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.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,080, price is now CA $782 per person
CA $782
per person
Sep 4 - Sep 7
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (406 reviews)
Overall, this hotel is very nice! The bed was comfortable with clean sheets. The shower was amazing, they have Starbucks downstairs and a steakhouse on the 17th floor! The only downside was the pool seemed very foggy and the hot tub was NOT clean! There was some buildup of dirt in the hot tub. Also, the lights in our room were acting weird at some points which was kind of spooky.
Reviewed on Jun 7, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,418, price is now CA $1,704 per person
CA $1,704
per person
Sep 1 - Sep 6
just found
Roundtrip non-stop flight included
Vancouver (YVR) 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,855, price is now CA $1,370 per person
CA $1,370
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)
This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually.
Reviewed on Jun 8, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,815, price is now CA $1,368 per person
CA $1,368
per person
Jul 16 - Jul 19
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times.
The hotel offered only coffee/tea and fresh fruit until 9am.
The staff made our stay more enjoyable.
Reviewed on Jun 8, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,351, price is now CA $1,021 per person
CA $1,021
per person
Jul 17 - Jul 20
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.4/10 Very Good! (1,954 reviews)
Very comfortable bed, spacious room, and great location!
Reviewed on Jun 8, 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 $189 per night from Jun 29 to Jun 30
CA $189
CA $225 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,221 reviews)
"Fantastic room and location."
Reviewed on Jun 9, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
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! (1,545 reviews)
"Our room was spacious and very clean"
Reviewed on Jun 8, 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 $230 per night from Jun 29 to Jun 30
CA $230
CA $273 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,569 reviews)
"Honestly during my trip I stayed at 6 Chicago hotels and this one was my favorite along with the Midlan hotel. Both exquisite, don’t forget to check out the roof top! I almost left without seeing the view it gorgeous!"
Reviewed on Jun 8, 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 $56
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.
