Oak Park Holidays from £1,087

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Your Oak Park Holiday

Lock in an Oak Park holiday package and get ready for an awesome adventure. Renowned for its chic vibe and rich history, there's loads to keep you on the go in this fascinating city. You'll want to take in the sights during your trip to Oak Park. Find time for famous attractions like United Centre, Brookfield Zoo and Anna and Frederick Douglass Park. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Oak Park holiday is a breeze with Expedia.

The Latest Oak Park Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
12 Jul - 19 Jul
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,171 reviews)
Little disappointed there was no free breakfast

Reviewed on 1 May 2024

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

3.5 out of 5
Downtown Chicago
per person
12 Jul - 19 Jul
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
The location was really close to the places I wanted to see while I was in town. The staff was really accommodating and helpful. The restaurant connected to hote was really good and convenient before we had to drive back to airport. Even though i didn’t want to pay for $60 valet, it was really easy when I needed the car to take a drive. I also didn’t like the rooms windows, seems they are single pane and you get a lot of outdoor noise at night.

Reviewed on 1 May 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
12 Jul - 19 Jul
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
Overall experience was fantastic. Definitely the best choice available in Chicago

Reviewed on 29 Apr 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
12 Jul - 19 Jul
Return flight included
London (LON) 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 16 Mar 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
12 Jul - 19 Jul
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (663 reviews)
It's really a beautiful looking Hotel and the rooms are very nice and clean. they play loud obnoxious music in the Lobby which I guess a teenager would probably like. Read the fine print. they have a $41 a day "Destination fee" which gets you a cup of coffee from 6am-9am(Not great coffee and not always hot) and bottles of water. A welcome drink (only first day) if you use their mix which they add a shot)They say there is a shuttle service (first come first serve) they don't tell you that it is only on the weekend until you ask about it Monday Morning. $41 dollars a day for that? This needs to be addressed. I feel it is an excuse to get more money out of you. I stayed three nights and was hit for $123. My fault I didn't see the charge that was down at the end of the page. A lot of street noise but Hotel was quiet by itself and the Maids were so friendly and sweet.

Reviewed on 30 Apr 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
12 Jul - 19 Jul
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (3,477 reviews)
The website needs clear, easy to find information about parking.

Reviewed on 5 May 2024

Oak Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
52,300
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago

Our pick of the best Oak Park Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (6,663 reviews)
Good stay
"Had a remolded/upgraded room. View of the lake it was nice and clean."

Reviewed on 5 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service and a fitness centre. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,851 reviews)
"Clean building and room. Excellent staff. Walking distance to everything i needed to see and do."

Reviewed on 5 May 2024

River Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this family-friendly hotel in Chicago. Enjoy a 24-hour fitness centre, valet parking and in-room massages. Our guests praise the helpful staff and the ...
7.6/10 Good! (2,547 reviews)
"Bartenders were the best"

Reviewed on 3 May 2024

Warwick Allerton - Chicago
See all 4,534 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Oak Park holiday with Expedia?
Choose Expedia to organise your next adventure easily and all in the same place. Our top tip for bagging the best deal on an Oak Park getaway? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in a couple of fun tours and activities. Many bookings also come with flexible cancellation policies, so there’s no need to panic if you have to switch up your travel agenda. Round-the-clock help with making changes to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Oak Park?
Oak Park is at its busiest in January, March and June. If you’re hoping for a more relaxed holiday, visit in August, October and December. With daytime average temperatures of -3ºC, January is the coolest period in Oak Park. The warmest time of year is July, when you can expect averages of 23ºC throughout the day. Whatever the temperature, you’ll discover plenty of things to keep you busy here.
What is the top hotel for my holiday in Oak Park?
LondonHouse Chicago, Curio Collection by Hilton sets the scene for a memorable trip to Oak Park, offering all the conveniences you need.
How do I get a cheap holiday to Oak Park?
Browse and lock in everything all in one place with our Oak Park holidays. You’ll discover bargains on hotels, flights and more that’ll keep your hip pocket happy and your adventurous spirit busy. And, with more than 400 partner airlines and 321,000 properties globally to pick from, you have countless opportunities to mix and match however you please. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Oak Park holiday?
Make sure your next holiday in Oak Park is an unforgettable one by stopping by its top attractions. McCormick Place, Wrigley Field, Millennium Park and Willis Tower are among the things to put on your itinerary while you’re in the city.
What is the best area to stay in when on holiday in Oak Park?
Oak Park has many fascinating places to see, like Ernest Hemingway Museum and House. Stay somewhere nearby and make sightseeing a breeze.
Do I need a visa for my Oak Park holiday?
Visa requirements for Oak Park vary depending on your nationality and purpose of your visit. Be sure to check official government websites to determine if you need a visa for your holiday. This is also a good place to find the most up-to-date information, including details about application procedures or supporting documentation that may be necessary. Research your visa requirements well ahead of time to ensure a travel experience that’s hassle free. Also make sure your passport has at least six months validity from your return date.
What should I wear on my Oak Park holiday?
Consider the activities planned during your Oak Park trip and create a travel wardrobe that you can mix and match. For fashion inspiration or information on any dress codes, look up style blogs or relevant social media accounts. Pack with confidence by monitoring the weather conditions in Oak Park. July brings the warmest temperatures, with daytime averages of 23ºC, while January days average -3ºC, making it the coolest time of year.
What does an Expedia Oak Park holiday include?
Much of that depends on you. Simply choose from a variety of Oak Park packages, such as a hire car, flight and hotel. You can also book a flight with a hotel, or a flight with a car hire. Once you’ve made your booking, add the fun stuff like experiences and tours. Whatever your dream Oak Park getaway looks like, you’ll save! Explore an excellent range of property types and choose one that fits your group size. The most sought-after holiday rentals here are apartments and private holiday homes. With Expedia, you can easily design your Oak Park retreat the way you like.
Does Expedia offer Book Now, Pay Later Oak Park holidays?
We sure do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna’s convenient monthly instalment plans. If paying across multiple instalments works for you, choose this option at checkout.
  • No-deposit holidays: When you want to jump on an unbeatable deal but your budget doesn’t quite cover it yet, Klarna’s no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your escape.

Can I choose my airline with an Oak Park Expedia holiday?
Yes — that’s the beauty of an Expedia package. You get to decide. We have access to more than 400 airline partners around the world, so you have options galore when planning your Oak Park adventure.

Discover the most popular places to visit in Oak Park

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 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
Image for Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Unmissable things to do in Oak Park

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

£182
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

£43
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
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. Flight-inclusive packages are ATOL protected.