
Lower West Side Vacations from ¥255,376
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The Latest Lower West Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was ¥295,904, price is now ¥255,376 per person
¥255,376
per person
Dec 23 - Dec 27
found 2 days ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.
Reviewed on Nov 18, 2025

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was ¥371,466, price is now ¥260,622 per person
¥260,622
per person
Dec 23 - Dec 27
found 2 days ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥402,036, price is now ¥316,946 per person
¥316,946
per person
Dec 23 - Dec 27
found 2 days ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on Nov 17, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥383,892, price is now ¥316,307 per person
¥316,307
per person
Dec 23 - Dec 27
found 2 days ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
19.2/10 Exceptional! (1,000 reviews)
Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!!
Reviewed on Nov 18, 2025

Level Chicago – Old Town
Downtown Chicago
Price was ¥330,520, price is now ¥277,395 per person
¥277,395
per person
Dec 23 - Dec 27
found 2 days ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
Where to stay in Lower West Side
Find the best Lower West Side areas and neighborhoods for the activities you enjoy most. Learn more about Lower West Side

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.
Lower West Side 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 ¥13,539 per night from Dec 10 to Dec 11
¥13,539
¥15,895 total
Dec 10 - Dec 11
includes taxes & fees
8.4/10 Very Good! (5,272 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.
Reviewed on Nov 19, 2025

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥16,424 per night from Nov 25 to Nov 26
¥16,424
¥23,161 total
Nov 25 - Nov 26
includes taxes & fees
8.4/10 Very Good! (2,065 reviews)
Classy and classic! Never disappoints
Reviewed on Nov 16, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥12,934 per night from Dec 7 to Dec 8
¥12,934
¥15,184 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,324 reviews)
Awesome location and valet was very helpful
Reviewed on Nov 18, 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
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.




