Parkside Vacations from ₩589,714

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Parkside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩961,022, price is now ₩589,714 per person
₩589,714
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,747,949, price is now ₩1,040,990 per person
₩1,040,990
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,623,004, price is now ₩983,945 per person
₩983,945
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,012,408, price is now ₩625,567 per person
₩625,567
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on Oct 7, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩2,495,140, price is now ₩1,584,500 per person
₩1,584,500
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
We have stayed at every luxury property in Chicago and when coming to visit we always stay at the Park Hyatt. The rooms are spectacular!

Reviewed on Oct 10, 2025

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
Downtown Chicago showing a city

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.

Find hotels in Downtown Chicago

Parkside Hotel Deals

Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
The price is ₩103,064 per night from Oct 13 to Oct 14
₩103,064
₩114,376 total
Oct 13 - Oct 14
includes taxes & fees
7/10 Good! (1,267 reviews)
"Very good location, convenient to Oakbrook shopping center and West Suburbs. Great value"

Reviewed on Oct 6, 2025

Chicago Club Inn & Suites
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway, Willowbrook, IL
Fully refundableReserve now, pay when you stay
The price is ₩86,689 per night from Oct 19 to Oct 20
₩86,689
₩97,074 total
Oct 19 - Oct 20
includes taxes & fees
6.2/10 (1,007 reviews)
"My go-to place in the area. Decor is somewhat dated and check-in is slow sometimes yet I come back because it’s a convenient location and the prices are reasonable. I prefer a 1st floor room and the staff will usually honor the request if they can."

Reviewed on Sep 27, 2025

Red Roof Inn PLUS+ Chicago - Willowbrook
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
6540 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩167,741 per night from Nov 9 to Nov 10
₩167,741
₩197,070 total
Nov 9 - Nov 10
includes taxes & fees
8.4/10 Very Good! (1,251 reviews)
"Good AC Breakfast was minimal at best. Overall, pretty soulless"

Reviewed on Oct 8, 2025

Hampton Inn by Hilton Chicago-Midway Airport
See all 1,148 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 ₩589,714. 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.

Discover the most popular places to visit in Parkside

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

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