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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,536, price is now CA $1,094 per person
CA $1,094
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
I feel very glad my husband and I chose Felix Hotel for our stay in Chicago during early June. The location was great for our purposes, there were plenty of food options near by and the complementary fruit and coffee/tea in the morning was very helpful to get our day started. We felt specially welcomed by Crystal at the front desk. Her friendly personality will be forever remembered as one of the highlights of a wonderful trip.
Reviewed on Jun 18, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 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 - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Great Wolf Lodge Illinois
Price was CA $2,088, price is now CA $1,422 per person
CA $1,422
per person
Aug 2 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
First time staying at a Great Wolf Lodge. Was a wonderful time. Onsite food selection was great and easy to order ahead of time if wanted. Waterpark was as expected. Many other activities available to keep the kids entertained was a nice touch. Arcade is expensive and having to pay to park were my only disappointments. Otherwise highly recommend!
Reviewed on Jun 18, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,839, price is now CA $1,302 per person
CA $1,302
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)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!
Reviewed on Jun 18, 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 $193 per night from Jun 29 to Jun 30
CA $193
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"The facilities are very old, and there is a musty smell in the room."
Reviewed on Jun 18, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $193 per night from Jul 1 to Jul 2
CA $193
CA $230 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,595 reviews)
"seems like we are visiting every other month to meet up with friends. We have already recommended this hotel many times and will definitely be staying again."
Reviewed on Jun 19, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jul 3 to Jul 4
CA $203
CA $231 total
Jul 3 - Jul 4
includes taxes & fees
8.8/10 Excellent! (2,671 reviews)
"Great staff and amenities"
Reviewed on Jun 19, 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.
Discover the most popular places to visit in Oak Park
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oak Park
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $69
per adult
94% of travellers recommend
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.
