Lower West Side Vacation Packages 2026 from $481

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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 Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$481

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (149 reviews)

Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in. 4 days later, the on-line booking co. Said the manager did not agree to release my reservation. Unethical procedurers.

Reviewed on Aug 12, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$746

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

N/a

Reviewed on Aug 18, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$737

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$515

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,899 reviews)

Great location and pleasant staff.

Reviewed on Aug 17, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$610

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Overall, this is a great hotel. My family loved the rooms and the fitness center. The staff were mostly great too. We will definitely stay here again if we come back to Chicago. We were given rooms that were 28 floors apart despite making our reservation months in advance. Yes, it was one reservation which included 2 rooms. Both the shower and toilet space was fairly tight. Other than that, we are very happy.

Reviewed on Aug 18, 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.

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.

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.

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.

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.

Lower West Side Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$109 nightly

$130 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,247 reviews)

"Hotel needs to be renovated.. it’s in really rough shape. ..actual spider webs on the windows.. smells bad.. it’s wild.."

Reviewed on Aug 17, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Aug 30 - Aug 31

Total with taxes and fees

8/10 Very Good! (2,029 reviews)

"Very friendly and professional staff. Building does show its age though."

Reviewed on Aug 18, 2026

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$241 nightly

$282 total

Sep 12 - Sep 13

Total with taxes and fees

See all 4,611 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.

Stay near popular Lower West Side attractions

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.

See properties

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.

See properties

Chicago Arts District

You can spend time exploring the galleries in Chicago Arts District in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

See properties

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 acclaimed art scene and entertainment choices in this vibrant area.

See properties

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.

See properties

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 fascinating museums in this vibrant area.

See properties

Cooper Dual Language Academy

You can spend time browsing the exhibits at Cooper Dual Language Academy in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

See properties

American Police Center & Museum

You can spend time exploring the galleries in American Police Center & Museum in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

See properties

Things to do

360 CHICAGO Observation Deck

$27

per adult

86% of travellers recommend

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47

per adult

88% of travellers recommend

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25

per adult

90% of travellers recommend

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.

Lower West Side Vacations from $481

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Lower West Side Vacation

The Latest Lower West Side Vacation Packages

The Talbott, Autograph Collection

Hotel Riu Plaza Chicago

Level Chicago Fulton Market

Hotel Felix River North/Magnificent Mile

Swissotel - Chicago

Where to stay in Lower West Side

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Lower West Side Hotel Deals

Congress Plaza Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago O'Hare Airport

Stay near popular Lower West Side attractions

Canalport Riverwalk Park

Radius - Chicago

Chicago Arts District

National Museum of Mexican Art

The Geraghty

St Pius Church

Cooper Dual Language Academy

American Police Center & Museum

Things to do

360 CHICAGO Observation Deck

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Navy Pier Centennial Wheel Ticket