Pilsen Vacations from ¥284,169

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The Latest Pilsen Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥284,169
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Great Accommodations for a quick weekend. The gym was topnotch.

Reviewed on Aug 25, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥407,670
per person
Oct 5 - Oct 10
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,828 reviews)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Downtown Chicago
¥377,232
per person
Oct 5 - Oct 10
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,398 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥489,023
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥390,098
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.2/10 Wonderful! (1,055 reviews)
The water pressure in our room was hopeless but everything else about our room and the property was perfect. The amenities (gym, pool, etc) were amazing and our room was a great size and had a very comfortable bed

Reviewed on Aug 25, 2026

Where to stay in Pilsen

Find the best Pilsen areas and neighborhoods for the activities you enjoy most. Learn more about Pilsen
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.

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 neon sign reading "Blue Chicago on Clark" in an ornate archway.

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 city street with a train passing overhead, cars, pedestrians, and a red brick building.

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 wooden pavilion with a view of a city skyline and a body of water.

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.

Pilsen Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
¥16,962
¥20,168 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (10,314 reviews)
"Great location, serious service and sanitation failures. Rooms are dated, which could be charming. The TV has basic channels only, so bring a Chromecast or Roku. The in room tablet is useless; that money should have gone to the TVs. Room service never came. I ordered biscuits and gravy and pancakes. ..."

Reviewed on Aug 25, 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
¥21,313
¥25,340 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (2,096 reviews)
"The international breakfast was amazing. The valet was prompt."

Reviewed on Aug 25, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
¥40,644
¥47,713 total
Sep 18 - Sep 19
includes taxes & fees
8.4/10 Very Good! (2,442 reviews)
"It is located walking distance within the airport"

Reviewed on Aug 25, 2026

Hilton Chicago O'Hare Airport
See all 4,548 properties in Pilsen
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 Pilsen vacation package cost?
Our Pilsen packages, which begin at just ¥284,169, are an awesome way to save big bucks. Pick and choose your preferred flights, hotels and rental cars to create a custom-built getaway.
How do I get a cheap travel package to Pilsen?
Bundle your flights and hotels with Expedia to save big on your next exciting adventure. With over 550 air carriers and 1,000,000 hotel options across the world, your Pilsen vacation package can be customized exactly to suit your budget. With all that extra money, why not add some awesome tours and activities? It's an easy way to unlock even more savings. Your dream getaway to Pilsen is closer than you thought!
Where should I stay in Pilsen?
Urban adventurers come from all corners of the globe to experience University of Illinois Chicago and United Center in Pilsen. Book a room within walking distance of these awesome attractions and visit them whenever you please.
How far in advance should I book my Pilsen vacation?
While not all air carriers advertise tickets early, you can usually compare international flights on Expedia up to a year in advance. This is the time when you'll nab some fantastic bargains. If you're booking late, you may still be in luck. Sometimes the cheapest prices become available a few weeks before departure.
What does an Expedia Pilsen travel package include?
Packages include flights, hotels and rental cars, but you can combine any of them to create your dream Pilsen escape. You can also add on fun things like activities and experiences once you've made your booking. You're the boss! When you combine your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Pilsen travel package?
Our prices are always low. However, you'll pick up an even better deal when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and a huge range of choice.
Can I choose my airline with a Pilsen Expedia vacation package?
The choice is all yours! We offer more than 550 airlines all over the world, so you can customize your Pilsen adventure according to your budget and style.
If I'm not able to travel, can I cancel my Pilsen vacation package?
Plans can change in a flash, so yes, you can. You may be able to cancel or alter your Pilsen vacation package for free within 24 hours of booking. For older bookings, you can still make the necessary changes, but your car rental company, airline or hotel may charge a fee. Looking for more information? Visit our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Stay near popular Pilsen attractions

St Pius Church

After visiting St Pius Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
See properties

Simone's

Simone's is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the area's art scene and festivals.
See properties

Chicago Art Department

After visiting Chicago Art Department, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge 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.