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.
Chicago Athletic Association, a Hyatt Hotel
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 20 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
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
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
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
ENVITAE Hotel 4 Bedroom Luxury Apartments
Near North Side
Price was CA $3,341, price is now CA $2,376 per person
CA $2,376
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (16 reviews)
⭐⭐⭐⭐⭐
We had a fantastic stay in this 4-bedroom apartment hotel. Looks exactly like the pictures. The unit was spotlessly clean and perfectly appointed — it truly felt like a home away from home. The kitchen had every amenity you could possibly need, which made cooking and relaxing with family incredibly easy.
The bedding was beautiful and very comfortable, and having a washer and dryer in the unit was a huge bonus, especially for a longer stay.
The building itself felt very secure, including the parking area, which gave us great peace of mind. We also loved the amenities — the gym and lounge area were excellent and well maintained.
Overall, this was one of the best apartment-style stays we’ve had. Comfortable, convenient, and thoughtfully set up. We would absolutely stay here again.
Reviewed on Mar 5, 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 $185 per night from May 27 to May 28
CA $185
CA $219 total
May 27 - May 28
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
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
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! (4,243 reviews)
"Great staff with a clean room."
Reviewed on May 25, 2026
The Chicago Hotel Collection - Magnificent Mile
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
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
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
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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.
