Lower West Side Vacations from $133

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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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $268, price is now $133 per person
$133
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $310, price is now $159 per person
$159
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I thoroughly enjoyed my time at Pendry Chicago. I stayed in a tower king room. I originally was going to stay in a suite but the normal king room was very spacious for one person. The valet service was pretty quick and the valets were all very nice. The front desk clerk was extremely helpful and professional. I loved staying right on Michigan Ave and within walking distance to so many things. I read some reviews saying safety was a concern but I didn’t experience any safety issues. They lock the doors on Michigan Ave after a certain point to keep the flow of traffic thru a better monitored entrance. I also took an evening(beginning around 9:30pm) stroll around Millennium Park, down to Buckingham fountain and back up Michigan Ave to the river and the surroundings blocks around the hotel. At no point did I feel unsafe and would highly recommend this hotel to anyone coming to Chicago. The location is fantastic, the employees are amazing and the rooms are comfy. What more could you ask for?

Reviewed on Nov 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $836, price is now $438 per person
$438
per person
Feb 12 - Feb 15
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $558, price is now $306 per person
$306
per person
Feb 12 - Feb 15
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.

Reviewed on Nov 25, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was $409, price is now $229 per person
$229
per person
Feb 7 - Feb 11
found 20 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
Clean rooms, great location in Evanston near the university. Helpful staff.

Reviewed on Nov 17, 2025

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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

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
$136 nightly
The price is $155 total per night from Dec 21 to Dec 22
$155 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,097 reviews)
Enjoyed relaxing in the lobby

Reviewed on Nov 26, 2025

Palmer House a Hilton Hotel
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 21 to Dec 22
$102 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (5,291 reviews)
All above.

Reviewed on Nov 24, 2025

Embassy Suites by Hilton Chicago Downtown River North
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! (3,382 reviews)
Great location and very convenient.

Reviewed on Nov 26, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,845 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

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

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

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% 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
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.