Parkside Vacations
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.
Price found within the past 48 hours. Click for updated prices.
- Level Chicago Fulton Market
Jul 10 - Jul 14Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (489 reviews)"Amazing place"Reviewed May 26, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop - Hotel Riu Plaza Chicago
Jul 31 - Aug 3Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights9.4/10 - Exceptional (4,288 reviews)"Staff was super nice and attentive."Reviewed May 29, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 31 - Aug 3Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights9.4/10 - Exceptional (2,512 reviews)"Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes."Reviewed May 28, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - Urban Chicago Oasis
Jul 23 - Jul 27Urban Chicago Oasis + Flight
Lakeview4 nightsRoundtrip • New York (LGA) - Chicago (MDW)LGA - MDW • Nonstop ORD - JFK • Nonstop - Swissotel - Chicago
Jul 31 - Aug 3Swissotel - Chicago + Flight
Downtown Chicago3 nights9.0/10 - Wonderful (3,356 reviews)"Staff was so helpful"Reviewed May 29, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop
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
$73 nightly
The price is $81 total per night from Jun 3 to Jun 4
$81 total
Jun 3 - Jun 4
Total with taxes and fees
7.2/10 Good! (1,564 reviews)
"I stayed there for several nights, and they never cleaned my room or checked in on me."
Reviewed on May 27, 2026
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Jun 5 to Jun 6
$73 total
Jun 5 - Jun 6
Total with taxes and fees
6.4/10 (1,124 reviews)
"Not Satisfied with the room."
Reviewed on May 29, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$159 nightly
The price is $187 total per night from Jun 3 to Jun 4
$187 total
Jun 3 - Jun 4
Total with taxes and fees
6.8/10 (1,001 reviews)
"Nice staff, clean, nice spot. Definitely will stay here the next time I’m in Chicago"
Reviewed on May 25, 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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
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.
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.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
96% 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.