Chicago, Illinois
2018 21st Jack - New
About the property
Discover one of Chicago's most vibrant neighborhoods from this stylish 4-bedroom retreat in vibrant Pilsen. Start your morning with coffee in a bright, welcoming space, spend the day exploring colorful murals, local galleries, and renowned restaurants, then gather with family and friends for a home-cooked meal. Ideally situated in Pilsen, the unit is only a quick drive or train ride away from downtown, making it the perfect home base for your Chicago adventure.
Interior Feeling:
This property is designed for relaxation and convenience. With ample living space, the area is perfect for groups. Enjoy a movie night in, share stories from the day, or simply enjoy quality time together.
- Bright and cozy living room with large windows.
- Plush seating perfect for movie nights or unwinding.
- Flat-screen TV for entertainment after a day of exploring.
Rest & Recharge:
Whether you're traveling with family, friends, or colleagues, everyone will have plenty of space to relax after a day in the city. Thoughtfully designed bedrooms and modern bathrooms help you feel refreshed and ready for tomorrow's adventures.
- Four comfortable bedrooms provide plenty of space for everyone.
- Three clean, modern bathrooms ensure privacy and convenience.
Delightful Dining:
We've equipped the kitchen for every occassion- from preparing breakfast before heading out or cooking dinner after a day of sightseeing, or preparing romantic dinners.
- Fully equipped kitchen with sleek stainless steel appliances.
- Rich wood cabinetry adds warmth to the space.
- Spacious island with seating for four, ideal for casual meals.
- Perfect for brewing morning coffee or preparing full dinners.
Impeccably Clean, Every Stay:
We believe a great stay begins with a spotless home. That's why at DreamRentals, cleanliness isn't just a priority—it's our standard. Every home is professionally cleaned, thoroughly sanitized, and carefully inspected before each guest arrives. From fresh linens to sparkling kitchens and sanitized bathrooms, we take pride in creating a home that feels as clean and inviting as your own.
DreamRentals Exclusive Perks:
Your stay with us includes access to exclusive discounts with our trusted local vendors! Elevate your Chicago experience with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Our team is here to help you create an unforgettable experience from start to finish!
Pets are welcome!
With a Walk Score around 90, Transit Score in the high 60s, and Bike Score near 78, it’s ideal for guests who prefer walking, biking, or easy access to the Pink Line and local buses. From Midway Airport, you can drive in about 20–30 minutes via I-55 N. By public transit, take the Orange Line to Roosevelt, transfer to the Pink Line, exit at 18th Station, and walk about 6 minutes west. From O’Hare Airport, driving takes about 40–60 minutes via I-90 E to I-55 S. For public transit, take the Blue Line to Clark/Lake, transfer to the Pink Line, exit at 18th Station, and walk west to the address.
Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.
No Smoking: For the comfort of all guests, smoking is strictly prohibited within the penthouse. Please smoke outside.
Pet Policy: We allow a maximum of 2 pets for a one time fee of $150
Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.
Maximum Occupancy: The maximum number of guests allowed in the penthouse is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.
Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.
Monitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.
Shared Housing Unit Operation License Number: 2823378
Registration Number: R25000130799
Privacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.
Support at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.
Feedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.
Our goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.
Discover one of Chicago's most vibrant neighborhoods from this stylish 4-bedroom retreat in vibrant Pilsen. Start your morning with coffee in a bright, welcoming space, spend the day exploring colorful murals, local galleries, and renowned restaurants, then gather with family and friends for a home-cooked meal. Ideally situated in Pilsen, the unit is only a quick drive or train ride away from downtown, making it the perfect home base for your Chicago adventure.
Interior Feeling:
This property is designed for relaxation and convenience. With ample living space, the area is perfect for groups. Enjoy a movie night in, share stories from the day, or simply enjoy quality time together.
- Bright and cozy living room with large windows.
- Plush seating perfect for movie nights or unwinding.
- Flat-screen TV for entertainment after a day of exploring.
