Parkside Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,075
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.

Reviewed on Oct 2, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
CA $2,564
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class

Reviewed on Oct 1, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
CA $1,199
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
I stayed in a room at the back, every morning at 5:30 am trucks and dumpsters were moved, noise so loud it woke me up. Was charged an amenity fee and there were really mo amenities. Breakfast sucked both days in first floor restaurant. Won't stay again.

Reviewed on Oct 1, 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on Sep 24, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,111
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.4/10 Exceptional! (179 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.

Find hotels in Downtown 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.

Find hotels in Magnificent Mile
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.

Find hotels in The Loop
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.

Find hotels in River North
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.

Find hotels in Lincoln Park

Parkside Hotel Deals

Chicago Club Inn & Suites

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
CA $74
CA $82 total
Nov 1 - Nov 2
includes taxes & fees
7.2/10 Good! (1,842 reviews)
"Good deal for jetted tub room. Quite far from downtown but still close to local amenities. Gas station within 2 minute walking distance."

Reviewed on Oct 2, 2026

Chicago Club Inn & Suites
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $133
CA $156 total
Nov 1 - Nov 2
includes taxes & fees
Sleep Inn Midway Airport Bedford Park
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL
CA $192
CA $226 total
Nov 3 - Nov 4
includes taxes & fees
7/10 Good! (1,000 reviews)
"Everything was clean they are busy updating this hotel. I like to location close to the hospital and free parking."

Reviewed on Oct 1, 2026

Chicago Lake Shore Hotel
See all 993 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Parkside vacation package cost?
Customize your Parkside package from a low CA $1,075. 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

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.