Parkside Vacations from $404
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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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $768, price is now $404 per person
$404
per person
Mar 27 - Apr 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $842, price is now $462 per person
$462
per person
Mar 27 - Apr 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything is ok but no parking lot and too much fee
Reviewed on Jan 6, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $481 per person
$481
per person
Mar 27 - Apr 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,467, price is now $853 per person
$853
per person
Mar 27 - Apr 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $900, price is now $524 per person
$524
per person
Mar 27 - Apr 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 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 7 to Jan 8
$78 total
Jan 7 - Jan 8
Total with taxes and fees
7/10 Good! (1,396 reviews)
Everything was great
Reviewed on Jan 4, 2026
Motel 6 Bridgeview, IL
9625 S 76th Ave Bridgeview IL
Fully refundableReserve now, pay when you stay
$42 nightly
The price is $48 total per night from Jan 13 to Jan 14
$48 total
Jan 13 - Jan 14
Total with taxes and fees
7/10 Good! (1,349 reviews)
Ok
Reviewed on Jan 4, 2026
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
6201 Joliet Rd Countryside IL
Fully refundable
$91 nightly
The price is $102 total per night from Jan 30 to Jan 31
$102 total
Jan 30 - Jan 31
Total with taxes and fees
7.8/10 Good! (1,357 reviews)
Niceeeee
Reviewed on Jan 6, 2026
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
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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
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.