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.
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 $1,601, price is now CA $1,042 per person
CA $1,042
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,458 reviews)
No restaurant or available food after 10pm.

Reviewed on Apr 21, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,872, price is now CA $1,722 per person
CA $1,722
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,266 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on Apr 22, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,237, price is now CA $1,387 per person
CA $1,387
per person
Jun 9 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on Apr 23, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,186, price is now CA $1,455 per person
CA $1,455
per person
Jun 4 - Jun 7
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (466 reviews)
Eric and the rest of the staff was very helpful from check in to check out! The place is very lovely!!!!! Would come back again soon!

Reviewed on Apr 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $4,651, price is now CA $3,155 per person
CA $3,155
per person
Jun 5 - Jun 12
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Great staff, facilities, esp the fitness & spa

Reviewed on Apr 23, 2026

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Oak Park Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
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! (10,128 reviews)
Great price for the location. Common areas are beautiful. The rooms are ok. One of the staff members was great. She went out of her way to help and offer suggestions. The rest of the staff we encountered were hard to find and not particularly motivated to be helpful. It took 30 minutes to get someone ...

Reviewed on Apr 24, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $162 per night from May 25 to May 26
CA $162
CA $192 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,120 reviews)
Wonderful and helpful sstaff. Excellent location

Reviewed on Apr 24, 2026

River Hotel
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 Apr 29 to Apr 30
CA $118
CA $180 total
Apr 29 - Apr 30
includes taxes & fees
8.2/10 Very Good! (2,633 reviews)
Great location, staff and value for money

Reviewed on Apr 24, 2026

Hotel Felix River North/Magnificent Mile
See all 5,085 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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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
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.