Oakbrook Terrace Vacation Packages

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Top Oakbrook Terrace Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,117, price is now CA $818 per person
CA $818
per person
Dec 20 - Dec 23
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.

Reviewed on Nov 13, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,281, price is now CA $1,610 per person
CA $1,610
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,217, price is now CA $919 per person
CA $919
per person
Jan 24 - Jan 26
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $1,145, price is now CA $928 per person
CA $928
per person
Jan 24 - Jan 26
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (953 reviews)
The wellness center was my favorite!

Reviewed on Nov 8, 2026

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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
The price is CA $165 per night from Nov 24 to Nov 25
CA $165
CA $197 total
Nov 24 - Nov 25
includes taxes & fees
8/10 Very good! (10,071 reviews)
"Congress Plaza Hotel was an ideal hotel for its location to many Chicago sites. It is in walking distance to Soldier's Field which allowed us to get to the football game without dealing with traffic issues. Parking was easy to access and the lot was conveniently located behind the hotel."

Reviewed on Nov 13, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Nov 15 to Nov 16
CA $165
CA $196 total
Nov 15 - Nov 16
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Dec 10 to Dec 11
CA $151
CA $180 total
Dec 10 - Dec 11
includes taxes & fees
River Hotel
See all 4,781 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.
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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.
See properties

What to do in Oakbrook Terrace

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Oakbrook Terrace

Frequently asked questions

How much does an Oakbrook Terrace vacation package cost?
Offering great value package deals from CA $818 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.