Chicago Vacations from ￥210,174
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥265,634, price is now ￥210,174 per person
￥210,174
per person
Nov 29 - Dec 3
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
The property is Great I got married there!
Reviewed on Sep 24, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥343,518, price is now ￥246,906 per person
￥246,906
per person
Nov 29 - Dec 3
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Clean rooms and friendly staff. Centrally located. Breakfast is a feast. One of the best hotel breakfasts I have experienced. Roof top bar has a terrific view of the City and perfect for an evening cocktail. They don't have their own parking. I think this is typical for downtown so I recommend figuring that out before you arrive.
Reviewed on Sep 24, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥399,230, price is now ￥289,662 per person
￥289,662
per person
Nov 29 - Dec 3
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again!
Reviewed on Sep 23, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥326,194, price is now ￥242,014 per person
￥242,014
per person
Nov 29 - Dec 3
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on Sep 21, 2025
The Emily Hotel
Downtown Chicago
Price was ￥304,646, price is now ￥239,497 per person
￥239,497
per person
Nov 29 - Dec 3
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead
Reviewed on Sep 22, 2025
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about 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 the Best Chicago Vacation Packages
Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,816 per night from Sep 29 to Sep 30
￥22,816
￥26,783 total
Sep 29 - Sep 30
includes taxes & fees
7.8/10 Good! (9,294 reviews)
"Location is perfect. Would definetly stay here again on my next trip to Chicago"
Reviewed on Sep 24, 2025
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥29,935 per night from Oct 25 to Oct 26
￥29,935
￥35,140 total
Oct 25 - Oct 26
includes taxes & fees
8.2/10 Very Good! (2,139 reviews)
"Great"
Reviewed on Sep 19, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is ￥26,558 per night from Oct 2 to Oct 3
￥26,558
￥31,176 total
Oct 2 - Oct 3
includes taxes & fees
8.4/10 Very Good! (3,958 reviews)
"Very good hotel"
Reviewed on Sep 23, 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.
Discover the most popular places to visit in Chicago
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.
What to do in Chicago
Wendella's 90-min Chicago River Architecture Tour
￥6,633
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
￥6,633
per adult
96% of travellers recommend
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