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 $1,029, price is now CA $808 per person
CA $808
per person
Aug 28 - Aug 31
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (391 reviews)
We love Wind Creek Hotel/Casino, we have been there several times. This last time the room was clean but smelled bad.
Reviewed on May 30, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,743, price is now CA $1,186 per person
CA $1,186
per person
Aug 27 - Aug 30
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,011 reviews)
I recommend 1000/10, this hotel has everything you need and the location is everything. LOVE LOVE LOVE.
Reviewed on Jun 3, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,668, price is now CA $1,237 per person
CA $1,237
per person
Jul 9 - Jul 12
found 10 hours ago
Roundtrip flight included
Toronto (YTO) 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
Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,587, price is now CA $1,213 per person
CA $1,213
per person
Aug 7 - Aug 11
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,490 reviews)
Hotel is clean and staff is great!
Reviewed on Jun 2, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $2,023, price is now CA $1,581 per person
CA $1,581
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,370 reviews)
The hotel was very clean and a great location within Chicago close to restaurants and shopping.
Reviewed on Jun 2, 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 $194 per night from Jun 29 to Jun 30
CA $194
CA $230 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,169 reviews)
"Well located yet aged facility. Bathrooms are small and frankly nasty. It served our purpose as a base for a 3-day stay in Chicago with errands to run in the nearby area."
Reviewed on Jun 4, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $211 per night from Jun 28 to Jun 29
CA $211
CA $251 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,518 reviews)
"Clean room"
Reviewed on Jun 3, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Jun 30 to Jul 1
CA $263
CA $352 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,338 reviews)
"Great location and roof top bar!! The hotel is new and the decoration is beautiful!! Room was good and clean. The only thing I didn’t like was the bed … it was too soft. I hope they sdd boiled eggs as an option for breakfast"
Reviewed on Jun 5, 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.
