Parkside Vacations from $376
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $647, price is now $376 per person
$376
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room
Clean bathroom
Friendly staff
Reviewed on Jan 1, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $820, price is now $466 per person
$466
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Had a great dinner at Fora before a very short walk to the new years eve event we were headed to and then came back for a great night's sleep in a very comfortable room! All the staff we interacted with were great!
Reviewed on Jan 1, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,345, price is now $800 per person
$800
per person
Mar 14 - Mar 21
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Views were great balcony included but bed was uncomfortable
Reviewed on Dec 30, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,006, price is now $605 per person
$605
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.
Reviewed on Dec 31, 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
$70 nightly
The price is $78 total per night from Jan 3 to Jan 4
$78 total
Jan 3 - Jan 4
Total with taxes and fees
7/10 Good! (1,383 reviews)
Very clean room, property was safe.
Reviewed on Dec 29, 2025
Motel 6 Bridgeview, IL
9625 S 76th Ave Bridgeview IL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $67 total per night from Jan 28 to Jan 29
$67 total
Jan 28 - Jan 29
Total with taxes and fees
7/10 Good! (1,337 reviews)
Easy parking and a very clean hotel. Lots of options for food nearby
Reviewed on Dec 30, 2025
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
6201 Joliet Rd Countryside IL
Fully refundable
$87 nightly
The price is $97 total per night from Jan 5 to Jan 6
$97 total
Jan 5 - Jan 6
Total with taxes and fees
7.8/10 Good! (1,333 reviews)
Staff friendlyness. They are always accommodating.
Reviewed on Dec 25, 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
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.
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.
Things to do
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
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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.