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 $890, price is now CA $668 per person
CA $668
per person
Sep 3 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
Hotel staff was helpful, room was comfortable & so was the bed- would stay again

Reviewed on Jun 30, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,375, price is now CA $971 per person
CA $971
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Very clean, great location. Every staff member we encountered was just terrific

Reviewed on Jun 30, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,146, price is now CA $832 per person
CA $832
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on Jul 1, 2026

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was CA $1,081, price is now CA $803 per person
CA $803
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,337 reviews)
Amazing room at a reasonable price! Great location and very friendly staff! Thank you to Jock, who made us feel welcome!

Reviewed on Jun 30, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,615, price is now CA $1,205 per person
CA $1,205
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on Jun 30, 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 $211 per night from Jul 2 to Jul 3
CA $211
CA $251 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very good! (10,183 reviews)
"The place is very old and outdated. When entering it smells wet and dust from the start. The rooms are very wet and cold inside. Highly not recommended"

Reviewed on Jul 1, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,823 reviews)
"Very clean, great location. Every staff member we encountered was just terrific"

Reviewed on Jun 30, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jul 6 to Jul 7
CA $227
CA $270 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,474 reviews)
"Friendly staff. Our room was comfortable and clean."

Reviewed on Jun 30, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,737 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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
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 $668 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.

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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.