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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,790, price is now CA $1,272 per person
CA $1,272
per person
Sep 5 - Sep 8
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Big rooms, nice lobby, and great breakfast. Good location and easy check in.
Reviewed on Jul 20, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,178, price is now CA $854 per person
CA $854
per person
Sep 5 - Sep 8
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The hotel location is excellent, the room was per expectations, and the staff were super helpful and friendly.
Reviewed on Jul 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,737, price is now CA $1,296 per person
CA $1,296
per person
Sep 5 - Sep 8
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)
The Navy Pier where this out standing property is a wonderful location in a wonderful city. The view is fantastic and the room perfect. The amenities around could not be better. Highly suggested on our side
Reviewed on Jul 20, 2026
Oak Park Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is CA $265 per night from Aug 6 to Aug 7
CA $265
CA $302 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (2,858 reviews)
"Overall, I thought the hotel was excellent, and the staff was very attentive. One thing I would have liked to see was a bar that is open all day because the hotel is close to O’Hare Airport and it’s very busy. And also host, conventions and conferences and people are always looking for an open ..."
Reviewed on Jul 20, 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 $241 per night from Aug 3 to Aug 4
CA $241
CA $286 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very good! (1,789 reviews)
"Always started the night with the bar and the staff was always very helpful. Always a great stay"
Reviewed on Jul 20, 2026
The Wade
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $416 per night from Aug 3 to Aug 4
CA $416
CA $495 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,936 reviews)
"The only thing was we asked for an extra pillow and it was never delivered."
Reviewed on Jul 19, 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.
What to do in Oak Park
Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
