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 $1,439, price is now CA $990 per person
CA $990
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
The hotel was in great location downtown. The rooms and bedding was also clean and nice. We had to request a room change because the toilet and sink were not working correctly. In the new room, the bathroom sink continued to not drain. It was definitely annoying and disgusting. I probably won’t be staying here again due to the bathroom issue, but overall if that won’t bother you - it’s a good clean hotel with great staff.
Reviewed on Apr 22, 2026
The Wade
Downtown Chicago
Price was CA $2,345, price is now CA $1,421 per person
CA $1,421
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.4/10 Very Good! (1,791 reviews)
Wonderful place to stay in Chicago. Perfect location right by Navy Pier, amazing view from the window, clean rooms, comfortable beds, friendly staff, great food options.
Reviewed on Apr 23, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,961, price is now CA $1,233 per person
CA $1,233
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (449 reviews)
Everything was amazing from the staff to the amenities, the view and the cleanliness! I will definitely be booking again!
Reviewed on Apr 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,587, price is now CA $1,082 per person
CA $1,082
per person
Jul 9 - Jul 12
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
It’s a bit loud on the weekend. There is no daily housekeeping but great space and great location.
Reviewed on Apr 17, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,618, price is now CA $1,159 per person
CA $1,159
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,047 reviews)
This property is in a great location. The staff were friendly and the room was clean. The room we were in was very small and used. The building is really cool but we were super disappointed with it being under construction with no place to hang out and have a drink. We weren’t notified of the construction until right before our stay. We would have chosen somewhere else because of this.
Reviewed on Apr 21, 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 $157 per night from Apr 26 to Apr 27
CA $157
CA $185 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,124 reviews)
The room shown in the picture is not the one they put me on
Reviewed on Apr 21, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Apr 30 to May 1
CA $176
CA $207 total
Apr 30 - May 1
includes taxes & fees
8.8/10 Excellent! (5,115 reviews)
Clean room
Reviewed on Apr 23, 2026
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Apr 29 to Apr 30
CA $118
CA $180 total
Apr 29 - Apr 30
includes taxes & fees
8.2/10 Very Good! (2,629 reviews)
The hotel was in great location downtown. The rooms and bedding was also clean and nice. We had to request a room change because the toilet and sink were not working correctly. In the new room, the bathroom sink continued to not drain. It was definitely annoying and disgusting. I probably won’t be ...
Reviewed on Apr 22, 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
Skydeck - Willis Tower Admission
CA $61
per adult
96% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
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.
