
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 $1,256, price is now CA $866 per person
CA $866
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
Room clean, staff amazing. Old, tired property.
Reviewed on Jun 30, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,665, price is now CA $1,162 per person
CA $1,162
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Muriel at the front desk made our 54th
Anniversary memorable as she upgraded our room to a suite and sent a bottle of Prosecco and box of chocolates to our room plus a voucher for oysters at the restaurant. Kudos to her for being so kind and thoughtful. Thank you so much!!
Reviewed on Jun 30, 2026

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,403, price is now CA $1,007 per person
CA $1,007
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good.
Reviewed on Jun 30, 2026


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,770, price is now CA $1,290 per person
CA $1,290
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great location on the Navy Pier. Easy to walk places or even catch a water taxi. Room had an amazing view and was very clean. The staff were all nice and helpful. Restaurants and coffee shop on site.
Reviewed on Jun 30, 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 $211 per night from Jul 2 to Jul 3
CA $211
CA $251 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very good! (10,174 reviews)
"Very poor check-in experience. Initially couldn’t find the reservation, told me no rooms available, then only a smoking room, then a colleague stepped in and sorted the situation. Poor attitude and borderline rude which isn’t lovely after a long journey! Room was very poor. Noisy old aircon unit ..."
Reviewed on Jun 30, 2026

Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,821 reviews)
"Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good."
Reviewed on Jun 30, 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jul 6 to Jul 7
CA $227
CA $270 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,484 reviews)
"I booked three rooms at this hotel for a speacial occasion trip to celebrate a graduation. At check in I asked if one of the rooms could possibly have some kind of view of the city. I was quickly told it was not possible as the hotel was sold out. I was very sorry that out of the 100's of rooms in ..."
Reviewed on Jun 30, 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 Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Frequently asked questions
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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.













