Oak Park Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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
Level Chicago Fulton Market
La Banque Hotel
Chicago Athletic Association, a Hyatt Hotel
Hotel Arista

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.