Rest & Recharge:
Whether you're traveling with family, friends, or colleagues, everyone will have plenty of space to relax after a day in the city. Thoughtfully designed bedrooms and modern bathrooms help you feel refreshed and ready for tomorrow's adventures.
- Four comfortable bedrooms provide plenty of space for everyone.
- Three clean, modern bathrooms ensure privacy and convenience.
Delightful Dining:
We've equipped the kitchen for every occassion- from preparing breakfast before heading out or cooking dinner after a day of sightseeing, or preparing romantic dinners.
- Fully equipped kitchen with sleek stainless steel appliances.
- Rich wood cabinetry adds warmth to the space.
- Spacious island with seating for four, ideal for casual meals.
- Perfect for brewing morning coffee or preparing full dinners.
Impeccably Clean, Every Stay:
We believe a great stay begins with a spotless home. That's why at DreamRentals, cleanliness isn't just a priority—it's our standard. Every home is professionally cleaned, thoroughly sanitized, and carefully inspected before each guest arrives. From fresh linens to sparkling kitchens and sanitized bathrooms, we take pride in creating a home that feels as clean and inviting as your own.
DreamRentals Exclusive Perks:
Your stay with us includes access to exclusive discounts with our trusted local vendors! Elevate your Chicago experience with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Our team is here to help you create an unforgettable experience from start to finish!
Pets are welcome!
With a Walk Score around 90, Transit Score in the high 60s, and Bike Score near 78, it’s ideal for guests who prefer walking, biking, or easy access to the Pink Line and local buses. From Midway Airport, you can drive in about 20–30 minutes via I-55 N. By public transit, take the Orange Line to Roosevelt, transfer to the Pink Line, exit at 18th Station, and walk about 6 minutes west. From O’Hare Airport, driving takes about 40–60 minutes via I-90 E to I-55 S. For public transit, take the Blue Line to Clark/Lake, transfer to the Pink Line, exit at 18th Station, and walk west to the address.
Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.
No Smoking: For the comfort of all guests, smoking is strictly prohibited within the penthouse. Please smoke outside.
Pet Policy: We allow a maximum of 2 pets for a one time fee of $150
Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.
Maximum Occupancy: The maximum number of guests allowed in the penthouse is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.
Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.
Monitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.
Shared Housing Unit Operation License Number: 2823378
Registration Number: R25000130799
Privacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.
Support at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.
Feedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.
Our goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.
Discover one of Chicago's most vibrant neighborhoods from this stylish 4-bedroom retreat in vibrant Pilsen. Start your morning with coffee in a bright, welcoming space, spend the day exploring colorful murals, local galleries, and renowned restaurants, then gather with family and friends for a home-cooked meal. Ideally situated in Pilsen, the unit is only a quick drive or train ride away from downtown, making it the perfect home base for your Chicago adventure.
Interior Feeling:
This property is designed for relaxation and convenience. With ample living space, the area is perfect for groups. Enjoy a movie night in, share stories from the day, or simply enjoy quality time together.
- Bright and cozy living room with large windows.
- Plush seating perfect for movie nights or unwinding.
- Flat-screen TV for entertainment after a day of exploring.
Rest & Recharge:
Whether you're traveling with family, friends, or colleagues, everyone will have plenty of space to relax after a day in the city. Thoughtfully designed bedrooms and modern bathrooms help you feel refreshed and ready for tomorrow's adventures.
- Four comfortable bedrooms provide plenty of space for everyone.
- Three clean, modern bathrooms ensure privacy and convenience.
Delightful Dining:
We've equipped the kitchen for every occassion- from preparing breakfast before heading out or cooking dinner after a day of sightseeing, or preparing romantic dinners.
- Fully equipped kitchen with sleek stainless steel appliances.
- Rich wood cabinetry adds warmth to the space.
- Spacious island with seating for four, ideal for casual meals.
- Perfect for brewing morning coffee or preparing full dinners.
Impeccably Clean, Every Stay:
We believe a great stay begins with a spotless home. That's why at DreamRentals, cleanliness isn't just a priority—it's our standard. Every home is professionally cleaned, thoroughly sanitized, and carefully inspected before each guest arrives. From fresh linens to sparkling kitchens and sanitized bathrooms, we take pride in creating a home that feels as clean and inviting as your own.
