Palmer Square Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in Palmer Square
Price found within the past 48 hours. Click for updated prices.
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
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.
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.
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.
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.
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
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $252
CA $300 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (5,466 reviews)
"I had a fantastic stay! The location was perfect—right next to the Hello Kitty Café and directly across from the Trump Hotel, which made for a beautiful view from my room. Everything was clean, comfortable, and overall a great experience. The only downside was that only one elevator was operating ..."
Reviewed on Sep 22, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $259
CA $308 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very good! (10,192 reviews)
"I’ve stayed here for years. Every riot"
Reviewed on Sep 22, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $264
CA $314 total
Sep 30 - Oct 1
includes taxes & fees
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
How much does a Palmer Square vacation package cost?
Say yes to new adventures with our Palmer Square vacation packages, which start from just CA $772. 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 vacation 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 favorites.
How far in advance should I book my Palmer Square vacation?
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 vacation 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 vacation packages today.
Can I choose my airline with a Palmer Square Expedia vacation 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 vacation 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.