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.
Hilton Garden Inn Naperville/Warrenville
Price was CA $1,243, price is now CA $845 per person
CA $845
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Minor issues: The room was fairly clean. There was some dust in the bathroom, furniture and candy found on the floor under the table from the previous guests. The room was cleaned during our stay, but they did not restock our toilet paper.
Reviewed on May 5, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,609, price is now CA $1,589 per person
CA $1,589
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,408, price is now CA $948 per person
CA $948
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice.
Reviewed on May 26, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,753, price is now CA $1,209 per person
CA $1,209
per person
Aug 7 - Aug 10
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Staff was amazing and the apartment building was phenomenally clean!
Reviewed on May 28, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,616, price is now CA $1,119 per person
CA $1,119
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Love the view from the room. The room was very clean.
Reviewed on May 27, 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 $281 per night from Jun 3 to Jun 4
CA $281
CA $334 total
Jun 3 - Jun 4
includes taxes & fees
8/10 Very Good! (10,150 reviews)
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."
Reviewed on May 27, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $331 per night from Jun 16 to Jun 17
CA $331
CA $433 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,270 reviews)
"Location is perfect. And rooftop bar & view is amazing"
Reviewed on May 28, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from Jun 28 to Jun 29
CA $210
CA $250 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,484 reviews)
"I had travel delays and a situation with my husband and my luggage and they have been very nice about it . Front desk staff is very kind and professional"
Reviewed on May 27, 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.
Michigan Avenue
4.5/5(20 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
What to do in Oak Park
Skydeck - Willis Tower Admission
CA $60
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.
