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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on Apr. 14, 2024

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 30 - Jun. 3
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (166 reviews)
I love the design of the residence hallway

Reviewed on Apr. 21, 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 30 - Jun. 3
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (636 reviews)
Did not seem well kept. The room was okay. Room service did not replenish enough towels... they should know how many guests are staying in the room and we had to ask for additional towels since there was the three of us. Front desk was very responsive and friendly. Loved the coffee bar downstairs. Easy walk to all venues outside of the hotel.

Reviewed on Apr. 14, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 8 - Jul. 11
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Amazing. Definitely coming back!

Reviewed on Apr. 20, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The staff are thoughtful and provide the best service. While I was there, I was already planning to come back and stay there again!

Reviewed on Apr. 24, 2024

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

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Parkside Hotel Deals

Holiday Inn Chicago – Midway Airport S, an IHG hotel
Holiday Inn Chicago – Midway Airport S, an IHG hotel
2.5 out of 5
7353 S Cicero Avenue, Chicago, IL
Fully refundable
The price is CA $137 per night from Apr. 29 to Apr. 30
CA $137
CA $174 total
includes taxes & fees
Apr 29 - Apr 30
8.2/10 Very Good! (1,001 reviews)
"I liked MJ and Melton"

Reviewed on Apr. 22, 2024

Holiday Inn Chicago – Midway Airport S, an IHG hotel
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 CA $102 per night from Apr. 29 to Apr. 30
CA $102
CA $114 total
includes taxes & fees
Apr 29 - Apr 30
6/10 (1,001 reviews)
"Thank you for the services the personal very! helpful. I like also the store restaurant nearby, although the room could've been cleaned with scented cleaning product to make it a homier experience. Lastly the water pressure wasn't that strong but the staff were very kind."

Reviewed on Apr. 22, 2024

Chicago Club Inn & Suites
Jaslin Hotel
Jaslin Hotel
3 out of 5
261 West Cermak Rd, Chicago, IL
The price is CA $157 per night from Apr. 29 to Apr. 30
CA $157
CA $185 total
includes taxes & fees
Apr 29 - Apr 30
8.6/10 Excellent! (1,000 reviews)
"Location was really great! We could walk to all of the restaurants in Chinatown."

Reviewed on Apr. 22, 2024

Jaslin Hotel
See all 948 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Parkside vacation package cost?
Customize your Parkside package from a low CA $783. 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

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier

Things to do

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

CA $73
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $102
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

Other vacations you might like

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