Palmer Square Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Palmer Square Holiday

Book a Palmer Square holiday package and experience the way of life and rhythm of this vibrant neighbourhood. 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 holiday now.

Our guide on 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.

Find hotels in Downtown Chicago
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile
A river with yellow boats, a bridge, and tall buildings.

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

Find hotels in The Loop
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

Our pick of the best Palmer Square Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$265
7 Oct - 8 Oct
includes taxes & fees
8/10 Very good! (10,205 reviews)
"My stay was great. But the hallway was off putting."

Reviewed on 10 Sept 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
AU$297
12 Oct - 13 Oct
includes taxes & fees
8/10 Very good! (2,210 reviews)
"Property was clean in perfect location. Close to restaurants, shopping, and the beach"

Reviewed on 11 Sept 2026

The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL
Get rates
Kasa Magnificent Mile Chicago
See all 4,612 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays
family friendly holidays
Family Friendly Holidays
Family Friendly Holidays
golf holidays
Golf Holidays
Golf Holidays
luxury holidays
Luxury Holidays
Luxury Holidays
romantic holidays
Romantic Holidays
Romantic Holidays
ski holidays
Ski Holidays
Ski Holidays
honeymoon holidays
Honeymoon Holidays
Honeymoon Holidays
pet friendly holidays
Pet-friendly Holidays
Pet-friendly Holidays
Spa Holidays
Spa Holidays
Spa Holidays

Frequently asked questions

How much does a Palmer Square holiday package cost?
Say yes to new adventures with our Palmer Square holiday packages, which start from just . Choose the flights and hotels that suit your plans. Then, add on a couple of tours or activities for an unforgettable getaway.
How do I get a cheap travel package to Palmer Square?
Booking a Palmer Square holiday package with Expedia is one of the easiest ways to save. We offer access to over 550 partner airlines and 1 000 000 hotels spread across the globe. With such a huge range to select from, you'll have no issues pulling together your perfect trip.
Where should I stay in Palmer Square?
Take the hassle out of sightseeing by staying someplace just a stone's throw away from Palmer Square's biggest attractions. Wrigley Field and Lincoln Park Zoo are two visitor favourites.
How far in advance should I book my Palmer Square holiday?
To score cheap prices, book nice and early. Airlines usually release flights, along with some of the lowest fares, nearly a year in advance. Hotels, activities and car rental should also be booked early so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Palmer Square, there are always lots of great deals to be had on Expedia. Book something in today!
What does an Expedia Palmer Square travel package include?
Expedia has everything you need to book your Palmer Square getaway, but what your package looks like is your call. Choose from a combination of rental cars, hotels and flights. Looking for some activities to keep you busy? Once you've made your booking, you can add them too. No matter your style, there's a holiday package to meet your needs.
What should I know before booking a Palmer Square travel package?
You'll pick up great savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything in one place will make your trip planning easier. So why waste your money or time? Whether you're putting together a ritzy city getaway or a budget solo adventure, check out our holiday packages today.
Can I choose my airline with a Palmer Square Expedia holiday package?
Yes, the choice is yours. We offer more than 550 airlines worldwide, so you can design your Palmer Square adventure according to your travel preferences.
If I'm not able to travel, can I cancel my Palmer Square holiday package?
Yes, it's possible to cancel your Palmer Square booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$36
per child
100% of travellers recommend
Chicago Sightseeing River and Lake 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.