Parkside Vacations from ￥290,705
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The Latest Parkside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
￥294,278
per person
Nov 11 - Nov 16
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
A word of warning to others looking to book this hotel. My family and I booked the Old Town location for 3 nights, specifically because of plans we had in that neighborhood and its proximity to the Red/Purple lines for other plans on the far Northside and Evanston. We had opted not to rent a car because of this.
On the MORNING of check-in (as we were boarding our flight to Chicago) I got an email that they could no longer honor our reservation, and they had rebooked us at the Fulton Market location. While they offered to upgrade our suite and refund a small amt of the nightly rate to help with Uber costs, the new location was a huge inconvenience. We couldn't use the CTA as planned and ended up spending quite a bit more $ on Uber than we were compensated for. We also lost a lot of time in transit that we could have spent enjoying our limited time in the city.
While the suite and building amenities are nice, the whole situation was extremely frustrating and disappointing. We would have cancelled the reservation and booked another hotel in a more convenient location if they had given us any advance notice.
A couple of other notes of warning - there was no housekeeping for the 3 days we were there. There was also a Nespresso maker with 4 pods when we arrived, but when we asked for more the next day, they said we had to pay for them. Given how high the nightly rates are for this hotel it's surprising that no daily housekeeping nor coffee is provided.
Reviewed on Sep 16, 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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Parkside Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
￥23,580
￥29,231 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Na"
Reviewed on Sep 16, 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
￥10,690
￥11,864 total
Oct 18 - Oct 19
includes taxes & fees
7.2/10 Good! (1,805 reviews)
"This place not a 5 star hotel but it was really nice and I would definitely stay there again. It was close to a lot of things. The service was great. Free breakfast was also good."
Reviewed on Sep 16, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
￥26,240
￥30,803 total
Sep 20 - Sep 21
includes taxes & fees
7/10 Good! (1,005 reviews)
"Great location. Very clean-looks refurbished. The staff is amazing-very helpful & they try to help you have a good experience!"
Reviewed on Sep 15, 2026
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 ￥290,705. 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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,453
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,886
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.