Parkside Vacations from ￥266,396

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The Latest Parkside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥333,099, price is now ￥266,396 per person
￥266,396
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
Overall great experience

Reviewed on Jun 15, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥369,264, price is now ￥305,394 per person
￥305,394
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.

Reviewed on Jun 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥443,444, price is now ￥366,781 per person
￥366,781
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,888 reviews)
Very clean rooms, helpful staff and great amenities! Close to everything and convenient to shopping and eating Felt safe and comfortable in the area !

Reviewed on Jun 15, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was ￥444,968, price is now ￥369,419 per person
￥369,419
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,384 reviews)
The staff was very helpful! I arrive a bit early and the front desk staff was able to get me in early so I could rest. The room view was amazing and very clean and comfortable. Location was also great , lively and walking distance to everything I wanted to see. Would definitely stay again!

Reviewed on Jun 16, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥350,859, price is now ￥292,083 per person
￥292,083
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 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

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Parkside Hotel Deals

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 refundableReserve now, pay when you stay
The price is ￥19,479 per night from Jul 5 to Jul 6
￥19,479
￥24,471 total
Jul 5 - Jul 6
includes taxes & fees
8.2/10 Very Good! (1,037 reviews)
"It was ok"

Reviewed on Jun 15, 2026

Holiday Inn Chicago – Midway Airport S by IHG
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 ￥11,703 per night from Jul 1 to Jul 2
￥11,703
￥12,988 total
Jul 1 - Jul 2
includes taxes & fees
7.2/10 Good! (1,601 reviews)
"Not a place you want to stay"

Reviewed on Jun 15, 2026

Chicago Club Inn & Suites
William Tell Hotel MOD Collection by Sonesta

William Tell Hotel MOD Collection by Sonesta

3.5 out of 5
6201 Joliet Rd Countryside IL
Fully refundableReserve now, pay when you stay
The price is ￥17,635 per night from Jun 30 to Jul 1
￥17,635
￥19,748 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (1,507 reviews)
"Just be well prepared"

Reviewed on Jun 15, 2026

William Tell Hotel MOD Collection by Sonesta
See all 989 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.

Frequently asked questions

How much does a Parkside vacation package cost?
Customize your Parkside package from a low ￥266,396. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.