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.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,526, price is now CA $1,069 per person
CA $1,069
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Hamilton (YHM) 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,916, price is now CA $1,246 per person
CA $1,246
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Hard to find the parking . Everything at navy pier closes at 8pm . Staff offered no extras even though it says we are vip Expedia and hiltons honors .
Reviewed on Apr 17, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $2,226, price is now CA $1,481 per person
CA $1,481
per person
May 26 - May 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (2,120 reviews)
The stay was pleasant.
Reviewed on Apr 19, 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
Oak Park Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Apr 26 to Apr 27
CA $158
CA $185 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,150 reviews)
Great stay
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! (2,628 reviews)
If you have a car be prepared to pay 50/night for parking which is pretty common for all downtown properties. This property is affordable so it does offset the cost.fpr parking. Smaller rooms are perfect for solo traveler or a very close couple lookingfor an intimate space. The only other thing is ...
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 29 to Apr 30
CA $147
CA $173 total
Apr 29 - Apr 30
includes taxes & fees
8.8/10 Excellent! (3,435 reviews)
You get what you pay for. Roaches in the stairway and a serve yourself amenity closet. Good location.
Reviewed on Apr 19, 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.
