Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
CA $1,192
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
A word of warning to others looking to book this hotel. My family and I booked the Old Town location for 3 nights, specifically because of plans we had in that neighborhood and its proximity to the Red/Purple lines for other plans on the far Northside and Evanston. We had opted not to rent a car because of this.
On the MORNING of check-in (as we were boarding our flight to Chicago) I got an email that they could no longer honor our reservation, and they had rebooked us at the Fulton Market location. While they offered to upgrade our suite and refund a small amt of the nightly rate to help with Uber costs, the new location was a huge inconvenience. We couldn't use the CTA as planned and ended up spending quite a bit more $ on Uber than we were compensated for. We also lost a lot of time in transit that we could have spent enjoying our limited time in the city.
While the suite and building amenities are nice, the whole situation was extremely frustrating and disappointing. We would have cancelled the reservation and booked another hotel in a more convenient location if they had given us any advance notice.
A couple of other notes of warning - there was no housekeeping for the 3 days we were there. There was also a Nespresso maker with 4 pods when we arrived, but when we asked for more the next day, they said we had to pay for them. Given how high the nightly rates are for this hotel it's surprising that no daily housekeeping nor coffee is provided.
Reviewed on Sep 16, 2026
Ready to book your vacation to Oakbrook Terrace?
Oakbrook Terrace Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $245
CA $291 total
Sep 20 - Sep 21
includes taxes & fees
8.8/10 Excellent! (5,432 reviews)
"Location is great."
Reviewed on Sep 17, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $250
CA $298 total
Oct 13 - Oct 14
includes taxes & fees
8/10 Very good! (2,249 reviews)
"The room was clean and the bed comfortable but the place is worn and needs some updates. Bedside lamp did not work on right side. Door kept sticking. Water pressure was great but the shower curtain had no magnet or suction to keep it in place. Free coffee was so so. Great location. And both Angela ..."
Reviewed on Sep 17, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $222
CA $264 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very good! (10,264 reviews)
"Clean room, funky smell tho. Super nice staff. Very helpful"
Reviewed on Sep 17, 2026
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.
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 $62
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 $946 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.
