Parkside Vacation Packages

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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.

Top Holiday Package Deals in Parkside

Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago

Downtown Chicago

CA $844

per person

Oct 30 - Nov 1

found 16 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,553 reviews)

Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested. Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them. Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.

Reviewed on Aug 26, 2026

Four Seasons Hotel Chicago

Downtown Chicago

CA $1,950

per person

Nov 5 - Nov 8

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,001 reviews)

Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.

Reviewed on Aug 23, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,940

per person

Nov 4 - Nov 8

found 7 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.6/10 Exceptional! (1,986 reviews)

隔音效果差

Reviewed on Aug 27, 2026

Kimpton Gray Hotel by IHG

Downtown Chicago

CA $983

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,008 reviews)

Kinzie Hotel

Downtown Chicago

CA $922

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (2,200 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 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 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 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

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

Fully refundableReserve now, pay when you stay

CA $86

CA $96 total

Sep 9 - Sep 10

includes taxes & fees

6.4/10 (1,261 reviews)

"Not a bad place but kind of old and run down. Strong smell of marijuana outside the rooms and in the staircases."

Reviewed on Aug 27, 2026

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Fully refundable

CA $158

CA $200 total

Sep 8 - Sep 9

includes taxes & fees

8.2/10 Very good! (1,003 reviews)

"The room was clean and cleaned daily accept the one day we were not out by 8 am. They never came back despite still being in the area cleaning other rooms. There is no Wi-Fi. The tv only gets digital aerial signals no cable no streaming. Whatever the room cost, add $23 per night for parking. No complimentary ..."

Reviewed on Aug 26, 2026

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL

Fully refundableReserve now, pay when you stay

CA $77

CA $86 total

Sep 27 - Sep 28

includes taxes & fees

See all 954 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.

Frequently asked questions

How much does a Parkside vacation package cost?

Customize your Parkside package from a low CA $844. Choose from any combination of flights, hotels and rental cars to craft the escape you've been dreaming about. Don't forget to add on a few experiences or activities!

How do I get a cheap travel package to Parkside?

Booking a Parkside vacation package with Expedia is such a simple way to save. We have over 550 air carriers and 1,000,000 hotels all over the world. With such a broad range to choose from, you'll have no hassles putting together your dream vacation.

Where should I stay in Parkside?

If you want to be in the thick of things, stay somewhere close to Hollywood Casino Amphitheatre. Many travelers book a hotel around this famous attraction.

How far in advance should I book my Parkside vacation?

While prices change frequently, we generally advise booking your seats as soon as possible. Most international fares become available on Expedia up to a year in advance. If circumstances have left you booking last minute, you may still get lucky. Discount prices to Parkside sometimes occur in the weeks prior to departure.

What does an Expedia Parkside travel package include?

Hotels, car rentals and flights — we bring you the very best bargains. All you have to do is select your favorite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an amazing Parkside trip.

What should I know before booking a Parkside travel package?

Find deals that suit your budget with an Expedia package. Hotels, flights, rental cars — we have them all. You'll save precious cash just for bundling your bookings. Whether you're going on an adventure in the snow or kicking back on a warm beach, your dream vacation is only clicks away.

Can I choose my airline with a Parkside Expedia vacation package?

Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to take your pick of available flights, hotels and activities that suit you.

If I'm not able to travel, can I cancel my Parkside vacation package?

If your travel plans in Parkside have changed, it's good to know that it's possible to cancel your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may impose fees. To find out more, check our Customer Service Portal.

Things to do

360 CHICAGO Observation Deck

CA $38

per adult

86% of travellers recommend

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34

per adult

90% of travellers recommend

Wendella's Lake and River Architecture Tour

CA $63

per adult

94% of travellers recommend

See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Parkside Vacation

Top Holiday Package Deals in Parkside

Swissotel - Chicago

Four Seasons Hotel Chicago

Trump International Hotel & Tower Chicago

Kimpton Gray Hotel by IHG

Kinzie Hotel

Where to stay in Parkside

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Parkside Hotel Deals

Red Roof Inn PLUS+ Chicago - Willowbrook

Holiday Inn Chicago – Midway Airport S by IHG

Chicago Club Inn & Suites

Frequently asked questions

Things to do

360 CHICAGO Observation Deck

Chicago: Navy Pier Centennial Wheel Ticket

Wendella's Lake and River Architecture Tour