Pilsen Vacation Packages 2026 from $407

Pilsen flight + hotel vacation packages

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

Pendry Chicago

Downtown Chicago

$407

per person

Mar 13 - Mar 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$630

per person

Mar 14 - Mar 18

found 9 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$466

per person

Mar 13 - Mar 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

$553

per person

Mar 12 - Mar 16

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$448

per person

Mar 13 - Mar 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Pilsen hotels deals

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$174 total

Dec 28 - Dec 29

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$149 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A library, express check-in, and express check-out are also on offer.

Free WiFi

Air conditioning

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$103 total

Dec 29 - Dec 30

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$163 total

Dec 28 - Dec 29

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

Eurostars Magnificent Mile

660 North State Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$110 total

Jan 22 - Jan 23, 2026

Total with taxes and fees

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Spa

Free WiFi

Don't see what you're looking for?

See all available properties in Pilsen

View all properties

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.

Popular places to visit

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.

Wrigley Field

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

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Frequently asked questions

How much are vacation packages to Pilsen?

Vacation packages, including flights and hotels in Pilsen, start from as low as $407. Turn your daydreams into reality and book your dream trip with Travelocity today.

Where can I get the best vacation package deals for Pilsen?

Head straight to Travelocity. With access to 400 airline partners and an incredible 1,000,000 hotels around the world, creating the perfect Pilsen package deal couldn't be simpler.

Why should I book my Pilsen vacation package with Travelocity?

The three S's — savings, support and a stress-free booking — are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.

Can I save money on my Pilsen car rental if I book it with my hotel or flight?

Booking a Pilsen vacation package with Travelocity is an easy way to save your time and money. Choose a hotel, flight and car, or any combination of them, and score great discounts. It's also possible to add in some experiences. Once you've collected the keys to your rental car, venture out of the neighborhood and see what the area has to offer. Approximately 40 mi from Pilsen, Six Flags Great America is the ideal road trip.