Parkside Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.

Price found within the past 48 hours. Click for updated prices.
  • Jun 27 - Jul 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (485 reviews)
    "Perfect stay"
    Reviewed May 20, 2026
    Roundtrip Toronto (YTZ) - Chicago (ORD)
    YTZ - ORDNonstop ORD - YYZNonstop
    CA $1,457
    CA $975
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Jun 27 - Jul 1

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,508 reviews)
    "The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay."
    Reviewed May 20, 2026
    Roundtrip Toronto (YTZ) - Chicago (ORD)
    YTZ - ORDNonstop ORD - YYZNonstop
    CA $1,870
    CA $1,271
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Jul 23 - Jul 26

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,126 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Roundtrip Toronto (YTZ) - Chicago (ORD)
    YTZ - ORDNonstop ORD - YTZNonstop
    CA $1,763
    CA $1,251
    per traveller
    found 1 day ago
    Pendry Chicago
  • Jun 27 - Jul 1

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (1,875 reviews)
    "Great experience! Would stay here agin"
    Reviewed May 18, 2026
    Roundtrip Toronto (YTZ) - Chicago (ORD)
    YTZ - ORDNonstop ORD - YYZNonstop
    CA $2,513
    CA $1,789
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Jul 10 - Jul 14

    Level Chicago - River North + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,020 reviews)
    "Great experience and shoutout to the front desk people when I checked in ! They were very accommodating and kind . "
    Reviewed May 20, 2026
    Roundtrip Toronto (YYZ) - Chicago (ORD)
    YYZ - ORDNonstop ORD - YYZNonstop
    CA $1,678
    CA $1,200
    per traveller
    found 1 day ago
    Level Chicago - River North

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside

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 CA $105 per night from Jun 4 to Jun 5
CA $105
CA $117 total
Jun 4 - Jun 5
includes taxes & fees
7.2/10 Good! (1,573 reviews)
"Stayed Friday-Monday in a room with a hot tub. The jets in the hot tub are extremely forceful. Water pressure strong in bathroom as well. Fridge and microwave good. Only one electric outlet near the bed. Kept hitting the metal frame of the bed when i got in and out of it which was annoying. Ice machine ..."

Reviewed on May 20, 2026

Chicago Club Inn & Suites
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundable
The price is CA $130 per night from May 27 to May 28
CA $130
CA $153 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (1,872 reviews)
"It needs to be more clean for sure breakfast was a boomer, ac bearly worked it definitely could be better"

Reviewed on May 20, 2026

Sleep Inn Midway Airport Bedford Park
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is CA $190 per night from May 24 to May 25
CA $190
CA $237 total
May 24 - May 25
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"it was ok"

Reviewed on May 19, 2026

Holiday Inn Chicago – Midway Airport S by IHG
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 . 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

Things to do

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