Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,702
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
They charge a facilities fee which is about 20 bucks a night for the amenities. I generally don't have a problem with that as it includes breakfast. BUT, I was annoyed that in the hotel gym (which isn't bad), the bikes had some problems. It's a slight nitpick, admittedly, but that's what it is. The hotel is very close to transit and the LOOP which is the main area of Chicago. Staff were amazing and helpful, the breakfast was very filling. The gym has weights that go up to 20KG, which is pretty nice and they do have those gymbro slogans on the walls which is kind of fun.
Reviewed on Aug 22, 2026
The Talbott, Autograph Collection
Downtown Chicago
CA $1,447
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
CA $1,265
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.
Reviewed on Aug 21, 2026
Ready to book your vacation to Oakbrook Terrace?
Oakbrook Terrace Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $142
CA $169 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,276 reviews)
"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests ..."
Reviewed on Aug 21, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $197
CA $234 total
Aug 23 - Aug 24
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $345
CA $405 total
Sep 11 - Sep 12
includes taxes & 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.
Stay near popular Oakbrook Terrace attractions
Drury Lane Theater
8.8/10 (93 reviews)
You can enjoy a show at Drury Lane Theater during your trip to Oakbrook Terrace. Amble around this family-friendly area's riverfront or attend a sporting event.
Loyola Medicine Oakbrook Terrace
Though Loyola Medicine Oakbrook Terrace might be what brings you to town, perhaps you'll have a chance to explore more of Oakbrook Terrace while you are here.
What to do in Oakbrook Terrace
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does an Oakbrook Terrace vacation package cost?
Offering great value package deals from CA $1,099 on Expedia, you'll be surprised at how little a vacation to Oakbrook Terrace costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oakbrook Terrace?
If you'd like to book a cheap Oakbrook Terrace vacation package, consider visiting in December, January and February. You'll generally find better rates on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Oakbrook Terrace?
The ideal length for your Oakbrook Terrace vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you time to go to all the top 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 easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Oakbrook Terrace package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Oakbrook Terrace vacation as a package?
You can enjoy significant savings on your Oakbrook Terrace retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Oakbrook Terrace?
If you're considering a spur-of-the-moment Oakbrook Terrace trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Oakbrook Terrace?
- Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Oakbrook Terrace.
- Set your budget: Factor in costs like flights, meals and transportation when calculating how much to save for your trip to Oakbrook Terrace. Then, pick a hotel that works with your budget, whether that's an economical stay or a more luxurious getaway.
- Decide how long to go for: Now that you're up to speed on Oakbrook Terrace, you can figure out the right length of your break. Put together a rough plan and allocate enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Oakbrook Terrace vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
