
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)
I loved how simple and easy it was to access everything.
Reviewed on Jun 16, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,838, price is now CA $1,230 per person
CA $1,230
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Beautiful hotel. Very clean which is very important to me. Couldn’t have asked for a more perfect location. Food and drink prices at the restaurant/bar were high. Other than that, would highly recommend.
Reviewed on Jun 16, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,961, price is now CA $1,396 per person
CA $1,396
per person
Sep 2 - Sep 6
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (484 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

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 1 day 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 24 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
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 30 to Jul 1
CA $191
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (10,292 reviews)
"I understand that this is a historic property built in 1893 and it definitely has that charm, but the upkeep and amenities were surprisingly lacking. My curtains didn't close in my room, the paint in stairwells was peeling off the walls and the shower head and shower curtain hooks were cheap plastic. ..."
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 $223 per night from Jul 1 to Jul 2
CA $223
CA $266 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,595 reviews)
"Amazing food, and drinks on the rooftop with an amazing view"
Reviewed on Jun 16, 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 28 to Jun 29
CA $189
CA $216 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,679 reviews)
"I"
Reviewed on Jun 16, 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.