DreamRentals Exclusive Perks:
Your stay with us includes access to exclusive discounts with our trusted local vendors! Elevate your Chicago experience with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Our team is here to help you create an unforgettable experience from start to finish!
Pets are welcome!
With a Walk Score around 90, Transit Score in the high 60s, and Bike Score near 78, it’s ideal for guests who prefer walking, biking, or easy access to the Pink Line and local buses. From Midway Airport, you can drive in about 20–30 minutes via I-55 N. By public transit, take the Orange Line to Roosevelt, transfer to the Pink Line, exit at 18th Station, and walk about 6 minutes west. From O’Hare Airport, driving takes about 40–60 minutes via I-90 E to I-55 S. For public transit, take the Blue Line to Clark/Lake, transfer to the Pink Line, exit at 18th Station, and walk west to the address.
Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.
No Smoking: For the comfort of all guests, smoking is strictly prohibited within the penthouse. Please smoke outside.
Pet Policy: We allow a maximum of 2 pets for a one time fee of $150
Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.
Maximum Occupancy: The maximum number of guests allowed in the penthouse is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.
Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.
Monitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.
Shared Housing Unit Operation License Number: 2823378
Registration Number: R25000130799
Privacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.
Support at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.
Feedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.
Our goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.
Availability & Pricing
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 26, 2026 | $343 | Available | 2 |
| Jul 27, 2026 | $412 | Available | 2 |
| Jul 28, 2026 | $470 | Available | 2 |
| Jul 29, 2026 | $503 | Available | 2 |
| Jul 30, 2026 | $1,149 | Available | 2 |
| Jul 31, 2026 | $1,510 | Available | 2 |
| Aug 1, 2026 | $1,567 | Available | 2 |
| Aug 2, 2026 | $973 | Available | 2 |
| Aug 3, 2026 | $403 | Available | 2 |
| Aug 4, 2026 | $370 | Available | 2 |
| Aug 5, 2026 | $350 | Available | 2 |
| Aug 6, 2026 | $522 | Available | 2 |
| Aug 7, 2026 | $865 | Available | 2 |
| Aug 8, 2026 | $899 | Available | 2 |
| Aug 9, 2026 | $351 | Available | 2 |
| Aug 10, 2026 | $271 | Available | 2 |
| Aug 11, 2026 | $278 | Available | 2 |
| Aug 12, 2026 | $277 | Available | 2 |
| Aug 13, 2026 | $472 | Available | 2 |
| Aug 14, 2026 | $804 | Available | 2 |
| Aug 15, 2026 | $855 | Available | 2 |
| Aug 16, 2026 | $331 | Available | 2 |
| Aug 17, 2026 | $257 | Available | 2 |
| Aug 18, 2026 | $271 | Available | 2 |
| Aug 19, 2026 | $259 | Available | 2 |
| Aug 20, 2026 | $633 | Available | 2 |
| Aug 21, 2026 | $849 | Available | 2 |
| Aug 22, 2026 | $990 | Available | 2 |
| Aug 23, 2026 | $354 | Available | 2 |
| Aug 24, 2026 | $448 | Available | 2 |
| Aug 25, 2026 | $477 | Available | 2 |
| Aug 26, 2026 | $482 | Available | 2 |
| Aug 27, 2026 | $616 | Available | 2 |
| Aug 28, 2026 | $1,437 | Available | 2 |
| Aug 29, 2026 | $1,482 | Available | 2 |
| Aug 30, 2026 | $603 | Available | 2 |
| Aug 31, 2026 | $271 | Available | 2 |
| Sep 1, 2026 | $264 | Available | 2 |
