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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,495, price is now CA $1,045 per person
CA $1,045
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
The staff was fantastic. Our plane arrived late, we were starving, didn’t know where to go or even have a plan, and the staff jumped right in and directed us to the perfect place: Portillo’s. They came up with lots of great suggestions that fit exactly what we wanted to do and where to eat. The rates were very reasonable, it’s situated in the middle of downtown, lots of restaurants on the same block, and plenty of Chicago nightlife. I would definitely stay there again.
Reviewed on Jun 7, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,026, price is now CA $1,419 per person
CA $1,419
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,852, price is now CA $1,331 per person
CA $1,331
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.
Reviewed on Jun 4, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,876, price is now CA $1,378 per person
CA $1,378
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on Jun 3, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $2,142, price is now CA $1,575 per person
CA $1,575
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too.
Reviewed on Jun 3, 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 $189 per night from Jun 29 to Jun 30
CA $189
CA $225 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,195 reviews)
"Convenient to many interesting and beautiful places in Chicago. The hotel was well maintained and the staff was attentive and efficient."
Reviewed on Jun 7, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $212 per night from Jun 28 to Jun 29
CA $212
CA $252 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,533 reviews)
"I had read the evaluations after I booked the hotel and was quite anxious. It turned out that everything was fine. There were no additional charges except for the incidental charge. Service and staff were excellent. I really recommend this hotel especially if you want to stay in a central ..."
Reviewed on Jun 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Jun 29 to Jun 30
CA $230
CA $273 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,564 reviews)
"No water sold in the hotel. Instead they tried to upsell me in a package that I didn’t need. Think you need to change that policy. Our entire group of 4 rooms were disappointed."
Reviewed on Jun 7, 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
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
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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.
