Parkside Holidays from AU$3,752

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Your Parkside Holiday

Parkside is beckoning! Whatever type of getaway you're planning, you can immerse yourself in the best of this neighbourhood with a Parkside holiday package. Give yourself enough time to get to leading nearby attractions like George Dunne National Golf Club during your trip to Parkside. No matter your travel plans or budget, booking the ultimate Parkside holiday is easy with Expedia.

Top Holiday Package Deals in Parkside

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

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
9 July - 16 July
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Nice property, great location. Hotel was a little grungier than the pics online make it seem and the rooms are quite small, but still clean. Staff was pleasant, not overly welcoming. Fantastic dog friendly option. Would stay here again.

Reviewed on 26 May 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
9 July - 16 July
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,600 reviews)
Great staff and excellent service

Reviewed on 26 May 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
9 July - 16 July
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
No reviews
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
9 July - 16 July
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (313 reviews)
Amazing views and comfortable rooms. Amenities were excellent.

Reviewed on 20 May 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
9 July - 16 July
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (3,404 reviews)
Always a great stay!

Reviewed on 24 May 2025

Our guide on where to stay in Parkside

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

Downtown Chicago

5 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 Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Our pick of the best Parkside Hotel Deals

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
3.5 out of 5
6201 Joliet Rd, Countryside, IL
Fully refundable
The price is AU$178 per night from 4 June to 5 June
AU$178
includes taxes & fees
4 June - 5 June
7.6/10 Good! (1,010 reviews)
"Overall our stay was really nice and our room had everything we needed and everything was clean. The only issue was that the doors to the other rooms often slammed shut waking me up."

Reviewed on 27 May 2025

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
Sleep Inn Midway Airport Bedford Park
Sleep Inn Midway Airport Bedford Park
2.5 out of 5
6650 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 29 May to 30 May
AU$178
includes taxes & fees
29 May - 30 May
7.6/10 Good! (1,476 reviews)
"Perfect in every way. Easy transport to and from airport. Great compl"

Reviewed on 26 May 2025

Sleep Inn Midway Airport Bedford Park
Hilton Chicago/Oak Lawn
Hilton Chicago/Oak Lawn
3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
The price is AU$282 per night from 3 June to 4 June
AU$282
includes taxes & fees
3 June - 4 June
8/10 Very Good! (1,002 reviews)
"Staff is lovely. I really enjoyed my stay!"

Reviewed on 20 May 2025

Hilton Chicago/Oak Lawn
See all 1,037 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Parkside holiday package cost?
Customize your Parkside package from a low AU$3,752. 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 holiday 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 holiday.
Where should I stay in Parkside?
If you want to be in the thick of things, stay somewhere close to Hollywood Casino Amphitheatre. Many travellers book a hotel around this famous attraction.
How far in advance should I book my Parkside holiday?
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 favourite 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 holiday is only clicks away.
Can I choose my airline with a Parkside Expedia holiday 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 holiday 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

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Six Flags Great America featuring rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Activities

River tour boat in Chicago

Architecture River Tour

AU$76
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$38
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.