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.
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)
The Pendry is in the heart of everything downtown. The blue line in from the airport was about a 7 minute walk from the lake stop. Rooftop bar is a nice visit as well as the lobby bar. Great staff, good vibes.
Reviewed on Jun 29, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,382, price is now CA $1,700 per person
CA $1,700
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 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)
Staff was extremely friendly and helpful! Very clean and inviting environment!
Reviewed on Jun 29, 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 1 to Jul 2
CA $211
CA $251 total
Jul 1 - Jul 2
includes taxes & fees
8/10 Very good! (10,171 reviews)
"Great place to stay in the city"
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! (1,833 reviews)
"Staff was extremely friendly and helpful! Very clean and inviting environment!"
Reviewed on Jun 29, 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! (4,483 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
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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.
