Lower West Side Vacations from $519

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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.
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Save 100% on your flight
Price was $766, price is now $519 per person
$519
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (1,023 reviews)
Not a traditional hotel but there was someone at the front desk to help with the check in process. Great location no complaints

Reviewed on Jun 19, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,222, price is now $790 per person
$790
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,665, price is now $1,111 per person
$1,111
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Usually this is one of the best property but this time they had water pipe burst and elevators werent working because of that. It was very inconvinient for this stay.

Reviewed on Jun 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,101, price is now $738 per person
$738
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
Great hotel, would definitely stay here again!

Reviewed on Jun 21, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,371, price is now $932 per person
$932
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 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
Downtown Chicago

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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,148 reviews)
"No hot water. Room was outdated"

Reviewed on Jun 21, 2026

Congress Plaza 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
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (4,452 reviews)
"Clean room exelent"

Reviewed on Jun 19, 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
$131 nightly
The price is $155 total per night from Jun 30 to Jul 1
$155 total
Jun 30 - Jul 1
Total with taxes and fees
7.8/10 Good! (1,601 reviews)
"Our stay was amazing! Staff was very helpful!"

Reviewed on Jun 19, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,709 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 acclaimed theater scene 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 acclaimed theater scene.

American Police Center & Museum

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$154
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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.