Downtown Skokie Vacations from ￥309,498
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The Latest Downtown Skokie Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was ￥421,916, price is now ￥309,498 per person
￥309,498
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥481,245, price is now ￥312,264 per person
￥312,264
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.
Reviewed on Feb 7, 2026
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥579,324, price is now ￥388,004 per person
￥388,004
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Pendry Chicago
Downtown Chicago
Price was ￥478,193, price is now ￥332,532 per person
￥332,532
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥543,532, price is now ￥396,136 per person
￥396,136
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Where to stay in Downtown Skokie
Find the best Downtown Skokie areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Skokie
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.
Downtown Skokie Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥14,032 per night from Feb 9 to Feb 10
￥14,032
￥16,472 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (9,853 reviews)
Friendly staff. Clean room.
Reviewed on Feb 5, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,788 per night from Feb 21 to Feb 22
￥21,788
￥30,191 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,610 reviews)
Good
Reviewed on Feb 7, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,115 per night from Feb 22 to Feb 23
￥16,115
￥18,917 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless
Reviewed on Feb 4, 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.
Discover the most popular places to visit in Downtown Skokie
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
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
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,883
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
￥6,341
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.