Oak Brook Vacation Packages

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Your Oak Brook Vacation

Come and discover this fascinating city for yourself with a Oak Brook vacation package. Consider spending some time in the neighborhood of North Lawndale, which is great for golfing and walking, and your time here is bound to be unforgettable. Brookfield Zoo, Morton Arboretum and Oakbrook Center Mall are just some of the many attractions worth exploring during your trip to Oak Brook. Expedia will help you escape your routine. Tailor your vacation to Oak Brook to match your travel style, whatever that may look like.

Top Oak Brook Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,523, price is now CA $1,051 per person
CA $1,051
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Mediocre all around and for the price point not worth it. Great location. But nothing else compelling. Food was only ok. Service was only ok. Nothing memorable. Will seek somewhere else next time.

Reviewed on Jul 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $7,380, price is now CA $4,994 per person
CA $4,994
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on Jul 8, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,290, price is now CA $1,614 per person
CA $1,614
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 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 $3,176, price is now CA $2,335 per person
CA $2,335
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
View was beautiful, accommodations were excellent.

Reviewed on Jul 8, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $2,776, price is now CA $2,140 per person
CA $2,140
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
This hotel was located perfectly to see downtown Chicago. The rooms were beautiful and the staff was wonderful. We had booked some mobility scooters to get around downtown. We had no issues getting them up to our rooms.

Reviewed on Jul 9, 2026

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Oak Brook Hotel Deals

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! (1,721 reviews)
"Great location Lovely 🍸"

Reviewed on Jul 9, 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 $294 per night from Aug 9 to Aug 10
CA $294
CA $396 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (1,886 reviews)
"The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances."

Reviewed on Jul 8, 2026

Omni Chicago Hotel
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 $263 per night from Aug 6 to Aug 7
CA $263
CA $312 total
Aug 6 - Aug 7
includes taxes & fees
8/10 Very good! (10,212 reviews)
"Perfect location right across the park for a phenomenal price. Room was a little warm but the fan could keep the temp down thankfully."

Reviewed on Jul 9, 2026

Congress Plaza Hotel
See all 4,973 properties in Oak Brook
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 Oak Brook attractions

A golf course with a large tree in the foreground, a pond, and a clear sky.

Oak Brook Golf Course

8.2/10 (147 reviews)
Enjoy a round of golf in Oak Brook at Oak Brook Golf Course. Stroll along the riverfront or attend a sporting event in this family-friendly area.
See properties

What to do in Oak Brook

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 Oak Brook

Frequently asked questions

How much does an Oak Brook vacation package cost?
You'll find cheap prices from CA $1,051 on Expedia for your Oak Brook break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Oak Brook costs.
What are the cheapest months to go to Oak Brook?
January, February and April are great times to search for cheap Oak Brook vacation packages. Opting to travel in quieter months means you can typically find lower prices on hotels and flights.
How many days is enough for Oak Brook?
Dedicate around 2 days for your Oak Brook vacation to take in everything that makes this place unique. Explore key neighbourhoods, including Yorkfield and York Centre. Then check out top attractions like Yorktown Shopping Centre and Galloping Ghost. With a well-organized itinerary, you'll be kept busy with room for some relaxation too. Want to venture outside of Oak Brook? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Oak Brook?
Boasting a host of highlights starting with its top-notch golfing, Oak Brook is a good vacation destination. Whether you'd like to check out attractions like Mayslake Peabody Mansion and Lizzadro Museum of Lapidary Art or take the road less travelled, you'll find plenty to keep you busy during your Oak Brook vacation.
How to find the best Oak Brook package deals?
Use Expedia's filter tool to find some tempting Oak Brook package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Oak Brook package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Oak Brook vacation as a package?
You can enjoy significant savings on your next Oak Brook getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Oak Brook?
If you're planning a spontaneous Oak Brook getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Oak Brook?

  1. Pick your travel dates: The things you'd like to do in Oak Brook and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to Oak Brook. Then, choose a property that fits your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Oak Brook. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick an Oak Brook vacation package that brings all your bookings together.

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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.