Oakbrook Terrace Vacations from $363
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The Latest Oakbrook Terrace vacation packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
$460
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Everyone was so nice and accommodating. The location is great. We had a great view of the river.
Reviewed on Oct 15, 2026
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See all available trips from Columbus to Oakbrook Terrace
View all tripsStay near popular Oakbrook Terrace attractions
Drury Lane Theater
8.8/10 (93 reviews)
This historic theater 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.
What to do in Oakbrook Terrace
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
Oakbrook Terrace Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
$126 total
Nov 11 - Nov 12
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
$181 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (5,524 reviews)
"We got both an unexpected upgrade & early check in when we arrived! Not only is it in an ideal location, but there are perks like a water bottle filling station on each floor & a free espresso/coffee bar station on 2nd floor. Hotel staff was always responsive to our questions at the desk during our ..."
Reviewed on Oct 15, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$142 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
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 $363 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.