Palmer Square Vacations from ￥313,970

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The Latest Palmer Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was ￥384,375, price is now ￥313,970 per person
￥313,970
per person
Oct 5 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,653 reviews)
The views were spectacular

Reviewed on Sep 4, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥534,950, price is now ￥388,212 per person
￥388,212
per person
Oct 5 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service

Reviewed on Sep 4, 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥500,885, price is now ￥391,596 per person
￥391,596
per person
Oct 5 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
It was great for a short stay with my family. We enjoyed the location and proximity to public transportation.

Reviewed on Sep 4, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was ￥444,359, price is now ￥357,198 per person
￥357,198
per person
Oct 5 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great modern location. The fee onsite was different that the fee told but it was a great stay. I would stay here again.

Reviewed on Sep 1, 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 ￥440,848, price is now ￥357,674 per person
￥357,674
per person
Oct 5 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,129 reviews)
The Lake was beautiful.

Reviewed on Sep 5, 2025

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 showing 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

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 ￥21,886 per night from Sep 22 to Sep 23
￥21,886
￥25,692 total
Sep 22 - Sep 23
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥26,301 per night from Sep 14 to Sep 15
￥26,301
￥30,876 total
Sep 14 - Sep 15
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥24,724 per night from Sep 22 to Sep 23
￥24,724
￥29,024 total
Sep 22 - Sep 23
includes taxes & fees
The Wade
See all 4,669 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.

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 ￥313,970. 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.

Discover the most popular places to visit in Palmer Square

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

￥6,127
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥5,986
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,651
per adult
96% of travellers recommend
Chicago By Night River & 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.