# Milwaukee Ave – 3 Bedroom Vacation Rental in Chicago, Illinois | Dream Rentals 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. **Property URL**: https://dreamrentals.wanderos.com/property/652663392355483649/milwaukee-ave **Markdown URL**: https://dreamrentals.wanderos.com/property/652663392355483649/milwaukee-ave.md ## Property Overview - **Sleeps**: 14 guests - **Bedrooms**: 3 bedrooms - **Bathrooms**: 3 - **Square Footage**: 1,500 sq ft ## Pricing & Availability - **Nightly Rate**: $312 - $2,941 (before taxes and fees) - **Next Available**: Jul 27, 2026 - **Available Days**: 90 days in the next 90 days - **Daily Pricing (Next 90 Days)**: - Jul 26, 2026: $412 (Available) (2 night min) - Jul 27, 2026: $312 (Available) (2 night min) - Jul 28, 2026: $488 (Available) (2 night min) - Jul 29, 2026: $546 (Available) (2 night min) - Jul 30, 2026: $1,445 (Available) (2 night min) - Jul 31, 2026: $1,922 (Available) (2 night min) - Aug 1, 2026: $2,121 (Available) (2 night min) - Aug 2, 2026: $1,222 (Available) (2 night min) - Aug 3, 2026: $551 (Available) (2 night min) - Aug 4, 2026: $383 (Available) (2 night min) - Aug 5, 2026: $426 (Available) (2 night min) - Aug 6, 2026: $651 (Available) (2 night min) - Aug 7, 2026: $1,232 (Available) (2 night min) - Aug 8, 2026: $1,352 (Available) (2 night min) - Aug 9, 2026: $469 (Available) (2 night min) - Aug 10, 2026: $387 (Available) (2 night min) - Aug 11, 2026: $359 (Available) (2 night min) - Aug 12, 2026: $355 (Available) (2 night min) - Aug 13, 2026: $612 (Available) (2 night min) - Aug 14, 2026: $1,140 (Available) (2 night min) - Aug 15, 2026: $1,250 (Available) (2 night min) - Aug 16, 2026: $418 (Available) (2 night min) - Aug 17, 2026: $339 (Available) (2 night min) - Aug 18, 2026: $330 (Available) (2 night min) - Aug 19, 2026: $336 (Available) (2 night min) - Aug 20, 2026: $799 (Available) (2 night min) - Aug 21, 2026: $1,131 (Available) (2 night min) - Aug 22, 2026: $1,263 (Available) (2 night min) - Aug 23, 2026: $445 (Available) (2 night min) - Aug 24, 2026: $343 (Available) (2 night min) - Aug 25, 2026: $485 (Available) (2 night min) - Aug 26, 2026: $497 (Available) (2 night min) - Aug 27, 2026: $739 (Available) (2 night min) - Aug 28, 2026: $1,704 (Available) (2 night min) - Aug 29, 2026: $1,818 (Available) (2 night min) - Aug 30, 2026: $696 (Available) (2 night min) - Aug 31, 2026: $365 (Available) (2 night min) - Sep 1, 2026: $354 (Available) (2 night min) - Sep 2, 2026: $336 (Available) (2 night min) - Sep 3, 2026: $715 (Available) (2 night min) - Sep 4, 2026: $1,609 (Available) (2 night min) - Sep 5, 2026: $1,784 (Available) (2 night min) - Sep 6, 2026: $914 (Available) (2 night min) - Sep 7, 2026: $776 (Available) (2 night min) - Sep 8, 2026: $626 (Available) (2 night min) - Sep 9, 2026: $415 (Available) (2 night min) - Sep 10, 2026: $547 (Available) (2 night min) - Sep 11, 2026: $1,195 (Available) (2 night min) - Sep 12, 2026: $1,367 (Available) (2 night min) - Sep 13, 2026: $674 (Available) (2 night min) - Sep 14, 2026: $625 (Available) (2 night min) - Sep 15, 2026: $709 (Available) (2 night min) - Sep 16, 2026: $662 (Available) (2 night min) - Sep 17, 2026: $930 (Available) (2 night min) - Sep 18, 2026: $1,554 (Available) (2 night min) - Sep 19, 2026: $1,687 (Available) (2 night min) - Sep 20, 2026: $772 (Available) (2 night min) - Sep 21, 2026: $404 (Available) (2 night min) - Sep 22, 2026: $404 (Available) (2 night min) - Sep 23, 2026: $383 (Available) (2 night min) - Sep 24, 2026: $562 (Available) (2 night min) - Sep 25, 2026: $1,258 (Available) (2 night min) - Sep 26, 2026: $1,390 (Available) (2 night min) - Sep 27, 2026: $669 (Available) (2 night min) - Sep 28, 2026: $596 (Available) (2 night min) - Sep 29, 2026: $472 (Available) (2 night min) - Sep 