Pilsen Vacation Packages

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Top Holiday Package Deals in Pilsen

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.

Reviewed on Aug. 4, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 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
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on Aug. 3, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (3,055 reviews)
Amazing hotel!! The rooms were spacious and its right in a prime area to explore all of chicago

Reviewed on Aug. 3, 2025

Where to stay in Pilsen

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

Pilsen 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 CA $185 per night from Aug 6 to Aug 7
CA $185
CA $217 total
Aug 6 - Aug 7
includes taxes & fees
7.8/10 Good! (8,940 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug. 1, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 21 to Aug 22
CA $239
CA $315 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,825 reviews)
"The iconic and historic hotel are a magnificent landmark and there’s a thrill to entering the lobby every time!"

Reviewed on Aug. 4, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,335 reviews)
"Thanks beautiful place"

Reviewed on Aug. 3, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,740 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Pilsen vacation package cost?
Our Pilsen packages, which begin at just CA $1,189, 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 featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

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

Michigan Avenue

4.5/5(19 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
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.