Palmer Square Holidays from AU$3,718

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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.

Top Holiday Package Deals in Palmer Square

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

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Price was AU$4,210, price is now AU$3,718 per person
AU$3,718
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
8/10 Very Good! (9,398 reviews)
Old rundown hotel that needs to be upgraded. I stayed here to attend an event at The Auditorium. This is a large complex that includes shopping and other amenities that is near many tourist locations.

Reviewed on 24 Oct 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$5,267, price is now AU$4,373 per person
AU$4,373
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
This hotel was nearly perfect! Great staff. Great location. Clean. My only complaint was the ice machine was broken on our floor. We reported it to staff 3 separate occasions and it wasn’t fixed in the 5 days we were there. Hotel is located on a busy street so there is some noise but if that Doesn't bother you… this is perfect. Very walkable location! The staff there are fantastic. From the moment you walk in until the moment you leave. They understand the assignment. Highly recommend.

Reviewed on 21 Oct 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$4,694, price is now AU$3,955 per person
AU$3,955
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on 20 Oct 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was AU$4,512, price is now AU$3,955 per person
AU$3,955
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Everything was amazing. I will definitely be back!

Reviewed on 23 Oct 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$4,597, price is now AU$4,062 per person
AU$4,062
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We had an amazing time staying at the Arlo. The staff was very friendly, the check-in/check-out process was very fast. The room was always clean. The location of the hotel is extremely convenient. Everything was awesome. I’m 100% coming back when I’m in Chicago again.

Reviewed on 22 Oct 2025

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
Downtown Chicago featuring 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

Our pick of the best Palmer Square 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
The price is AU$306 per night from 2 Nov to 3 Nov
AU$306
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,498 reviews)
The website for the gazebo restaurant within the hotel said there was an extensive menu. When you get down to the place it’s a small buffett set up which was similar to any other continental breakfast with some cereal, muffins, fruit, some biscuits, bacon and sausage etc. There was also a man at ...

Reviewed on 20 Oct 2025

Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is AU$216 per night from 25 Nov to 26 Nov
AU$216
25 Nov - 26 Nov
includes taxes & fees
8.8/10 Excellent! (1,943 reviews)
Great location if you have meetings at the Mart which you can reach through escalator and a bridge that takes you directly to the second floor. The hotel is well run Good breakfast and friendly staff. Rooms are clean but they should start “refreshing” some of the features like carpets which seem ...

Reviewed on 13 Oct 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
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
The price is AU$202 per night from 16 Nov to 17 Nov
AU$202
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,133 reviews)
Every think was wonderful except the heater wasn’t working and the toilet was loose.

Reviewed on 19 Oct 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,706 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.
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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 AU$3,718. 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.

Discover the most popular places to visit in Palmer Square

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Activities

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.