Parkside Vacation Packages 2026 from $322

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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 Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$322

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,274 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$463

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

Staff was very friendly and provided great service. Very clean. Great location. Breakfast was great.

Reviewed on Oct 15, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$439

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$749

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (532 reviews)

The stay was all good as represented on the site!

Reviewed on Oct 12, 2026

Sports Illustrated Resorts Chicago

Downtown Chicago

Save 100% on your flight

$425

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (1,489 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

$64 nightly

$71 total

Nov 15 - Nov 16

Total with taxes and fees

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Fully refundable

$145 nightly

$168 total

Nov 1 - Nov 2

Total with taxes and fees

8.2/10 Very Good! (1,006 reviews)

"The shuttle is an issue. Waited an hour for pickup at the Midway train station. The driver lied and said that he arrived and there was no one to pick up. Complete lie."

Reviewed on Oct 15, 2026

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

Fully refundable

$101 nightly

$119 total

Nov 8 - Nov 9

Total with taxes and fees

8/10 Very Good! (2,163 reviews)

"The carpet in the room has a terrible smell"

Reviewed on Oct 14, 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.