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 Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,444, price is now CA $1,056 per person
CA $1,056
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,655 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on May 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,155, price is now CA $1,480 per person
CA $1,480
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,548, price is now CA $1,099 per person
CA $1,099
per person
Jul 9 - Jul 12
found 1 day 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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $183 per night from May 26 to May 27
CA $183
CA $217 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,218 reviews)
Great location for a good price. Staff was helpful and the place was nice. It’s a little older building and shows a bit of wear here and there but not a bad spot at all. Overall worth the price!e
Reviewed on May 12, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from May 25 to May 26
CA $204
CA $281 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,119 reviews)
El desayuno estuvo bien
Reviewed on May 12, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from May 25 to May 26
CA $204
CA $243 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,299 reviews)
Very friendly and professional staff on all levels. Location in Chicago is second to none. The food in the restaurant was delicious. But it's obvious structure-wise that Hilton has cut corners with cheap room furniture, bathroom had loose and rusted shower head and handle etc. Lamps looked like garage ...
Reviewed on May 12, 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 $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.
