Oakbrook Terrace Holidays from AU$2,121

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The Latest Oakbrook Terrace Holiday 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
Price was AU$3,292, price is now AU$2,121 per person
AU$2,121
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
Very clean. Had everything that we needed

Reviewed on 10 Nov 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was AU$4,430, price is now AU$2,847 per person
AU$2,847
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on 10 Nov 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was AU$3,634, price is now AU$2,346 per person
AU$2,346
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$4,057, price is now AU$2,628 per person
AU$2,628
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨

Reviewed on 9 Nov 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was AU$3,374, price is now AU$2,201 per person
AU$2,201
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,181 reviews)
A little dated and in need of bathroom remodeling, but clean and comfortable.

Reviewed on 10 Nov 2026

Oakbrook Terrace Holiday

Oakbrook Terrace Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
2,200
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC

Our pick of the best Oakbrook Terrace 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$199 per night from 22 Nov to 23 Nov
AU$199
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (10,163 reviews)
"Love that this is a classic Chicago downtown hotel experience! The lobby area is such a throwback to a different era in Chicago, which is cool. The rooms (we were in 933) are in desperate need of an upgrade by whatever parent company owns this hotel. The bathroom was severely outdated with a bathroom ..."

Reviewed on 10 Nov 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 22 Nov to 23 Nov
AU$196
22 Nov - 23 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 10 Dec to 11 Dec
AU$182
10 Dec - 11 Dec
includes taxes & fees
8.8/10 Excellent! (5,613 reviews)
"Room was cleaned and nicely kept up. Convenient location and nice view of the river."

Reviewed on 10 Nov 2026

River Hotel
See all 4,774 properties in Oakbrook Terrace
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.
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Stay near popular Oakbrook Terrace attractions

Drury Lane Theater

8.8/10 (93 reviews)
This historic theatre captivates with Broadway-caliber musicals and intimate performances in an elegant setting. Enhance your evening with pre-show dining at Lucille Restaurant, known for its champagne brunch.
See properties

What to do in Oakbrook Terrace

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Oakbrook Terrace

Frequently asked questions

How much does an Oakbrook Terrace holiday package cost?
You'll find cheap prices from AU$2,121 on Expedia for your Oakbrook Terrace getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Oakbrook Terrace costs.
What are the cheapest months to go to Oakbrook Terrace?
You can typically find lower prices and better availability in December, January and February. Explore our cheap Oakbrook Terrace holiday packages and you could score some great off-season deals.
How many days is enough for Oakbrook Terrace?
The ideal length of your Oakbrook Terrace holiday depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to hit all the top sights and discover some hidden gems along the way.
How to find the best Oakbrook Terrace package deals?
Landing a cheap Oakbrook Terrace package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can personalise your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Oakbrook Terrace package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakbrook Terrace holiday as a package?
You can enjoy significant savings on your next Oakbrook Terrace getaway by booking a customised holiday package. Check the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Oakbrook Terrace?
If you have your Oakbrook Terrace travel dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Oakbrook Terrace?

  1. Choose when to travel: Check your diary and get packing. Your favourite season and the type of activities available will also help you decide when to holiday in Oakbrook Terrace.
  2. Budget wisely: Besides the cost of your accommodation, you should consider other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Oakbrook Terrace.
  3. Decide how long to go for: Now that you know more about Oakbrook Terrace, you can work out the perfect length of your holiday. Pull together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodation and airfare: Once you've nailed down your travel dates and duration, book the right Oakbrook Terrace holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.