
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 $720, price is now CA $555 per person
CA $555
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026


Level Chicago – Old Town
Downtown Chicago
Price was CA $3,614, price is now CA $2,421 per person
CA $2,421
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026

The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,313, price is now CA $936 per person
CA $936
per person
Aug 30 - Sep 3
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
Always a pleasure and a great location
Reviewed on Jun 24, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $2,819, price is now CA $2,098 per person
CA $2,098
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 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 $231 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (10,125 reviews)
"Parking was difficult, trying to trek luggage around and find parking was terrible, but the staff was helpful. You can pull in front of the hotel and unload and they will hold your luggage. There is a parking lot behind the hotel, spaces were very tight and prices were about $45 a night. Hotel was ..."
Reviewed on Jun 25, 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Jul 6 to Jul 7
CA $228
CA $271 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,458 reviews)
"Room was large but the hotel is very dated. It was clean, which is the most important factor and it was also in a convenient location."
Reviewed on Jun 25, 2026

Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Jul 5 to Jul 6
CA $255
CA $344 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (4,534 reviews)
"First time in Chicago and we picked the perfect hotel to stay! Great location, very nice, clean hotel, helpful staff… would stay here again if we come back!"
Reviewed on Jun 25, 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.
What to do in Oak Park

Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% 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.













