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 $1,183, price is now CA $826 per person
CA $826
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
The gym is on 43 floor.. amazing

Reviewed on May 31, 2026

Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Price was CA $2,463, price is now CA $1,671 per person
CA $1,671
per person
Aug 12 - Aug 16
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
No reviews
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 $1,701, price is now CA $1,168 per person
CA $1,168
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Great experience and beautiful views

Reviewed on Jun 1, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,515, price is now CA $1,060 per person
CA $1,060
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great and very elegant hotel! I absolutely loved it! The only thing is a little bit noisy but it’s the price you have to pay to be in an excellent location, you have everything you need in a walking distance. I would definitely stay here again.

Reviewed on May 30, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,358, price is now CA $969 per person
CA $969
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room Other than that the front desk and cleaning ladies was very nice.

Reviewed on May 29, 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 $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,152 reviews)
"The location is very good. The room is clean and quiet although the whole building is old. We did not have chance to use the air conditioner because the temperature is not high. It seems there is no heater in this room, so it was a bit cold in midnight."

Reviewed on Jun 2, 2026

Congress Plaza Hotel
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 $210 per night from Jun 28 to Jun 29
CA $210
CA $249 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,506 reviews)
"They cancelled my reservation without notifying Expedia or me and I had to find a new place to stay. They are the worst hotel ever. Do not stay here. Do not trust them. They even admitted that the reason they did it is because my rate that I booked at was too low."

Reviewed on Jun 2, 2026

The Chicago Hotel Collection - Magnificent Mile
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 $262 per night from Jun 30 to Jul 1
CA $262
CA $350 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,317 reviews)
"Good breakfast"

Reviewed on Jun 2, 2026

Hotel Riu Plaza Chicago
See all 5,026 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
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
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.