# 2018 21st Jack - New – 4 Bedroom Vacation Rental in Chicago, Illinois | Dream Rentals 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. **Property URL**: https://dreamrentals.wanderos.com/property/652664862236740135/2018-21st-jack-new **Markdown URL**: https://dreamrentals.wanderos.com/property/652664862236740135/2018-21st-jack-new.md ## Property Overview - **Sleeps**: 8 guests - **Bedrooms**: 4 bedrooms - **Bathrooms**: 3.5 - **Square Footage**: 1,000 sq ft - **Pet Friendly**: Yes ## Pricing & Availability - **Nightly Rate**: $257 - $2,678 (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: $343 (Available) (2 night min) - Jul 27, 2026: $412 (Available) (2 night min) - Jul 28, 2026: $470 (Available) (2 night min) - Jul 29, 2026: $503 (Available) (2 night min) - Jul 30, 2026: $1,149 (Available) (2 night min) - Jul 31, 2026: $1,510 (Available) (2 night min) - Aug 1, 2026: $1,567 (Available) (2 night min) - Aug 2, 2026: $973 (Available) (2 night min) - Aug 3, 2026: $403 (Available) (2 night min) - Aug 4, 2026: $370 (Available) (2 night min) - Aug 5, 2026: $350 (Available) (2 night min) - Aug 6, 2026: $522 (Available) (2 night min) - Aug 7, 2026: $865 (Available) (2 night min) - Aug 8, 2026: $899 (Available) (2 night min) - Aug 9, 2026: $351 (Available) (2 night min) - Aug 10, 2026: $271 (Available) (2 night min) - Aug 11, 2026: $278 (Available) (2 night min) - Aug 12, 2026: $277 (Available) (2 night min) - Aug 13, 2026: $472 (Available) (2 night min) - Aug 14, 2026: $804 (Available) (2 night min) - Aug 15, 2026: $855 (Available) (2 night min) - Aug 16, 2026: $331 (Available) (2 night min) - Aug 17, 2026: $257 (Available) (2 night min) - Aug 18, 2026: $271 (Available) (2 night min) - Aug 19, 2026: $259 (Available) (2 night min) - Aug 20, 2026: $633 (Available) (2 night min) - Aug 21, 2026: $849 (Available) (2 night min) - Aug 22, 2026: $990 (Available) (2 night min) - Aug 23, 2026: $354 (Available) (2 night min) - Aug 24, 2026: $448 (Available) (2 night min) - Aug 25, 2026: $477 (Available) (2 night min) - Aug 26, 2026: $482 (Available) (2 night min) - Aug 27, 2026: $616 (Available) (2 night min) - Aug 28, 2026: $1,437 (Available) (2 night min) - Aug 29, 2026: $1,482 (Available) (2 night min) - Aug 30, 2026: $603 (Available) (2 night min) - Aug 31, 2026: $271 (Available) (2 night min) - Sep 1, 2026: $264 (Available) (2 night min) - Sep 2, 2026: $261 (Available) (2 night min) - Sep 3, 2026: $588 (Available) (2 night min) - Sep 4, 2026: $1,386 (Available) (2 night min) - Sep 5, 2026: $1,535 (Available) (2 night min) - Sep 6, 2026: $851 (Available) (2 night min) - Sep 7, 2026: $564 (Available) (2 night min) - Sep 8, 2026: $329 (Available) (2 night min) - Sep 9, 2026: $311 (Available) (2 night min) - Sep 10, 2026: $407 (Available) (2 night min) - Sep 11, 2026: $948 (Available) (2 night min) - Sep 12, 2026: $1,096 (Available) (2 night min) - Sep 13, 2026: $645 (Available) (2 night min) - Sep 14, 2026: $698 (Available) (2 night min) - Sep 15, 2026: $768 (Available) (2 night min) - Sep 16, 2026: $766 (Available) (2 night min) - Sep 17, 2026: $1,003 (Available) (2 night min) - Sep 18, 2026: $1,434 (Available) (2 night min) - Sep 19, 2026: $1,500 (Available) (2 night min) - Sep 20, 2026: $748 (Available) (2 night min) - Sep 21, 2026: $375 (Available) (2 