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.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was CA $1,551, price is now CA $1,158 per person
CA $1,158
per person
May 8 - May 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
Clean room and great staff!

Reviewed on Mar 24, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,293, price is now CA $1,451 per person
CA $1,451
per person
Jun 4 - Jun 8
found 24 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The rooftop wasn’t open, everything else was great

Reviewed on Mar 24, 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 $2,347, price is now CA $1,510 per person
CA $1,510
per person
Jun 4 - Jun 8
found 24 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Beautiful view of Lake Michigan!

Reviewed on Mar 24, 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was CA $1,970, price is now CA $1,474 per person
CA $1,474
per person
Jun 4 - Jun 8
found 24 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans! The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too! The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well! All and all it’s a wonderful place to experience!!!!🍍

Reviewed on Mar 18, 2026

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Oak Brook 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 $159 per night from Mar 25 to Mar 26
CA $159
CA $187 total
Mar 25 - Mar 26
includes taxes & fees
8/10 Very Good! (10,008 reviews)
The room is cozy and decent

Reviewed on Mar 24, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is CA $181 per night from Apr 6 to Apr 7
CA $181
CA $251 total
Apr 6 - Apr 7
includes taxes & fees
9.4/10 Exceptional! (3,619 reviews)
Breakfast was so good!! Very friendly staff !!! Clean !!

Reviewed on Mar 24, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is CA $179 per night from Apr 5 to Apr 6
CA $179
CA $210 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (5,787 reviews)
This was our first booked trip as a family of 4 and our stay was excellent. Highlight of the stay was the breakfast. We wanted to get to the pool, but it got shut down early Friday night due to an accident. Hotel is in a great spot for walking around and accessing the majority of downtown Chicago. ...

Reviewed on Mar 24, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,183 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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Discover the most popular places to visit in Oak Brook

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Chicago Skyline at North Beach

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes

What to do in Oak Brook

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $36
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Oak Brook

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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.