Lower West Side Vacations from $235
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Your Lower West Side Vacation
Discover the delights of Lower West Side with a tailor-made Lower West Side vacation package. From its history to its culture and beyond, this neighborhood offers plenty of opportunities for relaxation and fun. Your trip to Lower West Side wouldn't be complete without a visit to top attractions nearby such as University of Illinois Chicago, United Center and Anna and Frederick Douglass Park. Don't just dream it — make it happen! Reserve your perfect Lower West Side vacation with Expedia and experience travel your way.
The Latest Lower West Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was $1,440, price is now $428 per person
$428
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
My experience at the Sheraton was terrible. I was assigned a room right next to the elevator, where there was also a shared microwave for guests on the floor. A large group of young people was placed in the same hallway. They appeared to be intoxicated and made excessive noise from around 11 p.m. until nearly 4 a.m., making it impossible to sleep.
I called the front desk three times asking for help, but the noise continued and nothing was resolved. I felt very unsafe and completely let down by the hotel staff.
Guests should be able to expect a restful stay and a response when they ask for help. I left exhausted and deeply disappointed. I expected much better from the Sheraton.
Reviewed on Oct 28, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $648, price is now $377 per person
$377
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.
Reviewed on Oct 26, 2026
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $124 total per night from Nov 10 to Nov 11
$124 total
Nov 10 - Nov 11
Total with taxes and fees
8/10 Very Good! (10,062 reviews)
"Only feet from my conference at the Spertus Institute and walking distance to Grant Park."
Reviewed on Oct 30, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $159 total per night from Nov 3 to Nov 4
$159 total
Nov 3 - Nov 4
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $131 total per night from Nov 26 to Nov 27
$131 total
Nov 26 - Nov 27
Total with taxes and fees
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.
Stay near popular Lower West Side attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.