Pilsen Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Pilsen, Chicago, Illinois, USA

Lux Apts with Lake Views and Top Amenities
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10.0 (4 Reviews)
13 Bedrooms 32 Guests
The Publishing House B&B
From£205 per night
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9.8 (206 Reviews)
1 Bedroom 2 Guests
Villa Dubois Guest House
From£143 per night
8.6 (89 Reviews)
1 Bedroom 2 Guests
Freshly Minted 2BR - Elegance & Comfort in Central Chicago
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10.0 (4 Reviews)
2 Bedrooms 6 Guests
Mccormick Place Guest House
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7.8 (60 Reviews)
1 Bedroom 2 Guests
Bright & Spacious Boho Oasis: A Warm Retreat
New
1 Bedroom 3 Guests
Cozy Chic Retreat Near Downtown - Sleeps 7
New
2 Bedrooms 7 Guests
The Orleans Floor 3 Private rooftop deck
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10.0 (2 Reviews)
4 Bedrooms 16 Guests
Large 4BR Cozy Stay Near Field Museum & McCormick
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10.0 (2 Reviews)
4 Bedrooms 10 Guests
1 Free Parking Gym Balcony Sleeps 10
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10.0 (2 Reviews)
3 Bedrooms 10 Guests
24th Floor 2BR Luxury Skyline Grant Park
New
2 Bedrooms 8 Guests
Gym Garage Parking Balcony Sleeps 4
10.0 (2 Reviews)
1 Bedroom 4 Guests
South Loop 2BR Chicago 420-Friendly Near McCormick & Chinatown
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10.0 (1 Review)
2 Bedrooms 6 Guests
Luxury 2BD-2BA View-Gym-Rooftop
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10.0 (1 Review)
2 Bedrooms 4 Guests
Two-Story Penthouse, City Views, Pool, Gym
10.0 (11 Reviews)
2 Bedrooms 8 Guests
LIVN West Loop Chicago King Studio
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10.0 (1 Review)
4 Bedrooms 2 Guests
Stylish Apartment near Chicago Downtown
10.0 (4 Reviews)
1 Bedroom 2 Guests
Dtown Penthouse 11+Parking, Gym, Pvt Patio
10.0 (11 Reviews)
2 Bedrooms 7 Guests
Cabin 105 by 747 Lofts
From£151 per night
10.0 (1 Review)
1 Bedroom 2 Guests
The Landmark; a comfy suite near McCormick Place
10.0 (10 Reviews)
1 Bedroom 2 Guests
The Langham, Chicago
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9.8 (1004 Reviews)
1 Bedroom 2 Guests
Cabin 104 by 747 Lofts
From£206 per night
10.0 (9 Reviews)
1 Bedroom 2 Guests
LIVN West Loop Chicago 2 BR City View
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10.0 (1 Review)
6 Bedrooms 4 Guests
Chic River North 2BD Condo with Parking & Balcony
10.0 (6 Reviews)
2 Bedrooms 4 Guests
3BR Luxury Modern Apartment
From£340 per night
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10.0 (1 Review)
3 Bedrooms 8 Guests
Cabin 302 by 747 Lofts
From£223 per night
10.0 (6 Reviews)
1 Bedroom 3 Guests
Stylish 3BR Gem in Prime Location
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10.0 (1 Review)
1 Bedroom 8 Guests
River North 2BD Condo: Parking, Balcony, Laundry
10.0 (5 Reviews)
2 Bedrooms 5 Guests
Downtown 2bd #4 - Near Grant Park, Museums, Lake
10.0 (5 Reviews)
2 Bedrooms 5 Guests
River North 2BD 2BA Retreat with Balcony & Parking
10.0 (5 Reviews)
2 Bedrooms 5 Guests
LIVN West Loop Chicago 1 BR
From£271 per night
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10.0 (1 Review)
1 Bedroom 2 Guests
LIVN West Loop Chicago Queen Superior Studio
10.0 (5 Reviews)
1 Bedroom 2 Guests
Charming 2-bedroom apartment in hip Chicago
10.0 (5 Reviews)
2 Bedrooms 4 Guests
Modern 3BR Near McCormick & South Loop
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10.0 (1 Review)
1 Bedroom 8 Guests
Luxury Penthouse Loft w/Terrace 507 | River North
10.0 (4 Reviews)
2 Bedrooms 8 Guests
Modern River West 2BR with W&D by Zencity
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10.0 (1 Review)
2 Bedrooms 3 Guests

About Pilsen Vacation Rentals

With more than 3488 Pilsen vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Pilsen.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Pilsen, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Pilsen. Places to stay near Pilsen are 753.53 ft² on average, with prices averaging £329 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Pilsen with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Other Places to Stay in Pilsen, IL


Frequently Asked Questions About Pilsen?

What are the top vacation rentals in Pilsen?

How many Rentbyowner vacation rentals are available in Pilsen?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 3488 in the Pilsen area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pilsen. 

Nearby Neighborhood (4)

NeighborhoodProperty Count
Near West Side Vacation Rentals in Chicago, Illinois 246
University Village / Little Italy Vacation Rentals in Chicago, Illinois 65
Lower West Side Vacation Rentals in Chicago, Illinois 56
Heart of Chicago Vacation Rentals in Chicago, Illinois 39