Oakbrook Terrace Vacation Packages

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Top Oakbrook Terrace Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,195, price is now CA $942 per person
CA $942
per person
Jan 21 - Jan 24
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,321, price is now CA $978 per person
CA $978
per person
Jan 21 - Jan 24
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,324, price is now CA $1,004 per person
CA $1,004
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Very walkable to Michigan Avenue with chic modern designs in a vintage building. Friendly staff. Stayed for one night, very comfortable and clean room.

Reviewed on Nov 6, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,731, price is now CA $1,315 per person
CA $1,315
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
Beautiful rooms and service.

Reviewed on Nov 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,457, price is now CA $1,902 per person
CA $1,902
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint

Reviewed on Nov 6, 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 $162 per night from Nov 24 to Nov 25
CA $162
CA $193 total
Nov 24 - Nov 25
includes taxes & fees
8/10 Very good! (10,108 reviews)
"Beautiful hotel. Asked for adjoining rooms and was accommodated. Comfortable beds and pillows. Would stay again."

Reviewed on Nov 6, 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 $162 per night from Nov 11 to Nov 12
CA $162
CA $193 total
Nov 11 - Nov 12
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 refundable
The price is CA $154 per night from Nov 15 to Nov 16
CA $154
CA $183 total
Nov 15 - Nov 16
includes taxes & fees
8.8/10 Excellent! (5,585 reviews)
"Excellent location for a very convenient price and located in a historical, beautiful building! Rooms are small but comfortable."

Reviewed on Nov 6, 2026

River Hotel
See all 4,769 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 $942 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.