Lower West Side Vacations from $350

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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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $562, price is now $350 per person
$350
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,390, price is now $871 per person
$871
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $910, price is now $574 per person
$574
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,089, price is now $725 per person
$725
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
The location of this hotel is great with the exception of its proximity to the train tracks. There were train horns sounding at all hours and fairly frequently. The hot water in my room took an extremely long time and house keeping didn’t always replenish/ replace items they would remove such as dark face cloth for makeup removal and wet makeup removal towelette.

Reviewed on Nov 10, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $510, price is now $355 per person
$355
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Great buffet breakfast and friendly staff

Reviewed on Nov 11, 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
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Lower West Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 22 to Nov 23
$127 total
Nov 22 - Nov 23
Total with taxes and fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 12 to Nov 13
$138 total
Nov 12 - Nov 13
Total with taxes and fees
8/10 Very Good! (2,697 reviews)
"Excellent stay! Will definitely seek this property out again for my stay in Chicago"

Reviewed on Nov 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$101 nightly
The price is $120 total per night from Nov 23 to Nov 24
$120 total
Nov 23 - Nov 24
Total with taxes and fees
River Hotel
See all 4,609 properties in Lower West Side
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Stay near popular Lower West Side attractions

National Museum of Mexican Art

You can spend time exploring the galleries in National Museum of Mexican Art during your travels in Chicago. Experience the fascinating museums and acclaimed theater scene in this vibrant area.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

$24
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.