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.
Level Chicago - River North
Downtown Chicago
Price was CA $1,578, price is now CA $1,025 per person
CA $1,025
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
The place was spacious and well decorated. Location was great and staff was friendly. We did not use the amenities but the 6th floor was amazing! The two things that could be a lot better: shower pressure and blackout curtains. I am a very light sleeper and the room was filled with daylight as early as 4:45am in June. Shower had no pressure and very little water. Overall was a great stay!
Reviewed on Jun 15, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,631, price is now CA $1,896 per person
CA $1,896
per person
Aug 24 - Aug 28
found 24 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.
Reviewed on Jun 14, 2026
The Emily Hotel
Downtown Chicago
Price was CA $2,406, price is now CA $1,755 per person
CA $1,755
per person
Aug 1 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.
Reviewed on Jun 15, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,401, price is now CA $1,787 per person
CA $1,787
per person
Aug 1 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
The hotel was wonderful. Everything was extremely clean, the entire staff was very friendly, and the service was exceptional. We had the best experience
Reviewed on Jun 14, 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 $191 per night from Jun 29 to Jun 30
CA $191
CA $227 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,286 reviews)
"This is the second time I’ve stayed at this property. It is conveniently located and the rooms facing the lake have a gorgeous view (request lake view). The room lighting was poor, and I missed having a table on each side of the bed."
Reviewed on Jun 16, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Jun 30 to Jul 1
CA $191
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,592 reviews)
"Clean room staff nice"
Reviewed on Jun 15, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Jun 29 to Jun 30
CA $189
CA $216 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (2,676 reviews)
"Aside from the liberal marketing and CNN programming everywhere, it was a nice experience."
Reviewed on Jun 15, 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.
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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.
