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 Wade
Downtown Chicago
Price was CA $2,345, price is now CA $1,344 per person
CA $1,344
per person
Jun 3 - Jun 8
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.4/10 Very Good! (1,791 reviews)
I had a short stay, but it was truly a great experience. I only stayed for one night, and from the moment I arrived, the service was friendly and efficient. The room was clean, comfortable, and well-maintained—perfect for getting a good night’s rest.
The next morning, the breakfast was definitely the highlight of my stay. Everything was fresh, delicious, and well-prepared. It was the perfect way to end my visit on a high note.
I would definitely come back and highly recommend this hotel.
Reviewed on Apr 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,116, price is now CA $1,894 per person
CA $1,894
per person
Jun 3 - Jun 8
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,463 reviews)
No restaurant or available food after 10pm.
Reviewed on Apr 21, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $2,699, price is now CA $1,752 per person
CA $1,752
per person
Jun 3 - Jun 8
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,417 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Price was CA $2,138, price is now CA $1,466 per person
CA $1,466
per person
Jun 3 - Jun 8
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
Clean rooms. Close to public transportation. Safe area.
Reviewed on Apr 18, 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 $159 per night from Apr 26 to Apr 27
CA $159
CA $187 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,160 reviews)
Hotel has the markings of being grand, but needs a renovation in a lot of areas. The biggest issue we had is that the a/c is not adjustable in each room and the building was very warm on the 75 degree day in April. We called the front desk and they did bring us a fan that helped some and we realized ...
Reviewed on Apr 20, 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 27 to Apr 28
CA $118
CA $181 total
Apr 27 - Apr 28
includes taxes & fees
8.2/10 Very Good! (2,635 reviews)
The room was actually pretty good and pretty good size for two people and a queen bed I really loved it and I would go back again.
Reviewed on Apr 21, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Apr 28 to Apr 29
CA $173
CA $203 total
Apr 28 - Apr 29
includes taxes & fees
8.8/10 Excellent! (3,445 reviews)
Breakfast was not included but there is a restaurant colliding (Elephant and Castle). The West Adam’s Club Quarters is an old and outdated property but room was ok, cleaned daily and the staff super friendly. Location was unique, it is near a lot of opportunities to see points of interest in this ...
Reviewed on Apr 20, 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
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.
