Chicago, Illinois

Milwaukee Ave

3 bedrooms8 beds3 baths14 guestsNew

About the property

Experience city living in this stylish 3BD/3BA duplex penthouse in the heart of Wicker Park! Just a 2-minute walk to the Damen Blue Line, top restaurants, bars, boutiques, and live music. Explore the neighborhood by day, then unwind with skyline views from two private decks, soak in the hot tub, cool off in the cold plunge, or gather around the fire pit. With three king bedrooms, two living rooms, a chef's kitchen, and a private elevator, this is city living at its finest.

Interior Feeling:
Designed with comfort and style in mind, this architecturally beautiful penthouse features soaring 12-foot ceilings and abundant natural light, making it a perfect retreat for those seeking the best of city living.

  • Two spacious living rooms for relaxation and entertainment
  • Private elevator opens to a bright living room
  • Abundant natural light from large windows
  • Wet bar for entertaining
  • Curated local artwork throughout the unit

Prioritizing your Comfort:

  • Three bedrooms for a restful stay
  • Two master suites, each with a large private bath
  • A third spacious bedroom with a king bed and full bath across the hall
  • All bedrooms feature king-size pillow-top beds for maximum comfort
  • Additional sleeping options include double bunk beds adjacent to each master suite and a queen-size loft bed on the second floor near the second living room for a total of 14 guests to sleep

Delightful Dining:
End the day with a home cooked meal using our fully equipped kitchen.

  • Fully equipped kitchen with utensils and cookware
  • Spacious dining areas for family meals or entertaining guests

Outdoor Bliss:
Step outside and enjoy your own private backyard retreat. Whether you're grilling dinner, gathering with friends, or simply relaxing after a busy day, this outdoor space is designed for making memories.

  • Two large decks offering breathtaking views of the Chicago skyline
  • Private patio with outdoor seating
  • Built-in grill for outdoor cooking
  • Cozy fire pit for evening gatherings

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!

Getting around is effortless with the CTA Blue Line and multiple bus routes just a short walk away, providing quick access to Downtown Chicago and O'Hare International Airport. Popular attractions including Millennium Park, the Magnificent Mile, Navy Pier, the Art Institute of Chicago, and the United Center are all within a 10–20 minute drive or transit ride. Midway International Airport is typically 25–35 minutes away by car, making this an ideal location for both business and leisure travelers.

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 adore pets, but unfortunately, the penthouse is not pet-friendly. We appreciate your understanding in adhering to this policy.

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.

Registration number: R22000094766
Shared Housing Unit Operation License Number: 2823378

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.

Experience city living in this stylish 3BD/3BA duplex penthouse in the heart of Wicker Park! Just a 2-minute walk to the Damen Blue Line, top restaurants, bars, boutiques, and live music. Explore the neighborhood by day, then unwind with skyline views from two private decks, soak in the hot tub, cool off in the cold plunge, or gather around the fire pit. With three king bedrooms, two living rooms, a chef's kitchen, and a private elevator, this is city living at its finest.

Interior Feeling:
Designed with comfort and style in mind, this architecturally beautiful penthouse features soaring 12-foot ceilings and abundant natural light, making it a perfect retreat for those seeking the best of city living.

  • Two spacious living rooms for relaxation and entertainment
  • Private elevator opens to a bright living room
  • Abundant natural light from large windows
  • Wet bar for entertaining
  • Curated local artwork throughout the unit

Prioritizing your Comfort:

  • Three bedrooms for a restful stay
  • Two master suites, each with a large private bath
  • A third spacious bedroom with a king bed and full bath across the hall
  • All bedrooms feature king-size pillow-top beds for maximum comfort
  • Additional sleeping options include double bunk beds adjacent to each master suite and a queen-size loft bed on the second floor near the second living room for a total of 14 guests to sleep

Delightful Dining:
End the day with a home cooked meal using our fully equipped kitchen.

  • Fully equipped kitchen with utensils and cookware
  • Spacious dining areas for family meals or entertaining guests

Outdoor Bliss:
Step outside and enjoy your own private backyard retreat. Whether you're grilling dinner, gathering with friends, or simply relaxing after a busy day, this outdoor space is designed for making memories.

  • Two large decks offering breathtaking views of the Chicago skyline
  • Private patio with outdoor seating
  • Built-in grill for outdoor cooking
  • Cozy fire pit for evening gatherings

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!

Getting around is effortless with the CTA Blue Line and multiple bus routes just a short walk away, providing quick access to Downtown Chicago and O'Hare International Airport. Popular attractions including Millennium Park, the Magnificent Mile, Navy Pier, the Art Institute of Chicago, and the United Center are all within a 10–20 minute drive or transit ride. Midway International Airport is typically 25–35 minutes away by car, making this an ideal location for both business and leisure travelers.

