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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,941, price is now CA $1,396 per person
CA $1,396
per person
Sep 4 - Sep 7
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.
Reviewed on Jun 12, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,519, price is now CA $1,105 per person
CA $1,105
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Oak Park Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jun 29 to Jun 30
CA $190
CA $226 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,252 reviews)
"The only negative I had with the hotel was that their food choices were limited, and there were not a lot of healthy options. I would have really appreciated more veg choices with the meals, and more salad options."
Reviewed on Jun 12, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $202 per night from Jun 30 to Jul 1
CA $202
CA $240 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,568 reviews)
"I"
Reviewed on Jun 12, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Jun 28 to Jun 29
CA $222
CA $253 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,656 reviews)
"I really liked it and recommend it."
Reviewed on Jun 12, 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.
