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Palmer Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

The Latest Palmer Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with a view of a cityscape through a large window, a floor lamp, a sofa with cushions, and a small table with a plant.
    Jan 7 - Jan 11

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    4 nights
    3.5 star property
    9.0/10 - Wonderful (1,552 reviews)
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $913
    CA $728
    per traveller
    found 1 day ago
    Sports Illustrated Resorts Chicago
  • A cityscape with modern high-rise buildings, a river, and a bridge.
    Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,878 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,322
    CA $979
    per traveller
    found 18 hours ago
    Sheraton Grand Chicago Riverwalk
  • A modern hotel with a curved glass facade, a prominent 'SOFITEL' sign, and a colorful entrance area.
    Jan 21 - Jan 24

    Sofitel Chicago Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (2,678 reviews)
    Roundtrip • Calgary (YYC) - Chicago (ORD)
    YYC - ORD • Nonstop ORD - YYC • 1 stop
    CA $1,490
    CA $1,174
    per traveller
    found 1 hour ago
    Sofitel Chicago Magnificent Mile
  • A hotel entrance with a marquee sign, outdoor seating, and a well-lit facade.
    Jan 21 - Jan 24

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (194 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,195
    CA $943
    per traveller
    found 18 hours ago
    The Talbott, Autograph Collection
  • Interior entrance
    Dec 28 - Jan 2

    Chicago Lake Shore Hotel + Flight

    Kenwood
    5 nights
    3.0 star property
    7.0/10 - Good (1,013 reviews)
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,409
    CA $1,116
    per traveller
    found 1 day ago
    Chicago Lake Shore Hotel

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
Learn more about Palmer Square
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

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 large, historic building with a central tower and multiple windows, located near a body of water.

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 river with a city skyline in the background, surrounded by green trees and grass.

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.

What to do near Palmer Square

360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
See all activities near Palmer Square

Palmer Square Hotel Deals

The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
6 km from Palmer Square
9.0 out of 10, Wonderful, (1,434 reviews)
The price is CA $125
CA $190 total
includes taxes & fees
Nov 22 - Nov 23
Claridge House Chicago, Tapestry Collection by Hilton
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.
See all properties in Palmer Square

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 $728. 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.

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