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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,809, price is now CA $1,248 per person
CA $1,248
per person
Aug 26 - Aug 29
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,849, price is now CA $1,308 per person
CA $1,308
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!
Reviewed on Jun 18, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,918, price is now CA $1,396 per person
CA $1,396
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Close to a ton of great dining options. Nice staff
Reviewed on Jun 20, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,349, price is now CA $1,714 per person
CA $1,714
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.
Reviewed on Jun 20, 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 $193 per night from Jun 29 to Jun 30
CA $193
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,140 reviews)
"Complicated"
Reviewed on Jun 19, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $182 per night from Jun 29 to Jun 30
CA $182
CA $217 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,601 reviews)
"Our stay was amazing! Staff was very helpful!"
Reviewed on Jun 19, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jul 4 to Jul 5
CA $203
CA $232 total
Jul 4 - Jul 5
includes taxes & fees
8.8/10 Excellent! (2,681 reviews)
"The only thing that would have made it excellent was if they had a pool/spa."
Reviewed on Jun 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
Chicago By Night River and Lake Cruise
CA $69
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.
