Oakbrook Terrace Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Oakbrook Terrace Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Price was CA $1,073, price is now CA $732 per person
CA $732
per person
Aug 21 - Aug 23
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Great stay perfect location

Reviewed on Jul 12, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,662, price is now CA $1,086 per person
CA $1,086
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!

Reviewed on Jul 13, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,822, price is now CA $1,244 per person
CA $1,244
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Main area was nice. Hotel room was outdated

Reviewed on Jul 13, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $2,007, price is now CA $1,425 per person
CA $1,425
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
Probably the best hotel I ever stayed at next time. Make sure I get a room with a view of the lake for five stars.

Reviewed on Jul 12, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,251, price is now CA $909 per person
CA $909
per person
Oct 1 - Oct 4
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
Would stay here again! Great hotel

Reviewed on Jul 13, 2026

Ready to book your vacation to Oakbrook Terrace?

 

Choose your dates

Oakbrook Terrace Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 3 to Aug 4
CA $239
CA $273 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (2,830 reviews)
"Nice ,clean ,staff was friendly"

Reviewed on Jul 12, 2026

Hyatt Regency O'Hare Chicago
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 $218 per night from Jul 27 to Jul 28
CA $218
CA $259 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,740 reviews)
"This place will charge you a resort fee that doubles the cost of your stay. They also won’t communicate that to you or give you any receipts. Don’t stay here."

Reviewed on Jul 12, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 $310 per night from Aug 10 to Aug 11
CA $310
CA $416 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,914 reviews)
"Main area was nice. Hotel room was outdated"

Reviewed on Jul 13, 2026

Omni Chicago Hotel
See all 4,743 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $31
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 $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and 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 $732 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.