Oakbrook Terrace Vacations from $155

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The Latest Oakbrook Terrace vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $283, price is now $155 per person
$155
per person
Feb 28 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room. Extremely friendly staff and beautiful atmosphere.

Reviewed on Jan 20, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,572, price is now $892 per person
$892
per person
Mar 22 - Mar 27
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel

Reviewed on Jan 20, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,057, price is now $604 per person
$604
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on Jan 8, 2026

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Save 100% on your flight
Price was $604, price is now $376 per person
$376
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars.

Reviewed on Jan 12, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,160, price is now $726 per person
$726
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast

Reviewed on Jan 4, 2026

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Discover the most popular places to visit in Oakbrook Terrace

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(332 reviews)

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
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in Oakbrook Terrace

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
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
Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

$67
per adult
Chicago Blackhawks Ice Hockey Game at United Center
See all activities in Oakbrook Terrace

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
$87 nightly
The price is $102 total per night from Jan 24 to Jan 25
$102 total
Jan 24 - Jan 25
Total with taxes and fees
8/10 Very Good! (9,790 reviews)
Really interesting place, great price for the location too. Staff was very friendly.

Reviewed on Jan 19, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $182 total per night from Feb 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (2,552 reviews)
Did not have breakfast

Reviewed on Jan 19, 2026

Hilton 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
$106 nightly
The price is $124 total per night from Feb 9 to Feb 10
$124 total
Feb 9 - Feb 10
Total with taxes and fees
8.4/10 Very Good! (5,567 reviews)
room was emaculate and the staff were excellent as always

Reviewed on Jan 19, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,125 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 $155 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.