Oak Park Holidays from £973

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    Packages with flights are ATOL protected

Your Oak Park Holiday

With one of our holiday 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 Centre, 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 holiday is a walk in the park with Expedia.

Top Oak Park Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Sept - 13 Sept
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Comfortable beds and nice breakfast. Close to parking. Recommend.

Reviewed on 19 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Superior customer service!

Reviewed on 19 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
The location of the hotel was perfect. A lot of restaurants and tourist attractions were walking distance and majority of the public transportation was near by as well

Reviewed on 19 Jul 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Plenty of options to eat at Navy Pier and parking was very close using the East garage. Hotel used texting feature which was great for any questions or assistance. Great view of the water from our room. Great location to access boat cruises and fireworks

Reviewed on 18 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

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

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 £153 per night from 25 Jul to 26 Jul
£153
25 Jul - 26 Jul
includes taxes & fees
7.8/10 Good! (8,856 reviews)
"I loved everything about my stay at the congress plaza. Were the rooms updated no. But it had it charm. I am in love with the designs of the 1920. The staff were extremely accommodating. They did not even charge me for late check out. I will be staying here again."

Reviewed on 16 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £259 per night from 19 Aug to 20 Aug
£259
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (2,066 reviews)
"The pool was amazing!!"

Reviewed on 19 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £128 per night from 10 Aug to 11 Aug
£128
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,484 reviews)
"Overall good experience"

Reviewed on 19 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,856 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

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Oak Park

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Oak Park

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.

* 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.