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.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,068, price is now CA $770 per person
CA $770
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (406 reviews)
I believe the staff was very attentive.
Reviewed on Jun 9, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $3,367, price is now CA $2,156 per person
CA $2,156
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (491 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
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $2,006, price is now CA $1,287 per person
CA $1,287
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
Gray stay, centrally located
Reviewed on Jun 10, 2026
Lodge Geneva National
Price was CA $2,221, price is now CA $1,517 per person
CA $1,517
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,372 reviews)
The Lodge was under construction when we stayed there so it was a little dusty - mainly outdoors.
My room was just off the lobby. The noise from the lobby overflowed to my room until they closed the fire doors. I would recommend they close them earlier ~ 9 pm.
Reviewed on Jun 8, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,868, price is now CA $2,044 per person
CA $2,044
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Unfortunately the elevators were out, at no fault of the staff. They were fantastic at trying to give the best service possible. The room was beautiful with a breathtaking view of the lake.
Reviewed on Jun 10, 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 30 to Jul 1
CA $190
CA $225 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (10,248 reviews)
"Old building that could really use a remodel. I've stayed in many hotels in the loop and somehow the sound from outside penetrated much more than most. The doormen were excellent though. They were very helpful and nice."
Reviewed on Jun 11, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $223 per night from Jul 1 to Jul 2
CA $223
CA $265 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,558 reviews)
"The hotel was clean and the rooms were decent. Did like the fact. I didn't like the fact there is no mirrors in the whole room except for the one in the bathroom. Also for the price that they charge I feel they should have had daily housekeeping but it was only offered after a 3-day stay. I asked ..."
Reviewed on Jun 11, 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 29 to Jun 30
CA $189
CA $215 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (2,647 reviews)
"The shuttle was a plus!"
Reviewed on Jun 10, 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
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
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
4.5/5(460 reviews)
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
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.
