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.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,988, price is now CA $1,184 per person
CA $1,184
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on May 16, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,256, price is now CA $1,425 per person
CA $1,425
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.
Reviewed on May 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,157, price is now CA $1,431 per person
CA $1,431
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Great view and room was very clean!
Reviewed on May 17, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,893, price is now CA $1,935 per person
CA $1,935
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (984 reviews)
We loved the view from the 30th floor! The place was near the L, bus stops and walking distance to restaurants.. The bed was comfortable but it would be nice to have a table and lamp on both sides. The room seemed to be geared towards singles rather than couples. The espresso machine was a nice touch but fairly unusable for us. We ended up buying instant coffee and used the electric kettle. Sad that we couldn’t use the hot tub during our trip because it was closed for maintenance. But all in all, we were quite pleased with the apartment! Hubby spent a lot of time on the balcony enjoying the views. Highly recommend!
Reviewed on May 16, 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 $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,141 reviews)
Did not look like the pictures shown online old hotel not update
Reviewed on May 17, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from May 25 to May 26
CA $194
CA $270 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,171 reviews)
Room was clean and the bed was comfortable. Housekeeping rummaged through my bag and my husbands suitcase. Nothing was taken (there was nothing of value) but they did not leave my things the way we purposely left them. Also didn’t appreciate staff sweeping right up to my breakfast chair to get me ...
Reviewed on May 17, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,424 reviews)
Great stay
Reviewed on May 17, 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
Skydeck - Willis Tower Admission
CA $60
per adult
96% 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.
