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 $991, price is now CA $699 per person
CA $699
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,500 reviews)
Great customer service. Staff was very friendly.
Reviewed on Apr 20, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,293, price is now CA $1,570 per person
CA $1,570
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
The Langham is simply unparalleled! The staff, the amenities, the location, food and level of service are at such a high level, I find it unmatched anywhere else. Simply cannot wait to come back
I actually came to Chicago to see a concert, I had bought the tickets and the air travel and knew I was going to stay at the Langham but FORGOT to reserve the room! The staff worked with me for 1/2 an hour to shoehorn me into the almost capacity hotel for 2 nights! Amazong
Reviewed on Apr 18, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,342, price is now CA $921 per person
CA $921
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,409 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
Swissotel - Chicago
Downtown Chicago
Price was CA $2,502, price is now CA $1,797 per person
CA $1,797
per person
Jun 24 - Jun 27
found 24 hours ago
Roundtrip flight included
Winnipeg (YWG) to Chicago (ORD)
9/10 Wonderful! (3,266 reviews)
Great location, service wasn’t the greatest, fees are high, crib was outdated.
Reviewed on Apr 13, 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! (10,155 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 $119 per night from Apr 26 to Apr 27
CA $119
CA $181 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (2,632 reviews)
Very nice location with lots of things in walkable distance. The only negative was the small room size. There wasn't a closet but the room was functional. It also had a small refrigerator and microwave. I would stay here again.
Reviewed on Apr 20, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundable
The price is CA $147 per night from Apr 30 to May 1
CA $147
CA $173 total
Apr 30 - May 1
includes taxes & fees
8.8/10 Excellent! (3,440 reviews)
Great stay
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
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
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.