30, 2026: $446 (Available) (2 night min) - Oct 1, 2026: $556 (Available) (2 night min) - Oct 2, 2026: $1,606 (Available) (2 night min) - Oct 3, 2026: $1,820 (Available) (2 night min) - Oct 4, 2026: $836 (Available) (2 night min) - Oct 5, 2026: $826 (Available) (2 night min) - Oct 6, 2026: $932 (Available) (2 night min) - Oct 7, 2026: $1,372 (Available) (2 night min) - Oct 8, 2026: $1,796 (Available) (2 night min) - Oct 9, 2026: $2,641 (Available) (2 night min) - Oct 10, 2026: $2,941 (Available) (2 night min) - Oct 11, 2026: $1,819 (Available) (2 night min) - Oct 12, 2026: $1,052 (Available) (2 night min) - Oct 13, 2026: $826 (Available) (2 night min) - Oct 14, 2026: $722 (Available) (2 night min) - Oct 15, 2026: $829 (Available) (2 night min) - Oct 16, 2026: $1,646 (Available) (2 night min) - Oct 17, 2026: $1,865 (Available) (2 night min) - Oct 18, 2026: $846 (Available) (2 night min) - Oct 19, 2026: $488 (Available) (2 night min) - Oct 20, 2026: $665 (Available) (2 night min) - Oct 21, 2026: $648 (Available) (2 night min) - Oct 22, 2026: $842 (Available) (2 night min) - Oct 23, 2026: $1,198 (Available) (2 night min) - Oct 24, 2026: $1,333 (Available) (2 night min) ## Availability Rules 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 listed minimum stay, and no intervening nights are marked "Not Available". - Prices are nightly rates before taxes and fees. Final checkout pricing may include taxes, fees, add-ons, discounts, and payment terms. - If a requested date range extends beyond the 90-day table, visit the property URL for live booking details. ## Stay Timing - **Check-in**: After 4:00 PM - **Check-out**: Before 11:00 AM ## Location - **Address**: Chicago, Illinois, United States of America - **Postal Code**: 60622 - **Coordinates**: 41.90966, -87.676048 - **Local Area**: 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 ## Sleeping Arrangements ### Bedroom 1 KING BED ### Bedroom 2 KING BED, FULL BED, FULL BED ### Bedroom 3 KING BED, FULL BED, FULL BED ### Bedroom 4 FULL BED ## Amenities - FIRE_PLACE - PATIO - ELEVATOR - AIR_CONDITIONING - CARBON_MONOXIDE_DETECTOR - WASHER - DRYER - FIRE_EXTINGUISHER - FIRST_AID_KIT - FREE_PARKING - HOT_WATER - Casinos - Cleaning products - Essentials - Golf - Optional - Museums - Shopping - BBQ_UTENSILS - BED_LINENS - BLENDER - BODY_SOAP - CEILING_FAN - CITY_VIEW - COFFEE - COFFEE_MAKER - CONDITIONER - COOKING_BASICS - BICYCLE - DEDICATED_WORKSPACE - DINING_TABLE - DISHES - FREEZER - GARAGE - HANGERS - HEATING - ICE_MAKER - WIFI - IRON - KETTLE - KITCHEN - LONG_TERM_STAYS_ALLOWED - MICROWAVE - OVEN - PAID_PARKING - FRIDGE - SAFE - SHAMPOO - SHOWER_GEL - SMOKE_DETECTOR - TV - BATH_LINENS - BODY_SOAP - SHOWER_GEL - CONDITIONER - BATH_LINENS - SHAMPOO - PATIO - BBQ_UTENSILS - BLENDER - COFFEE - COFFEE_MAKER - COOKING_BASICS - DISHES - FREEZER - ICE_MAKER - KETTLE - KITCHEN - MICROWAVE - OVEN - FRIDGE - FIRE_PLACE - CEILING_FAN - HEATING - TV - ELEVATOR - CITY_VIEW - BICYCLE - GARAGE - PAID_PARKING - DEDICATED_WORKSPACE - DINING_TABLE - WIFI - LONG_TERM_STAYS_ALLOWED - SMOKE_DETECTOR - IRON - BED_LINENS - HANGERS - SAFE ## Guest Services - **24/7 Concierge**: Available through the Dream Rentals app - **Housekeeping**: Professional cleaning service - **Maintenance**: On-call support for any issues - **Local Recommendations**: Dining, activities, and experiences ## Property Details - **Property ID**: 652663392355483649 - **Property Slug**: milwaukee-ave ## Booking Information For more information and to book this property, visit: https://dreamrentals.wanderos.com/property/652663392355483649/milwaukee-ave Or contact Dream Rentals customer service for assistance. --- *Last modified: Jul 26, 2026* *This markdown file is generated automatically for AI agents and search engines.*