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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,481, price is now CA $945 per person
CA $945
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Great view of the room. The staff were always willing to help and to provide.

Reviewed on May 5, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,669, price is now CA $1,079 per person
CA $1,079
per person
Jun 28 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (105 reviews)
Such a cute hotel , reminded me of some I’ve stayed in in Europe !! And the location was perfect

Reviewed on May 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,911, price is now CA $1,252 per person
CA $1,252
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking

Reviewed on May 3, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,447, price is now CA $1,630 per person
CA $1,630
per person
Jun 27 - Jun 30
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (973 reviews)
Rooms were cleaned I liked how secure the hotel was.

Reviewed on Apr 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,789, price is now CA $1,211 per person
CA $1,211
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too

Reviewed on May 3, 2026

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Oak Park Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 25 to May 26
CA $118
CA $182 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,679 reviews)
The hotel Felix was perfect . Walking distance to everything I wanted to do . Friendly staff and great accommodations.

Reviewed on May 5, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $184 per night from May 26 to May 27
CA $184
CA $219 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,162 reviews)
Really nice rooms, and the staff was amazing!

Reviewed on May 5, 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from May 27 to May 28
CA $183
CA $256 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,057 reviews)
Beautiful and clean. Staff was very friendly and accommodating, The roof top bar was sunning!!

Reviewed on May 5, 2026

Hotel Riu Plaza Chicago
See all 5,034 properties in Oak Park
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.
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Discover the most popular places to visit in Oak Park

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Oak Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Oak Park

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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.