Oak Park Vacation Packages
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Your Oak Park Vacation
With one of our vacation packages to Oak Park, you'll have endless opportunities for adventure and relaxation. There's a lot to experience, including its chic vibe and rich history. Want to explore your new surroundings? United Center, Brookfield Zoo and Portage Park are just three of the leading places to visit during your trip to Oak Park. No matter your travel plans or budget, putting together the ultimate tailored Oak Park vacation is a walk in the park with Expedia.
Top Oak Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was CA $1,258, price is now CA $947 per person
CA $947
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.4/10 Very Good! (3,926 reviews)
Overall a great stay, staff was friendly and bed was comfy.
Reviewed on Jun 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,852, price is now CA $1,331 per person
CA $1,331
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.
Reviewed on Jun 4, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,876, price is now CA $1,378 per person
CA $1,378
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on Jun 3, 2026
Pendry Chicago
Downtown Chicago
Price was CA $2,295, price is now CA $1,689 per person
CA $1,689
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,121 reviews)
I absolutely loved it! I little bit noisy but close to literally everything!
Reviewed on Jun 2, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,332, price is now CA $986 per person
CA $986
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too.
Reviewed on Jun 3, 2026
Oak Park Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Jun 29 to Jun 30
CA $202
CA $241 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,189 reviews)
"The hotel was clean for the most part. Corridors smells like soap because I truly believe the housekeeping works hard to keep them that way. Unfortunately the hotel was just old and needs much needed upgrade. The bathroom was looking noticeably old too and the water in the bath area needs to be at ..."
Reviewed on Jun 7, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $212 per night from Jun 28 to Jun 29
CA $212
CA $252 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,528 reviews)
"There isn't a coffee machine in the room one is supposed to be in the lobby but although the machines there were 4 there wasn't any tea or coffee pods."
Reviewed on Jun 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jun 29 to Jun 30
CA $218
CA $259 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,556 reviews)
"Great stay! I wasn’t sure what to expect since I didn’t know much about the hotel beforehand, but I was pleasantly surprised. The staff was friendly and welcoming, especially the team at the bar, who provided excellent service throughout our stay. The rooms were spacious and comfortable, with plenty ..."
Reviewed on Jun 7, 2026
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.
Discover the most popular places to visit in Oak Park
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oak Park
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
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.
