Oakton Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Oakton

Find the best Oakton areas and neighborhoods for the activities you enjoy most. Learn more about Oakton
Downtown Chicago which includes a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Oakton

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 20 Jan to 21 Jan
S$247
20 Jan - 21 Jan
includes taxes & fees
8.4/10 Very Good! (2,501 reviews)
Everything was amazing abt my stay

Reviewed on 7 Jan, 2026

Hilton Chicago
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 S$135 per night from 25 Jan to 26 Jan
S$135
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (3,678 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on 7 Jan, 2026

Hilton Chicago/Magnificent Mile Suites
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$123 per night from 26 Jan to 27 Jan
S$123
26 Jan - 27 Jan
includes taxes & fees
8.6/10 Excellent! (2,051 reviews)
Great location & everyone was very helpful. Needed a fridge for medication & they set us up in a room with one.

Reviewed on 8 Jan, 2026

Club Quarters Hotel Wacker at Michigan, Chicago
See all 4,825 properties in Oakton
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 Oakton holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Oakton from just . And the more you bundle, the more dollars you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to Oakton?
Imagine all the fun things you could do in Oakton with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and extras into an Oakton holiday package. You have plenty of choice when you book with Expedia too. In fact, you can take your pick of more than 550 air carriers and 1,000,000 properties around the globe. Whether you're taking off with the entire family or adventuring alone, organising a getaway to Oakton is better with a package.
Where should I stay in Oakton?
With interesting attractions like Holy Family Hospital and Holy Family in this area, look for a hotel positioned near either of them. Arndt Park is another sight in Oakton that people flock to.
How far in advance should I book my Oakton holiday?
You'll be rewarded with the biggest variety and the lowest prices by booking your trip to Oakton nice and early. Air carriers tend to release flight tickets around 12 months prior to departure, so start locking things in as soon as you can. That being said, Expedia is dedicated to giving you the best bargains around, so it's always a good time to book your dream holiday!
What does an Expedia Oakton travel package include?
From hotels and airfares to car rentals, Expedia can help you shape an Oakton package that's right for you. Holidaying for a week or two? Give some thought to a rental car, hotel and flight bundle. If you're taking a short break, a hotel and flight deal could be what you're after. Tours and activities can be added after you've booked. Our packages make it easy to save and plan.
What should I know before booking an Oakton travel package?
So many places to go, so many things to experience. With a package, you'll be able to check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with an Oakton Expedia holiday package?
With a holiday package, you're in charge. Whether you'd like to fly to Oakton in coach or first class, simply select from the available airline options. Expedia has access to more than 550 airline partners around the world.
If I'm not able to travel, can I cancel my Oakton holiday package?
Because we know life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your Oakton holiday package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
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
Soldier Field showing a city, modern architecture and a skyscraper

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$57
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago

* 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.