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