Oakbrook Terrace Vacations from $173

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The Latest Oakbrook Terrace vacation packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $398, price is now $173 per person
$173
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early! There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there. This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.

Reviewed on Nov 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $599, price is now $285 per person
$285
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Rooms are lovely, bar / restaurant is top notch. Love staying at the pendry!

Reviewed on Nov 10, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $589, price is now $303 per person
$303
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special

Reviewed on Nov 11, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $442, price is now $242 per person
$242
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Clean! Staff friendly and a great location.

Reviewed on Nov 11, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,689, price is now $927 per person
$927
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Room exceptional well kept, staff extremely nice Ms Diana in the front desk and Luis in the concierge were superb

Reviewed on Nov 10, 2025

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

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
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Oakbrook Terrace

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Oakbrook Terrace

Oakbrook Terrace Hotel Deals

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
$102 nightly
The price is $119 total per night from Dec 8 to Dec 9
$119 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (5,208 reviews)
Friendly staff, well appointed room, needed more pillows and received very quickly.

Reviewed on Nov 8, 2025

Embassy Suites by Hilton Chicago Downtown River North
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
$101 nightly
The price is $119 total per night from Dec 7 to Dec 8
$119 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,271 reviews)
Very helpful staff

Reviewed on Nov 11, 2025

Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $120 total per night from Nov 13 to Nov 14
$120 total
Nov 13 - Nov 14
Total with taxes and fees
8/10 Very Good! (9,545 reviews)
It was fine in general. Location was great but view was not perfect just fine

Reviewed on Nov 9, 2025

Congress Plaza Hotel
See all 4,975 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 $173 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.

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