Chicago, Illinois

2018 21st Jack - New

4 bedrooms4 beds3.5 baths8 guestsNew

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.

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.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 26, 2026$343Available2
Jul 27, 2026$412Available2
Jul 28, 2026$470Available2
Jul 29, 2026$503Available2
Jul 30, 2026$1,149Available2
Jul 31, 2026$1,510Available2
Aug 1, 2026$1,567Available2
Aug 2, 2026$973Available2
Aug 3, 2026$403Available2
Aug 4, 2026$370Available2
Aug 5, 2026$350Available2
Aug 6, 2026$522Available2
Aug 7, 2026$865Available2
Aug 8, 2026$899Available2
Aug 9, 2026$351Available2
Aug 10, 2026$271Available2
Aug 11, 2026$278Available2
Aug 12, 2026$277Available2
Aug 13, 2026$472Available2
Aug 14, 2026$804Available2
Aug 15, 2026$855Available2
Aug 16, 2026$331Available2
Aug 17, 2026$257Available2
Aug 18, 2026$271Available2
Aug 19, 2026$259Available2
Aug 20, 2026$633Available2
Aug 21, 2026$849Available2
Aug 22, 2026$990Available2
Aug 23, 2026$354Available2
Aug 24, 2026$448Available2
Aug 25, 2026$477Available2
Aug 26, 2026$482Available2
Aug 27, 2026$616Available2
Aug 28, 2026$1,437Available2
Aug 29, 2026$1,482Available2
Aug 30, 2026$603Available2
Aug 31, 2026$271Available2
Sep 1, 2026$264Available2
Sep 2, 2026$261Available2
Sep 3, 2026$588Available2
Sep 4, 2026$1,386Available2
Sep 5, 2026$1,535Available2
Sep 6, 2026$851Available2
Sep 7, 2026$564Available2
Sep 8, 2026$329Available2
Sep 9, 2026$311Available2
Sep 10, 2026$407Available2
Sep 11, 2026$948Available2
Sep 12, 2026$1,096Available2
Sep 13, 2026$645Available2
Sep 14, 2026$698Available2
Sep 15, 2026$768Available2
Sep 16, 2026$766Available2
Sep 17, 2026$1,003Available2
Sep 18, 2026$1,434Available2
Sep 19, 2026$1,500Available2
Sep 20, 2026$748Available2
Sep 21, 2026$375Available2
Sep 22, 2026$375Available2
Sep 23, 2026$355Available2
Sep 24, 2026$445Available2
Sep 25, 2026$879Available2
Sep 26, 2026$1,012Available2
Sep 27, 2026$516Available2
Sep 28, 2026$497Available2
Sep 29, 2026$397Available2
Sep 30, 2026$375Available2
Oct 1, 2026$472Available2
Oct 2, 2026$1,195Available2
Oct 3, 2026$1,372Available2
Oct 4, 2026$680Available2
Oct 5, 2026$382Available2
Oct 6, 2026$723Available2
Oct 7, 2026$1,056Available2
Oct 8, 2026$1,355Available2
Oct 9, 2026$2,406Available2
Oct 10, 2026$2,678Available2
Oct 11, 2026$1,606Available2
Oct 12, 2026$801Available2
Oct 13, 2026$699Available2
Oct 14, 2026$567Available2
Oct 15, 2026$817Available2
Oct 16, 2026$1,314Available2
Oct 17, 2026$1,604Available2
Oct 18, 2026$800Available2
Oct 19, 2026$690Available2
Oct 20, 2026$714Available2
Oct 21, 2026$605Available2
Oct 22, 2026$702Available2
Oct 23, 2026$1,056Available2
Oct 24, 2026$964Available2

Amenities

Air conditioning
Carbon monoxide detector
Washer
Dryer
Free parking
Hot water
Baking sheet
Bed linens

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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

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

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.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 11:00 AM.
Maximum 8 guests.