| Sep 2, 2026 | $261 | Available | 2 |
| Sep 3, 2026 | $588 | Available | 2 |
| Sep 4, 2026 | $1,386 | Available | 2 |
| Sep 5, 2026 | $1,535 | Available | 2 |
| Sep 6, 2026 | $851 | Available | 2 |
| Sep 7, 2026 | $564 | Available | 2 |
| Sep 8, 2026 | $329 | Available | 2 |
| Sep 9, 2026 | $311 | Available | 2 |
| Sep 10, 2026 | $407 | Available | 2 |
| Sep 11, 2026 | $948 | Available | 2 |
| Sep 12, 2026 | $1,096 | Available | 2 |
| Sep 13, 2026 | $645 | Available | 2 |
| Sep 14, 2026 | $698 | Available | 2 |
| Sep 15, 2026 | $768 | Available | 2 |
| Sep 16, 2026 | $766 | Available | 2 |
| Sep 17, 2026 | $1,003 | Available | 2 |
| Sep 18, 2026 | $1,434 | Available | 2 |
| Sep 19, 2026 | $1,500 | Available | 2 |
| Sep 20, 2026 | $748 | Available | 2 |
| Sep 21, 2026 | $375 | Available | 2 |
| Sep 22, 2026 | $375 | Available | 2 |
| Sep 23, 2026 | $355 | Available | 2 |
| Sep 24, 2026 | $445 | Available | 2 |
| Sep 25, 2026 | $879 | Available | 2 |
| Sep 26, 2026 | $1,012 | Available | 2 |
| Sep 27, 2026 | $516 | Available | 2 |
| Sep 28, 2026 | $497 | Available | 2 |
| Sep 29, 2026 | $397 | Available | 2 |
| Sep 30, 2026 | $375 | Available | 2 |
| Oct 1, 2026 | $472 | Available | 2 |
| Oct 2, 2026 | $1,195 | Available | 2 |
| Oct 3, 2026 | $1,372 | Available | 2 |
| Oct 4, 2026 | $680 | Available | 2 |
| Oct 5, 2026 | $382 | Available | 2 |
| Oct 6, 2026 | $723 | Available | 2 |
| Oct 7, 2026 | $1,056 | Available | 2 |
| Oct 8, 2026 | $1,355 | Available | 2 |
| Oct 9, 2026 | $2,406 | Available | 2 |
| Oct 10, 2026 | $2,678 | Available | 2 |
| Oct 11, 2026 | $1,606 | Available | 2 |
| Oct 12, 2026 | $801 | Available | 2 |
| Oct 13, 2026 | $699 | Available | 2 |
| Oct 14, 2026 | $567 | Available | 2 |
| Oct 15, 2026 | $817 | Available | 2 |
| Oct 16, 2026 | $1,314 | Available | 2 |
| Oct 17, 2026 | $1,604 | Available | 2 |
| Oct 18, 2026 | $800 | Available | 2 |
| Oct 19, 2026 | $690 | Available | 2 |
| Oct 20, 2026 | $714 | Available | 2 |
| Oct 21, 2026 | $605 | Available | 2 |
| Oct 22, 2026 | $702 | Available | 2 |
| Oct 23, 2026 | $1,056 | Available | 2 |
| Oct 24, 2026 | $964 | Available | 2 |
Amenities
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Where you'll be
Chicago, Illinois, 60608, United States
Experience the dynamic pulse of Chicago from a base that puts the city’s architectural marvels and cultural treasures within easy reach. Discover soaring views from the Skydeck Chicago at Willis Tower, or take a short drive to Millennium Park to see the iconic public art installations. Enrich your stay by exploring the historic galleries of The Art Institute of Chicago or visiting the world-renowned exhibits at the Field Museum
Experience the dynamic pulse of Chicago from a base that puts the city’s architectural marvels and cultural treasures within easy reach. Discover soaring views from the Skydeck Chicago at Willis Tower, or take a short drive to Millennium Park to see the iconic public art installations. Enrich your stay by exploring the historic galleries of The Art Institute of Chicago or visiting the world-renowned exhibits at the Field Museum
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.
Things to know
Cancellation policy
Contact us for cancellation policy details prior to booking.
Payment processing fee and a 3% booking fee is non refundable upon cancellation.