Oakbrook Terrace Holidays

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Top hotels in Oakbrook Terrace

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$161
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (10,220 reviews)
"The hotel was just across for the Lollapalooza. The A/C wasn’t cool enough for me. My friend got locked in the bathroom when she used the older lock, the door knob looks older too,it took a while to maneuver that so almost call the front desk. Only 3pillows for the king size bed. No coffee maker, ..."

Reviewed on 7 Aug, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$231
9 Aug - 10 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
S$316
29 Aug - 30 Aug
includes taxes & fees
8.4/10 Very good! (2,373 reviews)
"Comfortable hotel in the airport. Staff is friendly and professional. Restaurant and bar were super congenial. Great place to stay on a quick trip to Chicago or on layover."

Reviewed on 6 Aug, 2026

Hilton Chicago O'Hare Airport
See all 4,834 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.

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.
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Loyola Medicine Oakbrook Terrace

If Loyola Medicine Oakbrook Terrace is what brings you to town, hopefully you'll have a chance to explore more of Oakbrook Terrace.
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What to do in Oakbrook Terrace

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Oakbrook Terrace

Frequently asked questions

How much does an Oakbrook Terrace holiday package cost?
You'll find cheap prices 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.

Explore a world of travel with Expedia

* 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.