
Chicago Vacations from ¥247,106
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.

The Emily Hotel
Downtown Chicago
Price was ¥325,639, price is now ¥247,106 per person
¥247,106
per person
Dec 17 - Dec 24
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Always a great stay! Staff are great and rooms present great value.
Reviewed on Nov 1, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥327,890, price is now ¥254,830 per person
¥254,830
per person
Dec 9 - Dec 15
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
The staff here was super friendly and helpful! Loved how they decorated the lobby for Halloween. Overall a great hotel.
Reviewed on Nov 3, 2025


Level Chicago – Old Town
Downtown Chicago
Price was ¥341,248, price is now ¥270,727 per person
¥270,727
per person
Dec 9 - Dec 15
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom.
The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine.
Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters.
Reviewed on Oct 29, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥308,848, price is now ¥249,294 per person
¥249,294
per person
Dec 9 - Dec 15
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 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

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥18,194 per night from Nov 23 to Nov 24
¥18,194
¥21,358 total
Nov 23 - Nov 24
includes taxes & fees
8.4/10 Very Good! (5,187 reviews)
Phone is our room did not work but no one came to look at it.
Reviewed on Nov 3, 2025

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥14,448 per night from Nov 24 to Nov 25
¥14,448
¥16,960 total
Nov 24 - Nov 25
includes taxes & fees
7.8/10 Good! (9,668 reviews)
Friendly staff. Room is clean and nice.
Reviewed on Nov 3, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥15,576 per night from Nov 17 to Nov 18
¥15,576
¥18,284 total
Nov 17 - Nov 18
includes taxes & fees
8.8/10 Excellent! (3,220 reviews)
Great staff at the front desk!
Reviewed on Nov 2, 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
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.
What to do in Chicago

Skydeck - Willis Tower Admission
¥6,612
per adult
100% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
¥3,691
per adult
84% of travellers recommend
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