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 Marriott Suites Deerfield
Price was CA $745, price is now CA $514 per person
CA $514
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
I booked this property after a day at O'Hare airport and multiple flight cancellations. I was greeted and checked in efficiently, had a drink and dinner and retired to a very comfortable and clean room. Breakfast the next day consusted of an excellent omelet. Overall a very comfortable and well appointed hotel. Thank you!
Reviewed on Mar 16, 2026
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,024, price is now CA $694 per person
CA $694
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (336 reviews)
If you extend your stay you have to go down to the front desk in the morning to sign a new form and, depending on what time it is, they may not be capable of renewing your keys at that time which means you have to return again later in the day. When they asked if I wanted housekeeping I said yes and, even though I was gone from my room for 12 hours I didn't get it. Then there was a knock on my door at 10 pm when I was falling asleep and I found towels outside the door the next morning. That's not what I call housekeeping.
Reviewed on May 1, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,704, price is now CA $1,161 per person
CA $1,161
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (946 reviews)
Rooms were cleaned I liked how secure the hotel was.
Reviewed on Apr 29, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,962, price is now CA $1,345 per person
CA $1,345
per person
Jun 25 - Jun 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Oak Park Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 25 to May 26
CA $118
CA $182 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,665 reviews)
Basic but clean hotel with a good location, you’re clearly paying for the spot. However, the bathroom design is a major downside. It’s too minimalist and impractical; the shower is cramped for tall guests and water leaks everywhere.
Reviewed on May 3, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from May 25 to May 26
CA $172
CA $205 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,156 reviews)
Staff was very friendly!
Reviewed on May 3, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from May 10 to May 11
CA $188
CA $224 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (4,247 reviews)
I don’t understand the excellent reviews at this hotel. The hotel was in a great location. However the room was very dated and smelled of mildew and mold. Shower was filthy. Furniture was falling apart. Would not stay here again.
Reviewed on May 2, 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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
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
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 $61
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.