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 adore pets, but unfortunately, the penthouse is not pet-friendly. We appreciate your understanding in adhering to this policy.

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.

Registration number: R22000094766
Shared Housing Unit Operation License Number: 2823378

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$412Available2
Jul 27, 2026$312Available2
Jul 28, 2026$488Available2
Jul 29, 2026$546Available2
Jul 30, 2026$1,445Available2
Jul 31, 2026$1,922Available2
Aug 1, 2026$2,121Available2
Aug 2, 2026$1,222Available2
Aug 3, 2026$551Available2
Aug 4, 2026$383Available2
Aug 5, 2026$426Available2
Aug 6, 2026$651Available2
Aug 7, 2026$1,232Available2
Aug 8, 2026$1,352Available2
Aug 9, 2026$469Available2
Aug 10, 2026$387Available2
Aug 11, 2026$359Available2
Aug 12, 2026$355Available2
Aug 13, 2026$612Available2
Aug 14, 2026$1,140Available2
Aug 15, 2026$1,250Available2
Aug 16, 2026$418Available2
Aug 17, 2026$339Available2
Aug 18, 2026$330Available2
Aug 19, 2026$336Available2
Aug 20, 2026$799Available2
Aug 21, 2026$1,131Available2
Aug 22, 2026$1,263Available2
Aug 23, 2026$445Available2
Aug 24, 2026$343Available2
Aug 25, 2026$485Available2
Aug 26, 2026$497Available2
Aug 27, 2026$739Available2
Aug 28, 2026$1,704Available2
Aug 29, 2026$1,818Available2
Aug 30, 2026$696Available2
Aug 31, 2026$365Available2
Sep 1, 2026$354Available2
Sep 2, 2026$336Available2
Sep 3, 2026$715Available2
Sep 4, 2026$1,609Available2
Sep 5, 2026$1,784Available2
Sep 6, 2026$914Available2
Sep 7, 2026$776Available2
Sep 8, 2026$626Available2
Sep 9, 2026$415Available2
Sep 10, 2026$547Available2
Sep 11, 2026$1,195Available2
Sep 12, 2026$1,367Available2
Sep 13, 2026$674Available2
Sep 14, 2026$625Available2
Sep 15, 2026$709Available2
Sep 16, 2026$662Available2
Sep 17, 2026$930Available2
Sep 18, 2026$1,554Available2
Sep 19, 2026$1,687Available2
Sep 20, 2026$772Available2
Sep 21, 2026$404Available2
Sep 22, 2026$404Available2
Sep 23, 2026$383Available2
Sep 24, 2026$562Available2
Sep 25, 2026$1,258Available2
Sep 26, 2026$1,390Available2
Sep 27, 2026$669Available2
Sep 28, 2026$596Available2
Sep 29, 2026$472Available2
Sep 30, 2026$446Available2
Oct 1, 2026$556Available2
Oct 2, 2026$1,606Available2
Oct 3, 2026$1,820Available2
Oct 4, 2026$836Available2
Oct 5, 2026$826Available2
Oct 6, 2026$932Available2
Oct 7, 2026$1,372Available2
Oct 8, 2026$1,796Available2
Oct 9, 2026$2,641Available2
Oct 10, 2026$2,941Available2
Oct 11, 2026$1,819Available2
Oct 12, 2026$1,052Available2
Oct 13, 2026$826Available2
Oct 14, 2026$722Available2
Oct 15, 2026$829Available2
Oct 16, 2026$1,646Available2
Oct 17, 2026$1,865Available2
Oct 18, 2026$846Available2
Oct 19, 2026$488Available2
Oct 20, 2026$665Available2
Oct 21, 2026$648Available2
Oct 22, 2026$842Available2
Oct 23, 2026$1,198Available2
Oct 24, 2026$1,333Available2

Amenities

Fire place
Patio
Elevator
Air conditioning
Carbon monoxide detector
Washer
Dryer
Fire extinguisher

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Where you'll be

Chicago, Illinois, 60622, United States of America

Discover the dynamic rhythm of Chicago from a location that balances urban sophistication with proximity to the city's most iconic landmarks. Explore the sprawling grounds of Lincoln Park Zoo or take a short drive to experience breathtaking panoramic views from the observation decks at 360 CHICAGO and the famous Skydeck Chicago at Willis Tower. Catch a historic game at Wrigley Field or savor artisanal blends at the Starbucks Reserve Roastery, all

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

Not suitable for children (2–12 years).
Not suitable for infants (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 11:00 AM.
Maximum 14 guests.