Parkside Vacations from $390
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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $664, price is now $390 per person
$390
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The staff was the best part of the hotel, accommodating, polite and patient. Rooms were so so but they offer so many amenities that is more than makes up for it
Reviewed on Apr 14, 2026
Baymont By Wyndham Schaumburg Chicago Northwest
Save 100% on your flight
Price was $897, price is now $464 per person
$464
per person
May 18 - May 22
found 16 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
No reviews
Everyone was nice, room was what i expected, and the late checkout policy was helpful and clear and easy to approach.
Reviewed on Apr 11, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $864, price is now $460 per person
$460
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Great stay! Loved to come back. Friendly staff!
Reviewed on Apr 13, 2026
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,066, price is now $569 per person
$569
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
They need to update the lobby real bad. Location is convenient a short walk to Willis Tower and you can self park very close.
Reviewed on Apr 3, 2026
Level Chicago – Old Town
Downtown Chicago
Price was $1,613, price is now $917 per person
$917
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 2026
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
$76 nightly
The price is $84 total per night from Apr 29 to Apr 30
$84 total
Apr 29 - Apr 30
Total with taxes and fees
7.2/10 Good! (1,515 reviews)
The hotel was very clean. Staff was nice. There is no elevator for those that can’t do stairs. However the stairs are small enough that it is not difficult I wish that they had soap that was bigger than a dime and even a box of tissue wouid be nice.
Reviewed on Apr 13, 2026
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 Apr 29 to Apr 30
$67 total
Apr 29 - Apr 30
Total with taxes and fees
6.4/10 (1,091 reviews)
It took 2 weeks of me calling to get my deposit back. They kept telling me it was sent just wait and I would wait and it would never come so I call back and they tell me the exact same thing. They will try so hard to not refund your deposit. Also the rooms are disgusting. They smell terrible and ...
Reviewed on Apr 14, 2026
Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $140 total per night from Apr 21 to Apr 22
$140 total
Apr 21 - Apr 22
Total with taxes and fees
8.4/10 Very Good! (1,285 reviews)
Our shower didn’t work. We went swimming and I couldn’t shower before my appointment. Vary disappointing. Won’t be back. Wish I had a refund of some sort.
Reviewed on Apr 14, 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
Wrigley Field
4.5/5(2,150 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(4,926 reviews)
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
98% 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.