Oak Brook 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

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.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,769, price is now CA $1,257 per person
CA $1,257
per person
Aug 10 - Aug 15
found 19 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Great place to stay and excellent breakfast choices

Reviewed on May 14, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,271, price is now CA $1,438 per person
CA $1,438
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 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 $3,275, price is now CA $2,074 per person
CA $2,074
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Walls are paper thin. We literally heard snoring all night from the room next to us. Also, the smell of cigarette smoke kept coming into our room. Rooms were nice and clean. The view was 🔥.

Reviewed on May 23, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $2,988, price is now CA $1,971 per person
CA $1,971
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Super location, good crowd of staff and fellow travellers. Smells great!

Reviewed on May 24, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was CA $4,234, price is now CA $3,009 per person
CA $3,009
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,361 reviews)
Excellent hotel and close to restaurants and shopping. Very clean.

Reviewed on May 24, 2026

Ready to book your vacation to Oak Brook?

 

Choose your dates

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 $185 per night from May 26 to May 27
CA $185
CA $219 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,140 reviews)
"tiniest room i’ve ever stayed in and shower leaked all over the floor and"

Reviewed on May 25, 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 $330 per night from Jun 16 to Jun 17
CA $330
CA $432 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,242 reviews)
"Beautiful!"

Reviewed on May 25, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from May 27 to May 28
CA $210
CA $250 total
May 27 - May 28
includes taxes & fees
7.8/10 Good! (1,468 reviews)
"The rooftop bar was amazing? The location was great! The room was old and musty smelling. The carpet was wet and the floors felt uneven. The beds were comfortable! There weren’t enough elevators to support the volume of guests. The valet parking was very expensive compared to other hotels. The DJ ..."

Reviewed on May 25, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 5,239 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Oak Brook

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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
Navy Pier

Navy Pier

4.5/5(460 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Oak Brook

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Oak Brook

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.