Lower West Side Vacation Packages
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Top Holiday Package Deals in Lower West Side
Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.
Reviewed on Jul. 15, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on Jul. 16, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
This hotel is designed well and has a great little bar downstairs along with a nice restaurant/cafe adjacent to the property. The front desk girls are mostly helpful specifically Muriel who made my stay extremely comfortable and gave me tons of recs on eats, etc. I was so thankful to have her around!
I had AC issues with a crazy rattling noise in my first room and was upgraded to another nicer room my last night there. Neither of the beds were very comfortable - I think adding a pillow top would be helpful! The rooms are cute though!
Reviewed on Jul. 14, 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
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.
Lower West Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Aug 5 to Aug 6
CA $203
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,979 reviews)
"The hotel is an old property, but the bedrooms were nicely renovated. The location is the highlight... nice views, close to everything, walkable distance to downtown and the lake."
Reviewed on Jul. 15, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $301 per night from Aug 7 to Aug 8
CA $301
CA $397 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (2,031 reviews)
"Great location ! Small but nice room ."
Reviewed on Jul. 13, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Aug 10 to Aug 11
CA $201
CA $236 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,444 reviews)
"clean...close to attractions.."
Reviewed on Jul. 14, 2025
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.
Frequently asked questions
Things to do
Wendella's 90-min Chicago River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
CA $62
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.