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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,125, price is now CA $689 per person
CA $689
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean rooms, excellent shower, but most importantly the best, friendly, helpful staff. Really enjoyed our stay.

Reviewed on Feb 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,955, price is now CA $1,149 per person
CA $1,149
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,406, price is now CA $853 per person
CA $853
per person
Apr 23 - Apr 28
just found
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,317, price is now CA $951 per person
CA $951
per person
May 5 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.

Reviewed on Feb 26, 2026

Hotel Arista

Hotel Arista

4.5 out of 5
Price was CA $1,065, price is now CA $785 per person
CA $785
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Room was great, staff service was also great !!

Reviewed on Feb 20, 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 $122 per night from Feb 28 to Mar 1
CA $122
CA $143 total
Feb 28 - Mar 1
includes taxes & fees
8/10 Very Good! (9,888 reviews)
Kind staff and a nice view of the city, close to a ton of things in the area!

Reviewed on Feb 26, 2026

Congress Plaza 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 $175 per night from Mar 4 to Mar 5
CA $175
CA $244 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,418 reviews)
Clean rooms, excellent shower, but most importantly the best, friendly, helpful staff. Really enjoyed our stay.

Reviewed on Feb 26, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Mar 5 to Mar 6
CA $135
CA $158 total
Mar 5 - Mar 6
includes taxes & fees
8.6/10 Excellent! (5,687 reviews)
Great suite, friendly breakfast staff

Reviewed on Feb 26, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,124 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 featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

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

Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
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.