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.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,152, price is now CA $855 per person
CA $855
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
very clean and friendly staff

Reviewed on Jun 18, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,102, price is now CA $1,251 per person
CA $1,251
per person
Jul 28 - Jul 31
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,371, price is now CA $913 per person
CA $913
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
No drinking glasses in my room. No pen/pencil and paper

Reviewed on Jun 22, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,029, price is now CA $1,412 per person
CA $1,412
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views

Reviewed on Jun 22, 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $1,290, price is now CA $958 per person
CA $958
per person
Sep 14 - Sep 17
found 7 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (622 reviews)
James at the front desk was absolutely incredible. It was a quick stay due to storms in the area, but James' professionalism and care added some positivity to an otherwise stressful travel experience.

Reviewed on Jun 22, 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 $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! (10,163 reviews)
"The room was very clean and the staff were fantastic! I would recommend this hotel to anyone it was close to all the public transit stations"

Reviewed on Jun 22, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 6 to Jul 7
CA $197
CA $235 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,461 reviews)
"A very easily accessible location, close to many eateries and especially the magnificent mile!"

Reviewed on Jun 22, 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jun 30 to Jul 1
CA $178
CA $211 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,612 reviews)
"I just expected more from a 4 star. Downstairs bar was closed and the rooftop wasn’t as big as the pics portrayed it to be"

Reviewed on Jun 22, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,984 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
A coastal cityscape with high-rise buildings, a marina, and a park area.

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 $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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 Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $69
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
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.