Lower West Side Vacations from $635

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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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$635
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$1,028
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The hotel was great! I was impressed by the cleanliness of the main areas and our room. Everything looked new and well maintained. The room was not overly large but it was very comfortable and well appointed. And…for the first time ever, there were plenty of hangers!! The staff were all very nice and helpful. I must also mention the buffet breakfast. It was amazing! I had read many glowing reviews about it and they were all true. Efficient staff, very clean and the food was always plentiful and hot. And again, for the first time, their coffee was excellent (never found a hotel that served good coffee until now). The one thing I was disappointed with was the rooftop bar. After supper one night we decided to go for a drink. Could not find a seat because they were all reserved but nobody was sitting in any of them! They were not very helpful and so we left.

Reviewed on Sep 26, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$713
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
$1,061
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Gorgeous!! Highly recommend the 1 BR suite!

Reviewed on Sep 25, 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
Save 100% on your flight
$910
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,077 reviews)

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.

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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.

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Lower West Side Hotel Deals

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
$186 nightly
$221 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (5,446 reviews)
"No view whatsoever, tried to get an upgrade, no luck …"

Reviewed on Sep 26, 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$157 nightly
$187 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (10,232 reviews)
"I booked a room with a bathtub, to find out that management allegedly is taking out all of the bathtubs. The room was tiny. It looked like they tried to maintain some of the early charm and details in the room but landlord special style. The entire place smelled old and musty. The bed was comfortable ..."

Reviewed on Sep 26, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$170 nightly
$202 total
Sep 27 - Sep 28
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 4,645 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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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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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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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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Mexican Fine Arts Center Museum

You can spend an afternoon studying the exhibits at Mexican Fine Arts Center Museum in Chicago. Stroll along the lakeside or experience the fascinating museums 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
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.