Lower West Side Vacations from $237

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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.
Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
16.4/10 Exceptional! (999 reviews)
Rooms were clean and overall the hotel was nice

Reviewed on Nov 1, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,139, price is now $473 per person
$473
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.

Reviewed on Nov 17, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $522, price is now $242 per person
$242
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $509, price is now $251 per person
$251
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on Nov 18, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $482, price is now $254 per person
$254
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (1,001 reviews)
Everything was perfect

Reviewed on Nov 12, 2025

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
Downtown Chicago showing a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Lower West Side Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$87 nightly
The price is $102 total per night from Dec 8 to Dec 9
$102 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (5,268 reviews)
Rooms are clean. Personal great. Breakfast excellent. 💯 recommended 👌

Reviewed on Nov 17, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $149 total per night from Nov 25 to Nov 26
$149 total
Nov 25 - Nov 26
Total with taxes and fees
8.4/10 Very Good! (2,065 reviews)
Classy and classic! Never disappoints

Reviewed on Nov 16, 2025

Palmer House a Hilton Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,324 reviews)
Awesome location and valet was very helpful

Reviewed on Nov 18, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,794 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

Discover the most popular places to visit in Lower West Side

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.

Canalport Riverwalk Park

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.

Mexican Fine Arts Center Museum

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 fascinating museums.

American Police Center & Museum

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% 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.