Oak Park Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 13 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 $1,417, price is now CA $1,029 per person
CA $1,029
per person
Aug 13 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,316, price is now CA $1,001 per person
CA $1,001
per person
Aug 30 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,735 reviews)
Fantastic location and rooftop view! Very clean and professional staff!
Reviewed on Jun 12, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,286, price is now CA $980 per person
CA $980
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,966 reviews)
The staff was able to help us get a room earlier than the check-in time.
Reviewed on Jun 9, 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 $225 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,251 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 $201 per night from Jun 14 to Jun 15
CA $201
CA $239 total
Jun 14 - Jun 15
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
