Lower West Side Vacation Packages 2026 from $463

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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.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

$463

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,779 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$507

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

$584

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Very clean room, great friendly staff.

Reviewed on Aug 15, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$716

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$508

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Hotel amenities were great, and the suite was nice enough. The mattress was a little springy, but not terrible. I was frustrated by finding out about an amenities fee at the end that added roughly $100 to my cost at the hotel. That felt a lot like the “hidden fee” that so many booking services seek to advertise not having. That hotel would probably say that they don’t hide that fee, that it’s stated in the hotel stay conditions or something to that affect; but I’d argue that most people staying there for the first time are probably unaware of the fee prior to coming. If they want to charge an additional amount for the amenities at the hotel (which I admit are great), put the cost for the amenities into the price per night for the room itself. If you advertise the amenities at the hotel as a perk of staying there, consider that part of the upfront price rather than something that’s informed to you as you check out.

Reviewed on Aug 14, 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! (10,197 reviews)

"Do not come here if you have a baby"

Reviewed on Aug 15, 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! (1,997 reviews)

"The gym"

Reviewed on Aug 15, 2026

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$246 nightly

$288 total

Sep 5 - Sep 6

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.

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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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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.

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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.

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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 fascinating museums in this vibrant area.

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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.

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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 entertainment choices in this vibrant area.

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 $463

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

Eurostars Magnificent Mile

Swissotel - Chicago

Hotel Riu Plaza Chicago

Level Chicago Fulton Market

Level Chicago – Old Town

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

Mexican Fine Arts Center Museum

Things to do

360 CHICAGO Observation Deck

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Navy Pier Centennial Wheel Ticket