Pilsen Vacations

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    Save up to ￥109,000 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Room service - dining
    Jul 15 - Jul 20

    The Wade + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.4/10 - Very Good (1,846 reviews)
    "Todo bueno"
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥455,390
    ￥353,707
    per traveler
    found 16 hours ago
    The Wade
  • Terrace/patio
    Jul 15 - Jul 20

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,876 reviews)
    "The view from our room was awesome!!"
    Reviewed May 27, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥548,170
    ￥435,320
    per traveler
    found 16 hours ago
    Trump International Hotel & Tower Chicago
  • Exterior detail
    Jul 30 - Aug 5

    The Emily Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,319 reviews)
    "One of the worst hotel rooms I have stayed in. Tables and drawers made out of plywood, very uncomfortable beds, tv was mounted on side of bed so you had to turn to side to watch it. Low lights, makeup light mounted on opposite side of plug in so you had a cord in front of the mirror. Super basic and not worth the price. Location, bar and coffee were only positives. Would not stay here again."
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥565,609
    ￥456,772
    per traveler
    found 1 day ago
    The Emily Hotel
  • Dinner served
    Jul 15 - Jul 20

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Great hotel. Loved the lobby and our room. Would definitely stay here again."
    Reviewed May 19, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥444,254
    ￥365,090
    per traveler
    found 16 hours ago
    Kimpton Gray Hotel by IHG
  • Lobby
    Jul 15 - Jul 20

    The Langham, Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    "hands down one of the nicest hotels in the city - pool/gym/spa are all amazing. such a good 2nd floor lounge with great views. the staff is all so helpful, friendly"
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥566,982
    ￥473,233
    per traveler
    found 16 hours ago
    The Langham, Chicago

Where to stay in Pilsen

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

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

Pilsen Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ￥32,358 per night from Jun 3 to Jun 4
￥32,358
￥38,470 total
Jun 3 - Jun 4
includes taxes & fees
8/10 Very Good! (10,145 reviews)
"Very good location right in the heart of Downtown Chicago."

Reviewed on May 26, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is ￥38,064 per night from Jun 16 to Jun 17
￥38,064
￥49,794 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,263 reviews)
"The staff is very helpful, always ready to answer any question about the hotel or about the city of Chicago. The hotel is very clean , the breakfast is very good with many choices and the staff in the restaurant is excellent. My wife and I stayed in that place for eight days and seven nights and ..."

Reviewed on May 27, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ￥30,232 per night from Jun 16 to Jun 17
￥30,232
￥35,944 total
Jun 16 - Jun 17
includes taxes & fees
7.8/10 Good! (1,476 reviews)
"Everything"

Reviewed on May 27, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,705 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 , 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.

Discover the most popular places to visit in Pilsen

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(336 reviews)

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,904
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,276
per adult
92% of travellers recommend
Art Institute of Chicago
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.