Parkside Vacation Packages 2026 from $216

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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 Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$216

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (3,105 reviews)

Room small

Reviewed on Oct 12, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$362

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

The Riu was great. I especially liked their attention to low-energy use. And, yes, like other commenters stated, the breakfast was plentiful.

Reviewed on Oct 12, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$418

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$467

per person

Dec 18 - Dec 22

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,523 reviews)

Place was great in general 10/10 will be back

Reviewed on Oct 12, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$390

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,727 reviews)

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Parkside Hotel Deals

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL

Fully refundableReserve now, pay when you stay

$52 nightly

$58 total

Nov 11 - Nov 12

Total with taxes and fees

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Fully refundable

$149 nightly

$173 total

Oct 25 - Oct 26

Total with taxes and fees

8/10 Very Good! (1,011 reviews)

"I booked from the airport because there was a shuttle. That shuttle ended at 7pm so I had to pay for an uber. When I left the next morning, I needed yet another uber. There is no coffee in the lobby. No vending machines for soda or snacks. Aside from the lovely woman at check in, all staff were unresponsive. ..."

Reviewed on Oct 12, 2026

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

Fully refundable

$101 nightly

$119 total

Nov 2 - Nov 3

Total with taxes and fees

8/10 Very Good! (2,172 reviews)

"Staff were kind and friendly"

Reviewed on Oct 12, 2026

See all 1,018 properties in Parkside

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.