Parkside Vacations from $288
Book a Hotel + Flight or Car together to unlock savings
Your Parkside Vacation
Book a custom vacation package to Parkside and prepare to experience this city on your own terms. Think about spending some time in the neighborhood of Flossmoor, which is good for golfing and lots more. A trip to Parkside is an excellent opportunity to take in the sights. Be sure to stop by big-name attractions such as Hollywood Casino Amphitheatre, Odyssey Fun World and George Dunne National Golf Club. Expedia can help you escape the everyday. Tailor your vacation to Parkside to suit your style of travel, whatever that may look like.
The Latest Parkside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG
Half Day
per person
Oct 22 - Oct 27
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
In a great neighborhood. Quiet, clean. Excellent room layout. Free laundry was very nice to have. Nice breakfast.
Reviewed on Aug 14, 2025
Where to stay in Parkside
Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Parkside Hotel Deals
Chicago Club Inn & Suites
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Sep 16 to Sep 17
$80 total
Sep 16 - Sep 17
Total includes taxes and fees
7/10 Good! (1,234 reviews)
"I liked the accessibility to the pool."
Reviewed on Aug 9, 2025
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway, Willowbrook, IL
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Sep 15 to Sep 16
$66 total
Sep 15 - Sep 16
Total includes taxes and fees
6.2/10 (1,003 reviews)
"Chilis Target"
Reviewed on Aug 16, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
Fully refundable
$123 nightly
The price is $145 total per night from Aug 26 to Aug 27
$145 total
Aug 26 - Aug 27
Total includes taxes and fees
8.8/10 Excellent! (1,124 reviews)
Located right in the heart of Chinatown.
"Friendly staffs and fast services. Small room, but comfy bed and clean sheets. Located right in the heart of Chinatown. Lots of food choices within walking distance."
Reviewed on Aug 15, 2025
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.
Discover the most popular places to visit in Parkside
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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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.