
Skyline Lake Tour
Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

HK$1,473
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
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.