
South Shore Vacations
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Price found within the past 48 hours. Click for updated prices.
- Hotel Felix River North/Magnificent Mile
Jul 1 - Jul 6Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago5 nights8.2/10 - Very Good (2,742 reviews)Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop¥351,570¥300,654found 1 day agoper traveler - Hotel Riu Plaza Chicago
Jul 1 - Jul 6Hotel Riu Plaza Chicago + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (4,314 reviews)"Great clean room, staff were so nice!"Reviewed June 1, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop¥413,302¥326,616found 1 day agoper traveler - Swissotel - Chicago
Jul 1 - Jul 6Swissotel - Chicago + Flight
Downtown Chicago5 nights9.0/10 - Wonderful (3,364 reviews)"The gym is on 43 floor.. amazing"Reviewed May 31, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop¥377,793¥307,578found 1 day agoper traveler - The Langham, Chicago
Jul 1 - Jul 6The Langham, Chicago + Flight
Downtown Chicago5 nights9.8/10 - Exceptional (1,002 reviews)"Ask for a water view!"Reviewed May 31, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop¥491,549¥413,830found 1 day agoper traveler - Kimpton Gray Hotel by IHG
Jul 1 - Jul 6Kimpton Gray Hotel by IHG + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (1,001 reviews)"Great hotel. Loved the lobby and our room. Would definitely stay here again."Reviewed May 19, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop¥397,201¥340,096found 1 day agoper traveler
Where to stay in South Shore
Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore

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.
South Shore Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥22,218 per night from Jun 29 to Jun 30
¥22,218
¥26,415 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,143 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."
Reviewed on May 31, 2026

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is ¥24,209 per night from Jun 28 to Jun 29
¥24,209
¥28,783 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,498 reviews)
"Everything was great"
Reviewed on May 31, 2026

Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥30,104 per night from Jun 30 to Jul 1
¥30,104
¥40,329 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,312 reviews)
"The room and bathroom were very clean. The hotel staff is very hospitable and attentive. This hotel will definitely be my go to place to stay in Chicago!"
Reviewed on Jun 1, 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.
Frequently asked questions
Discover the most popular places to visit in South Shore

Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Michigan Avenue
4.5/5(336 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.
Things to do

Skydeck - Willis Tower Admission
¥6,904
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















