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 $1,524, price is now CA $1,030 per person
CA $1,030
per person
Jun 11 - Jun 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (327 reviews)
The staff provided Excellent customer service!!
Reviewed on Apr 25, 2026
La Banque Hotel
Price was CA $1,779, price is now CA $1,190 per person
CA $1,190
per person
Jun 11 - Jun 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (480 reviews)
The staff was friendly and the bed was very comfortable! Easy to find parking, many food options within walking distance.
Reviewed on Apr 21, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,873, price is now CA $1,261 per person
CA $1,261
per person
Jun 19 - Jun 22
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
I was blown away by our room. So big, clean. Also the 8th floor amenities were amazing! Will definitely be back! Everything about this place was incredible and so clean!
Reviewed on Apr 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,254, price is now CA $1,578 per person
CA $1,578
per person
Jun 4 - Jun 7
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
The Trump Hotel was located in the best center place possible in the heart of Downtown Chicago, walkable distance to literally everything, bars, restaurants, tourist attractions, walk by the river and boat tours, magnificent mile, millennium park and the bean, the willis skydeck... it's also Super clean! Fresh nice smell in the hallways and the rooms. Lake view room had the entire Downtown and the lake view covered. Super amazing!!!! Amenities top notch. Very polite and friendly staff. Terrace 16 was a little slow but amazing food and ambiance. Highly recommended!
Reviewed on Apr 24, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,813, price is now CA $1,276 per person
CA $1,276
per person
Jun 10 - Jun 14
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Room was cozy, clean, comfortable! Staff very friendly and in great location
Reviewed on Apr 25, 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 $182 per night from May 8 to May 9
CA $182
CA $217 total
May 8 - May 9
includes taxes & fees
8/10 Very Good! (10,145 reviews)
A family emergency came up that shortly after booking prevented me from being able to attend at all. Expedia approved for a full refund and needing the hotel's acceptance reached out in multiple ways including an email requesting acceptance of such but we have not heard back and it is now the next ...
Reviewed on Apr 26, 2026
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 Apr 28 to Apr 29
CA $119
CA $181 total
Apr 28 - Apr 29
includes taxes & fees
8.2/10 Very Good! (2,643 reviews)
Staff was so kind and great!
Reviewed on Apr 26, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from May 25 to May 26
CA $161
CA $192 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,133 reviews)
Wish they had a mini fridge
Reviewed on Apr 26, 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
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.
