Lower West Side Vacations from $345
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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.
Four Seasons Hotel Chicago
Downtown Chicago
Price was $4,716, price is now $2,731 per person
$2,731
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Late on room service. Forgot items requested, making room service even later.
Tv was not plugged in correctly and wasted my time. If i pay this much for a room for 2 nights I really expect these simple things to work the first time and me not have to waste my time trying to figure out why the tv isnt working.
Idk i think some of the staff is a little confused or lazy im not sure. Beautiful hotel and beautiful room with a great view.
Also the wings from room service could be SOO muchh better. Thanks for taking all my money tho!
Reviewed on Aug 4, 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
$144 nightly
The price is $171 total per night from Aug 30 to Aug 31
$171 total
Aug 30 - Aug 31
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $181 total per night from Aug 16 to Aug 17
$181 total
Aug 16 - Aug 17
Total with taxes and fees
8/10 Very Good! (1,930 reviews)
"Always love staying at the ambassador! So much old charm but modern amenities and gorgeous design. Located in a lovely quiet neighborhood north of the loop with lots of walkable cafes and restaurants."
Reviewed on Aug 6, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $246 total per night from Aug 29 to Aug 30
$246 total
Aug 29 - Aug 30
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
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.