Parkside Vacations from ￥288,510
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The Latest Parkside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Transport access walking distance to take train to midway airport was easy and convenient
Reviewed on Aug 7, 2025
Level Chicago - River North
Downtown Chicago
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on Jul 27, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.
Reviewed on Aug 9, 2025
Where to stay in Parkside
Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
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.
Parkside Hotel Deals
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
Fully refundable
The price is ￥17,152 per night from Sep 2 to Sep 3
￥17,152
￥20,134 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,105 reviews)
"Room was comfortable and clean. But wish there was on site parking"
Reviewed on Aug 7, 2025
Chicago Club Inn & Suites
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
The price is ￥10,046 per night from Sep 7 to Sep 8
￥10,046
￥11,150 total
Sep 7 - Sep 8
includes taxes & fees
6.8/10 (1,247 reviews)
"Great everything"
Reviewed on Aug 7, 2025
Motel 6 Bridgeview, IL
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
The price is ￥7,976 per night from Aug 20 to Aug 21
￥7,976
￥8,932 total
Aug 20 - Aug 21
includes taxes & fees
6.8/10 (1,198 reviews)
Saved
"Staff was super helpful and made us feel welcomed after checking out of another motel in the area."
Reviewed on Aug 4, 2025
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
Discover the most popular places to visit in Parkside
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Chicago Sightseeing River and Lake Cruise
￥6,646
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.