Palmer Square Vacations from $548

Book a Hotel + Flight or Car together to unlock savings

Your Palmer Square Vacation

Book a Palmer Square vacation package and experience the way of life and rhythm of this vibrant neighborhood. With all your travel plans taken care of, the only thing you need to worry about here is having a good time. When it's time to see the sights, you'll find loads of big-name attractions nearby including Wrigley Field, DePaul University-Lincoln Park and Humboldt Park. Visit one, two or more during your trip to Palmer Square. Expedia is here to help put your plans into action. Book your dream Palmer Square vacation now.

The Latest Palmer Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$548
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Exceptionally clean

Reviewed on Sep 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$833
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$1,021
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$710
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Arlo Chicago

Arlo Chicago

Downtown Chicago
Save 100% on your flight
$658
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,326 reviews)
Everything was smooth and stress-free. The room was exactly what you need after a long travel day. The bed was comfortable and the bathroom was kept in perfect condition.

Reviewed on Sep 11, 2026

Where to stay in Palmer Square

Find the best Palmer Square areas and neighborhoods for the activities you enjoy most. Learn more about Palmer Square
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 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 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 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.

Palmer Square Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
$193 total
Sep 27 - Sep 28
Total with taxes and fees
8/10 Very Good! (10,205 reviews)
"My stay was great. But the hallway was off putting."

Reviewed on Sep 10, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$187 nightly
$223 total
Sep 21 - Sep 22
Total with taxes and fees
8/10 Very Good! (2,210 reviews)
"Property was clean in perfect location. Close to restaurants, shopping, and the beach"

Reviewed on Sep 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL
Kasa Magnificent Mile Chicago
See all 4,608 properties in Palmer Square
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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Flyover in Chicago

Flyover in Chicago

$28
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.