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 $1,277, price is now CA $895 per person
CA $895
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
No reviews
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,769, price is now CA $1,239 per person
CA $1,239
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (395 reviews)
Great location and well maintained property!

Reviewed on May 29, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,060, price is now CA $1,471 per person
CA $1,471
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.

Reviewed on May 31, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $1,795, price is now CA $1,285 per person
CA $1,285
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Staff was amazing and very helpful, gave us a lot of great recommendations for places to check out and also upgraded our room for free. The room was very nice, a little tight but that is expected in Chicago. Bathroom was perfect great shower, amazing view from room and bathroom window. Very conveniently located, quick walk from the train. Highly recommend and would stay again

Reviewed on Jun 1, 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! (10,151 reviews)
"Booked through Expedia. Arrived and was told my booking was cancelled. I had no indication of this by Expedia. Ended up frantically looking for a room in Chicago in the middle of the night. Very bad experience"

Reviewed on Jun 1, 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! (1,505 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

4.5/5(159 reviews)

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

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

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.