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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,268, price is now CA $823 per person
CA $823
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,509 reviews)
The room was clean, bed was good and the only "issue" was the size of the bathroom. For long stays might be something that I would not like but the stay was only 3 nights so I would say it was perfect. Gym could use some update as well, but same logic, for shorter stays the property is amazing. Great location, near everything.
Reviewed on Apr 28, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,439, price is now CA $910 per person
CA $910
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on Apr 24, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,360, price is now CA $884 per person
CA $884
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.
Reviewed on Apr 27, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,250, price is now CA $828 per person
CA $828
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,569 reviews)
The Royal Sonesta was a complete delight! They had staff available to help at all times, and they were always cheerful and friendly. I’ll definitely be back!
Reviewed on Apr 29, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
Absolutely fantastic will be back
Reviewed on Apr 27, 2026
Oak Park Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from May 25 to May 26
CA $119
CA $183 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,651 reviews)
Rooms were infrequently cleaned and we had to request soap and new towels (no we didn’t have our (no housekeeping) sign up). Other than that it was a nice stay.
Reviewed on May 1, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,140 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it
Reviewed on Apr 29, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundable
The price is CA $149 per night from May 25 to May 26
CA $149
CA $177 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,464 reviews)
Great check in and check out experience
Reviewed on Apr 29, 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
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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.