night min) - Sep 22, 2026: $375 (Available) (2 night min) - Sep 23, 2026: $355 (Available) (2 night min) - Sep 24, 2026: $445 (Available) (2 night min) - Sep 25, 2026: $879 (Available) (2 night min) - Sep 26, 2026: $1,012 (Available) (2 night min) - Sep 27, 2026: $516 (Available) (2 night min) - Sep 28, 2026: $497 (Available) (2 night min) - Sep 29, 2026: $397 (Available) (2 night min) - Sep 30, 2026: $375 (Available) (2 night min) - Oct 1, 2026: $472 (Available) (2 night min) - Oct 2, 2026: $1,195 (Available) (2 night min) - Oct 3, 2026: $1,372 (Available) (2 night min) - Oct 4, 2026: $680 (Available) (2 night min) - Oct 5, 2026: $382 (Available) (2 night min) - Oct 6, 2026: $723 (Available) (2 night min) - Oct 7, 2026: $1,056 (Available) (2 night min) - Oct 8, 2026: $1,355 (Available) (2 night min) - Oct 9, 2026: $2,406 (Available) (2 night min) - Oct 10, 2026: $2,678 (Available) (2 night min) - Oct 11, 2026: $1,606 (Available) (2 night min) - Oct 12, 2026: $801 (Available) (2 night min) - Oct 13, 2026: $699 (Available) (2 night min) - Oct 14, 2026: $567 (Available) (2 night min) - Oct 15, 2026: $817 (Available) (2 night min) - Oct 16, 2026: $1,314 (Available) (2 night min) - Oct 17, 2026: $1,604 (Available) (2 night min) - Oct 18, 2026: $800 (Available) (2 night min) - Oct 19, 2026: $690 (Available) (2 night min) - Oct 20, 2026: $714 (Available) (2 night min) - Oct 21, 2026: $605 (Available) (2 night min) - Oct 22, 2026: $702 (Available) (2 night min) - Oct 23, 2026: $1,056 (Available) (2 night min) - Oct 24, 2026: $964 (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 - **Postal Code**: 60608 - **Coordinates**: 41.8532982, -87.676688 - **Local Area**: 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 ## Sleeping Arrangements ### Bedroom 1 KING BED ### Bedroom 2 KING BED ### Bedroom 3 QUEEN BED ### Bedroom 4 QUEEN BED ## Amenities - AIR_CONDITIONING - CARBON_MONOXIDE_DETECTOR - WASHER - DRYER - FREE_PARKING - HOT_WATER - Casinos - Cleaning products - Downtown - Emergency exit - Essentials - Golf - Optional - Museums - Pets allowed - Private entrance - Shopping - Suitable for children (2-12 years) - Suitable for infants (under 2 years) - Zoo - BAKING_SHEET - BED_LINENS - BODY_SOAP - CEILING_FAN - COFFEE - COFFEE_MAKER - CONDITIONER - COOKING_BASICS - DINING_TABLE - DISHES - EXTRA_PILLOWS - FREEZER - HANGERS - HEATING - WIFI - IRON - KITCHEN - LONG_TERM_STAYS_ALLOWED - LUGGAGE_DROP_OFF_ALLOWED - MICROWAVE - OVEN - PAID_PARKING - FRIDGE - SHAMPOO - SHOWER_GEL - SMOKE_DETECTOR - STOVE - TV - TOASTER - BATH_LINENS - WINE_GLASSES - BODY_SOAP - SHOWER_GEL - CONDITIONER - BATH_LINENS - SHAMPOO - BAKING_SHEET - COFFEE - COFFEE_MAKER - COOKING_BASICS - DISHES - FREEZER - KITCHEN - MICROWAVE - OVEN - FRIDGE - STOVE - TOASTER - WINE_GLASSES - CEILING_FAN - HEATING - TV - DINING_TABLE - WIFI - LONG_TERM_STAYS_ALLOWED - SMOKE_DETECTOR - IRON - LUGGAGE_DROP_OFF_ALLOWED - PAID_PARKING - BED_LINENS - EXTRA_PILLOWS - HANGERS ## 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**: 652664862236740135 - **Property Slug**: 2018-21st-jack-new ## Booking Information For more information and to book this property, visit: https://dreamrentals.wanderos.com/property/652664862236740135/2018-21st-jack-new 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.*