Oakbrook Terrace Vacations from $386

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The Latest Oakbrook Terrace vacation packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $623, price is now $386 per person
$386
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $925, price is now $530 per person
$530
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room Clean bathroom Friendly staff

Reviewed on Jan 1, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,006, price is now $605 per person
$605
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.

Reviewed on Dec 31, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $671, price is now $408 per person
$408
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Had a great dinner at Fora before a very short walk to the new years eve event we were headed to and then came back for a great night's sleep in a very comfortable room! All the staff we interacted with were great!

Reviewed on Jan 1, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $633, price is now $397 per person
$397
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Everything was great!

Reviewed on Dec 29, 2025

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Discover the most popular places to visit in Oakbrook Terrace

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy 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
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Oakbrook Terrace

River tour boat in Chicago

Architecture River Tour

$44
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$83
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Oakbrook Terrace

Oakbrook Terrace Hotel Deals

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
$89 nightly
The price is $105 total per night from Jan 11 to Jan 12
$105 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (3,613 reviews)
Clean room , great location.

Reviewed on Dec 30, 2025

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 11 to Jan 12
$192 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (2,445 reviews)
Best option for us while attending an event at McCormick place, with ability to park in public parking that is cheaper than the hotel parking!

Reviewed on Dec 30, 2025

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Jan 11 to Jan 12
$192 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (2,208 reviews)
We loved the restaurant staff and options. Mrs. Rose and Tony.

Reviewed on Jan 2, 2026

Palmer House a Hilton Hotel
See all 5,080 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.

Find the Best Oakbrook Terrace Vacation Packages

Oakbrook Terrace Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
2,200
Max Temp Winter
30ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does an Oakbrook Terrace vacation package cost?
You'll find cheap prices from $386 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 vacation to Oakbrook Terrace costs.
What are the cheapest months to go to Oakbrook Terrace?
November, December and January are great times to look for cheap Oakbrook Terrace vacation packages. Choosing to travel in less busy periods means you'll typically find better prices on flights and hotels.
How many days is enough for Oakbrook Terrace?
The ideal length of your Oakbrook Terrace vacation depends on what you'd like to do. Usually, a few days to a week will give you enough time to visit all the leading sights and explore some hidden treasures 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 personalize 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 traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakbrook Terrace vacation as a package?
You can enjoy significant savings on your next Oakbrook Terrace getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Oakbrook Terrace vacation packages?
Jet off on your dream escape to Oakbrook Terrace with help from our Book Now, Pay Later vacations. There's no need to save up or wait for your next paycheck — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snap up travel deals while they last.

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.