Parkside Vacations from $418
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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.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out
Reviewed on Jun 29, 2025
Dorothy's
Lakeview
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (47 reviews)
The area has a lot of fun nightlife and things to do, but it was surprisingly quiet in our room! The room itself was clean and felt quite private, despite being in the shared suite. All the other guests we met were kind and courteous too! We drove, and parking was somewhat difficult but the map provided showing parking rules for surrounding roads made that much easier! The only thing we didn’t love was the provided breakfast, my partner told me they would have loved for some sausage or eggs to be included.
Reviewed on Jun 15, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 18 - Aug 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on Jun 27, 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
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
6201 Joliet Rd, Countryside, IL
Fully refundable
$110 nightly
The price is $123 total per night from Jul 6 to Jul 7
$123 total
Jul 6 - Jul 7
Total includes taxes and fees
7.6/10 Good! (1,041 reviews)
"Was nice.... but pool being out of order was unexpected and a bummer. Staff not really apologetic about it either."
Reviewed on Jun 26, 2025
Motel 6 Bridgeview, IL
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
$50 nightly
The price is $56 total per night from Jul 14 to Jul 15
$56 total
Jul 14 - Jul 15
Total includes taxes and fees
6.8/10 (1,194 reviews)
"My remote for TV was avt up have hard charging andthe tv"
Reviewed on Jul 2, 2025
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway, Willowbrook, IL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $67 total per night from Jul 14 to Jul 15
$67 total
Jul 14 - Jul 15
Total includes taxes and fees
6.2/10 (1,011 reviews)
"There was no hot water one morning but it was fixed by the next dsy"
Reviewed on Jun 29, 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
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Michigan Avenue
4.5/5(332 reviews)
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.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
92% of travellers recommend
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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.