South Loop Vacations from ￥291,128
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The Latest South Loop Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥351,120, price is now ￥291,128 per person
￥291,128
per person
Jan 17 - Jan 21
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
FOOD WAS GOOD, JUST A LITTLE COLD, BUT NO MAJOR PROBLEMS
Reviewed on Nov 12, 2025
Pendry Chicago
Downtown Chicago
Price was ￥478,928, price is now ￥418,007 per person
￥418,007
per person
Jan 2 - Jan 8
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.
Reviewed on Nov 12, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥466,364, price is now ￥410,922 per person
￥410,922
per person
Jan 2 - Jan 8
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥464,252, price is now ￥415,319 per person
￥415,319
per person
Jan 2 - Jan 8
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Room was spotless on arrival and through our stay. Housekeeping Staff were all diligent and courteous. When our TV / internet connection stopped working, Jordan from maintenance solve the issue within minutes and took the time to explain the steps involved in case it happened again(it didn't). Room was spacious. Member services, concierge and reception staff were good. Overall a great experience. Only drawback was that one of the reasons we picked the hotel was to enjoy the rooftop patio views which were advertised as one of the best in the city... Unfortunately it was closed the entire length of our stay. I understand rooftop bar/food service was unavailable but access should have at least been granted, especially on the sunnier days.
Reviewed on Nov 12, 2025
Arlo Chicago
Downtown Chicago
Price was ￥456,322, price is now ￥412,413 per person
￥412,413
per person
Jan 2 - Jan 8
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We felt welcomed and supported in every way. Tasteful, artistic, comfortable, convenient, fun, good food. Terrific staff. Will definitely come again. Highly recommend.
Reviewed on Nov 12, 2025
Where to stay in South Loop
Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop
Downtown Chicago
4 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.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,565 reviews)
Place is great, super classic feel. Staff is super nice, very clean, comfortable bed. They upgraded me to a lakeview room which was amazing. Only thing I'll say is that it took a while for the water to warm up in the shower. It eventually did, though. Would definitely come back. Has that classic ...
Reviewed on Nov 12, 2025
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥16,296 per night from Nov 26 to Nov 27
￥16,296
￥23,651 total
Nov 26 - Nov 27
includes taxes & fees
8.4/10 Very Good! (2,289 reviews)
Easy access
Reviewed on Nov 10, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥13,226 per night from Nov 17 to Nov 18
￥13,226
￥15,528 total
Nov 17 - Nov 18
includes taxes & fees
7.2/10 Good! (2,453 reviews)
Friendly staff and clean room
Reviewed on Nov 11, 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 South Loop
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Adler Planetarium and Astronomy Museum
Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.
Columbia College Chicago
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the entertainment choices and notable monuments in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
￥6,717
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,749
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.