Parkside Holidays
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Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
€585
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
7.8/10 Good! (1,886 reviews)
Came in on a Sunday and met the wonderful and incredibly helpful Raymond. He was super friendly and accommodating. The hotel had erroneously taken a $330 payment from my credit card that i had on file even though I had prepaid in full, and while it was set to refund back to my card it still left me $300 down. Raymond gave us an early check-in and an extra drink ticket as a small compensation for the inconvenience. Other notably nice employees were the rooftop bartender and the breakfast staff.
Unfortunately, most of the rest of the staff was borderline rude. There was one night we came in and asked about our free waters for the day, and the receptionist(not raymond this time) sighed heavily and handed us a bag of waters without saying a word. We thanked him and he didn’t even glance up at us or reply.
Issues i had with the room: not the cleanest bathroom, only one roll of toilet paper was in the room of 4 people, the shower head had a bad leak and the water pressure felt like a drizzle of rain. It also didn’t get or stay very hot, which I’ve never experienced at a hotel. The bed also didnt have fitted sheets on it, so if you wanted to sleep under the blankets you were just on the mattress.
Things I liked about the room: mini fridge, microwave, decent view. They do offer free water bottles each day of your stay, you just have to ask for them at the desk. There were no surprise fees at the end, just the one unfortunate error made the day of arrival, which they did refund.
Reviewed on 19 Aug 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
€594
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,942 reviews)
You have to check out the bar at the Whitehall!!!!
Ricky (the BEST bartender ever) was a lot of fun. Our plans were to go to the hotel bar for a quick drink and head out to dinner. We ended up spending all evening there; He kept the crowd there and made the best drinks. Just a fun time for all. We will be going back just to repeat the experience.
Reviewed on 19 Aug 2026
Where to stay in Parkside
Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Parkside
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
€61
27 Aug - 28 Aug
includes taxes & fees
6.4/10 (1,253 reviews)
"I stayed one (1) night of a 3 night booking. Room lighting was 50% functional, over the bathroom sink was 100% out. Bed was comfortable but the shower pooled water (didn’t fully drain) and the overall condition of the room was sub par. I attempted to get a refund for remaining nights, was promised ..."
Reviewed on 18 Aug 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
€124
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,023 reviews)
"I had the most comfortable stay here, the front desk was so kind and generous every time I called asked for anything I am so grateful to them for making my stay so nice, I never do reviews but this was my birthday weekend and they went above and beyond"
Reviewed on 19 Aug 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
€54
17 Sept - 18 Sept
includes taxes & fees
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 holiday package cost?
Customize your Parkside package from a low €585. 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.