Oakton Holidays from AU$1,947

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Your Oakton Holiday

Make travel planning easy by reserving a holiday package to Oakton. Let us handle the small stuff, so you can concentrate on enjoying everything this neighbourhood can offer. When it's time to explore, your trip to Oakton has to include a visit to Rivers Casino and Arndt Park. Don't just think about it — take action! Secure your ultimate Oakton holiday with Expedia and travel your way.

Top Holiday Package Deals in Oakton

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was AU$3,379, price is now AU$1,947 per person
AU$1,947
per person
3 Dec - 8 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
8.8/10 Excellent! (1,663 reviews)
Convenient location to Grant Park.

Reviewed on 9 Oct 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$4,072, price is now AU$2,182 per person
AU$2,182
per person
3 Dec - 8 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!

Reviewed on 7 Oct 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,900, price is now AU$2,153 per person
AU$2,153
per person
3 Dec - 8 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Well laid out room. Clean, comfortable, friendly staff with an excellent location in River North.

Reviewed on 8 Oct 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$3,481, price is now AU$1,949 per person
AU$1,949
per person
3 Dec - 8 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
Awesome river north location, close to riverwalk, Michigan Ave, and lots of restaurants. Staff was helpful and friendly. Onsite restaurant was good. Wonderful large room, but there were a few items needing maintenance. Overall an excellent hotel.

Reviewed on 8 Oct 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$3,515, price is now AU$1,992 per person
AU$1,992
per person
3 Dec - 8 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
I wish that all the staff was more accommodating! some of them were some were not!

Reviewed on 6 Oct 2025

Our guide on where to stay in Oakton

Find the best Oakton areas and neighborhoods for the activities you enjoy most. Learn more about Oakton
Downtown Chicago featuring 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

Our pick of the best Oakton Hotel Deals

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 AU$227 per night from 2 Nov to 3 Nov
AU$227
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (9,333 reviews)
"Very clean"

Reviewed on 7 Oct 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$223 per night from 23 Oct to 24 Oct
AU$223
23 Oct - 24 Oct
includes taxes & fees
7.8/10 Good! (2,425 reviews)
"Excellent location, clean and good room partners"

Reviewed on 6 Oct 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$293 per night from 9 Nov to 10 Nov
AU$293
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"

Reviewed on 7 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,551 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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 AU$1,947. 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.

Discover the most popular places to visit in Oakton

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Activities

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.