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.
La Banque Hotel
Price was CA $1,056, price is now CA $718 per person
CA $718
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,955, price is now CA $1,149 per person
CA $1,149
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,179, price is now CA $763 per person
CA $763
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Loved the hotel and ambiance. My stay was truly amazing. I just wish they would’ve had an ice machine and microwaves inside the hotel . It would’ve been 5 stars if they had microwaves and ice. Also the receptionist attitude wasn’t the best. I didn’t feel very welcomed and seemed like she was just trying to rush me away.
Reviewed on Feb 26, 2026
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,317, price is now CA $951 per person
CA $951
per person
May 5 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.
Reviewed on Feb 26, 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 $122 per night from Feb 27 to Feb 28
CA $122
CA $144 total
Feb 27 - Feb 28
includes taxes & fees
8/10 Very Good! (9,937 reviews)
Shortly after our check in when noticed our room did not have heat called the operator only to be told the hotels boiler was out, had to call a 2nd time because the toilet wouldn't flush finally when the maintenance guy came to fix the toilet he said he could get us a space heater we was so excited ...
Reviewed on Feb 26, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Mar 4 to Mar 5
CA $175
CA $244 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,416 reviews)
Loved the hotel and ambiance. My stay was truly amazing. I just wish they would’ve had an ice machine and microwaves inside the hotel . It would’ve been 5 stars if they had microwaves and ice. Also the receptionist attitude wasn’t the best. I didn’t feel very welcomed and seemed like she was just ...
Reviewed on Feb 26, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Mar 4 to Mar 5
CA $140
CA $165 total
Mar 4 - Mar 5
includes taxes & fees
8.6/10 Excellent! (5,685 reviews)
Service was great, and the staff was very kind.
Reviewed on Feb 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.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
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 90-min Chicago River Architecture Tour
CA $55
per adult
94% 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.
