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
FromGB £154 per night
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9.8 (195 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
FromGB £68 per night
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8.8 (46 Reviews)
1 Bedroom 2 Guests
Villa Dubois Guest House
FromGB £66 per night
8.6 (80 Reviews)
1 Bedroom 2 Guests
1 Free Parking Gym Balcony Sleeps 12
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10.0 (2 Reviews)
1 Bedroom 10 Guests
Hamaline Luxury Guest House
FromGB £216 per night
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10.0 (2 Reviews)
3 Bedrooms 6 Guests
52nd Floor MagMile Penthouse Views Fireplace Pool
10.0 (408 Reviews)
1 Bedroom 4 Guests
The Orleans Floor 3 Private rooftop deck
10.0 (2 Reviews)
4 Bedrooms 16 Guests
53 Floor MagMile Penthouse Views, Balcony, Pool
10.0 (244 Reviews)
2 Bedrooms 6 Guests
West Loop - City Views With In & Out Parking 5
10.0 (2 Reviews)
1 Bedroom 10 Guests
51st Floor MagMile Penthouse Views Balcony Pool
10.0 (227 Reviews)
1 Bedroom 4 Guests
Large 4BR Cozy Stay Near Field Museum & McCormick
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10.0 (1 Review)
4 Bedrooms 10 Guests
2-Story Penthouse Views, Fireplace, Pool, Gym
10.0 (212 Reviews)
2 Bedrooms 8 Guests
52nd Floor Penthouse with Skyline Views & Pool
10.0 (64 Reviews)
1 Bedroom 4 Guests
McCormick 3BR HUGE unit, Optional Parking with Ping-pong
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10.0 (1 Review)
3 Bedrooms 8 Guests
50th Floor Mag Mile Views, Balcony, Pool, Gym
10.0 (33 Reviews)
1 Bedroom 2 Guests
Spacious & private! Free parking! Great location!
10.0 (31 Reviews)
1 Bedroom 2 Guests
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
10.0 (26 Reviews)
2 Bedrooms 6 Guests
Trendy West Town Flat - 2 bed/1.5 bath with parking
10.0 (25 Reviews)
2 Bedrooms 5 Guests
Flexhome West Town 2BR Duplex Apt T2
FromGB £570 per night
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10.0 (1 Review)
2 Bedrooms 6 Guests
Family Friendly 2-Bedroom w/Kitchen & Laundry
10.0 (20 Reviews)
2 Bedrooms 5 Guests
Luxury 2BD-2BA View-Gym-Rooftop
FromGB £440 per night
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10.0 (1 Review)
2 Bedrooms 4 Guests
Spacious loft in the heart of West Town, Noble Square Chicago
10.0 (13 Reviews)
1 Bedroom 4 Guests
Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
10.0 (11 Reviews)
1 Bedroom 7 Guests
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
10.0 (11 Reviews)
2 Bedrooms 4 Guests
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
10.0 (2 Reviews)
1 Bedroom 5 Guests
Gilean Urban Retreat
FromGB £422 per night
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10.0 (1 Review)
3 Bedrooms 6 Guests
Art Villa
FromGB £768 per night
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10.0 (2 Reviews)
1 Bedroom 2 Guests
Sun-Drenched 1BR Apartment
FromGB £131 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
Cabin 105 by 747 Lofts
FromGB £102 per night
10.0 (1 Review)
1 Bedroom 2 Guests
The Langham, Chicago
FromGB £381 per night
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9.8 (1002 Reviews)
1 Bedroom 2 Guests
3BR Luxury Modern Apartment
FromGB £339 per night
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10.0 (1 Review)
3 Bedrooms 8 Guests
Stylish 3BR Gem in Prime Location
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10.0 (1 Review)
1 Bedroom 8 Guests
Modern 3BR Near McCormick & South Loop
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10.0 (1 Review)
1 Bedroom 8 Guests
Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
10.0 (1 Review)
2 Bedrooms 4 Guests
Modern River West 2BR with W&D by Zencity
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10.0 (1 Review)
2 Bedrooms 3 Guests
3 Bed 2 Bath Chicago Retreat w Balcony & Parking
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10.0 (1 Review)
3 Bedrooms 6 Guests
Downtown 2bd #5 +Gym near Park, Lake, Museums
10.0 (1 Review)
2 Bedrooms 5 Guests
New Luxury 3 Bdr Apt in Chicago C9
10.0 (1 Review)
3 Bedrooms 6 Guests
Arcade Free Parking TYLER the creator inspired
10.0 (1 Review)
1 Bedroom 8 Guests
Stylish 2BR Retreat in the Heart of Chicago
10.0 (1 Review)
2 Bedrooms 4 Guests

About Pilsen Vacation Rentals

With more than 3319 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 723.33 ft² on average, with prices averaging GB £286 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 3319 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 371
University Village / Little Italy Vacation Rentals in Chicago, Illinois 106
Lower West Side Vacation Rentals in Chicago, Illinois 55
Heart of Chicago Vacation Rentals in Chicago, Illinois 38