Oak Park Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
La Banque Hotel
Price was CA $1,383, price is now CA $889 per person
CA $889
per person
Jun 5 - Jun 10
found 5 hours ago
Roundtrip flight included
Toronto (YTO) 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
found 7 hours ago
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
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)
Rooms were modern, clean and comfortable. The staff was amazing! The concierge host, Charles, was the best. So kind, helpful, genuine and friendly.
Reviewed on Apr 27, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,812, price is now CA $1,256 per person
CA $1,256
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
We had a great time! Room was clean, spacious, and nice views! Staff was friendly and helpful. Will stay again
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 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
Fabulous food and outstanding bar and staff with a phenomenal panoramic view of the heart of Chicago. Love!!!
Reviewed on Apr 27, 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! (10,148 reviews)
Shower only had hot water about half the time, then lukewarm. This is an older hotel with very small bathroom and dated. For the price, expected better. Beds were comfortable though. Hotel does not have its own parking and the lot behind was full on Friday evening, but was able to park across the ...
Reviewed on Apr 27, 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! (2,647 reviews)
great location. clean. convenient
Reviewed on Apr 27, 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! (5,137 reviews)
Stay was lovely, small room. I booked a king room and you could tell they put two twins together to make it a king but overall, very clean & loved the shower pressure!
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
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
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.
