Pilsen Vacation Rentals

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

The Publishing House B&B
FromR4,932 per night
|
9.8 (208 Reviews)
1 Bedroom 2 Guests
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
10.0 (35 Reviews)
3 Bedrooms 10 Guests
LIVN Millennium Park Downtown Chicago Prem Studio
|
10.0 (4 Reviews)
3 Bedrooms 2 Guests
Villa Dubois Guest House
FromR2,911 per night
8.2 (104 Reviews)
1 Bedroom 2 Guests
Top Floor Views + Central Comfort
10.0 (9 Reviews)
2 Bedrooms 6 Guests
Mccormick Place Guest House
|
7.4 (66 Reviews)
1 Bedroom 2 Guests
Historic Charm + Modern Comfort for Tourists
10.0 (8 Reviews)
2 Bedrooms 5 Guests
The Orleans Floor 3 Private rooftop deck
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10.0 (2 Reviews)
4 Bedrooms 16 Guests
Luxury Penthouse: Iconic Views + Exclusive Comfort
10.0 (7 Reviews)
4 Bedrooms 9 Guests
Exclusive 3BR with Views, Ideal for Tourists
10.0 (6 Reviews)
3 Bedrooms 6 Guests
1 Free Parking Gym Balcony Sleeps 10
|
10.0 (2 Reviews)
3 Bedrooms 10 Guests
High-End 3BR Retreat + Steps to Millennium Park
10.0 (5 Reviews)
3 Bedrooms 6 Guests
LIVN West Loop Chicago 1 BR
FromR7,045 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
Luxury 2BR near Millennium Park + 5-Star Reviews
10.0 (5 Reviews)
2 Bedrooms 5 Guests
Luxury Fulton Market Condo - Prime Location
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
West Loop 2BR with Skyline Views + Prime Location
10.0 (5 Reviews)
2 Bedrooms 6 Guests
Penthouse Escape + Vibrant West Loop Access
10.0 (4 Reviews)
3 Bedrooms 7 Guests
Gym Garage Parking Balcony Sleeps 4
10.0 (2 Reviews)
2 Bedrooms 4 Guests
Spacious Penthouse Trio + Skyline Views for Groups
10.0 (3 Reviews)
9 Bedrooms 22 Guests
West Loop - City Views With In & Out Parking 4
10.0 (2 Reviews)
4 Bedrooms 10 Guests
Dual Penthouse Retreat: Perfect for Groups
10.0 (3 Reviews)
6 Bedrooms 14 Guests
Front Row to the Lake & Skyline: Epic 60th Flr 3BR
10.0 (3 Reviews)
3 Bedrooms 7 Guests
Grant Park 2BR Condo with Balcony Skyline View & Gym in Chicago Downtown
|
10.0 (1 Review)
2 Bedrooms 8 Guests
West Loop PH: Unmatched Views & Private Deck
10.0 (3 Reviews)
3 Bedrooms 8 Guests
Sky-High 3BR Penthouse in West Loop
10.0 (3 Reviews)
3 Bedrooms 8 Guests
Spacious Modern Pilsen Retreat Sleeps 8 Near Downtown Chicago
|
10.0 (1 Review)
3 Bedrooms 8 Guests
PH w/Bean & Lake Views, An Elite Stay
10.0 (2 Reviews)
3 Bedrooms 7 Guests
Luxury 2BD-2BA View-Gym-Rooftop
|
10.0 (1 Review)
2 Bedrooms 4 Guests
Deluxe River West PH for Unforgettable Memories
10.0 (2 Reviews)
3 Bedrooms 7 Guests
Scenic 3BR PH for Tourism + Prime Location
10.0 (2 Reviews)
3 Bedrooms 7 Guests
Prime 4BR Penthouse w/Skyline Views for Families
10.0 (2 Reviews)
4 Bedrooms 8 Guests
Stylish 2BR Retreat in Fulton Market for Getaways
10.0 (2 Reviews)
2 Bedrooms 5 Guests
High-End West Loop 2BR + City Views & Walkability
10.0 (2 Reviews)
2 Bedrooms 5 Guests
City Views + Walk to Dining, Ideal for All
10.0 (2 Reviews)
2 Bedrooms 5 Guests
United Center 3BD Apt with Parking and Balcony
10.0 (2 Reviews)
3 Bedrooms 6 Guests
Modern 3BR Stay Near DT CHI
FromR7,884 per night
|
10.0 (1 Review)
3 Bedrooms 6 Guests
The Langham, Chicago
FromR12,282 per night
|
9.8 (1003 Reviews)
1 Bedroom 2 Guests
High-End 2BR Apartments in West Loop
2.0 (1 Review)
8 Bedrooms 20 Guests
LIVN West Loop Chicago King Studio
|
10.0 (1 Review)
4 Bedrooms 2 Guests
The Penthouse at Grand Plaza
|
9.8 (26 Reviews)
1 Bedroom 2 Guests
Cultural Mile 2BR, A Stay in the Sky, 65th Floor
2.0 (1 Review)
2 Bedrooms 5 Guests
3BR Luxury Modern Apartment
FromR7,504 per night
|
10.0 (1 Review)
3 Bedrooms 8 Guests
Chicago Third Floor Studio by 747 Lofts
9.8 (7 Reviews)
1 Bedroom 1 Guest
Chic Fulton Market Oasis + Curated Comfort & Style
2.0 (1 Review)
2 Bedrooms 5 Guests
Stylish 3BR Gem in Prime Location
|
10.0 (1 Review)
1 Bedroom 8 Guests
Printer's Row 3BD Apt w/Pool, Roof, Deck, Parking
2.0 (1 Review)
3 Bedrooms 6 Guests
West Loop Balconied 2BR for Upscale Tours
2.0 (1 Review)
2 Bedrooms 5 Guests
Gym Garage Parking Balcony Sleeps 6
|
10.0 (1 Review)
2 Bedrooms 6 Guests
Premium Lake Views + Ideal for Group Getaways
New
7 Bedrooms 22 Guests
Luxury High-Floor Retreats + Lake Views
New
7 Bedrooms 17 Guests
4 Luxury 2BRs, Stay Together in Style, For Groups
New
6 Bedrooms 20 Guests
Modern 3BR Near McCormick & South Loop
|
10.0 (1 Review)
1 Bedroom 8 Guests
Exclusive Group Getaway in Vibrant West Loop
New
9 Bedrooms 22 Guests
S Loop Studio w Lounge Pool Gym nr Grant Park CHI-761
|
10.0 (1 Review)
1 Bedroom 2 Guests
2BRs w/Lakefront Views, Sleeps Large Groups
New
6 Bedrooms 15 Guests
Modern River West 2BR with W&D by Zencity
|
10.0 (1 Review)
2 Bedrooms 3 Guests
Prime Loop Apts + Convenience for Groups
New
8 Bedrooms 20 Guests

About Pilsen Vacation Rentals

With more than 3484 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 754.33 ft² on average, with prices averaging R6,687 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 3484 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 264
University Village / Little Italy Vacation Rentals in Chicago, Illinois 69
Lower West Side Vacation Rentals in Chicago, Illinois 37
Heart of Chicago Vacation Rentals in Chicago, Illinois 28