Lower West Side Vacations from $439

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$439
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$853
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$632
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Staff was very friendly and provided great service. Very clean. Great location. Breakfast was great.

Reviewed on Oct 15, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$630
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$704
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (532 reviews)
The stay was all good as represented on the site!

Reviewed on Oct 12, 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 busy city street with tall buildings, a bus, and cars.

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.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Find hotels in Lincoln Park

Lower West Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
$126 total
Nov 11 - Nov 12
Total with taxes and fees
Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
$181 total
Nov 1 - Nov 2
Total with taxes and fees
River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$142 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
The Chicago Hotel Collection - Magnificent Mile
See all 4,773 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.
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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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Radius - Chicago

You can make plans for a show at Radius - Chicago during your trip to Chicago. Experience the area's art scene and festivals.
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The Geraghty

After visiting The Geraghty, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
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Canalport Riverwalk Park

After visiting Canalport Riverwalk Park, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
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St Pius Church

After visiting St Pius Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
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Chicago Art Department

After visiting Chicago Art Department, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
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Simone's

Simone's is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the area's art scene and festivals.
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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
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
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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.