Holiday rentals with a hot tub in Downtown Chicago

Luxury Penthouse w/ HOT TUB & Amazing Roof Deck

Look no further for your luxury Chicago getaway. In the heart of Wicker Park, our condo is just blocks away from fantastic restaurants, shops, and nightlife on Division and Milwaukee, and just a block from the Division El Stop - Be downtown in just 10 minutes! The unit comes with a fully equipped kitchen, bathroom amenities, smart TVs in each room, high-speed internet and direct roof-top access. Relax after a long day of exploring Chicago in the rooftop hot tub overlooking the Chicago skyline.

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

*Due to AirBnB new changes in fee disclosure, 18% of the daily rate you see goes to Airbnb* 1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (2 Queens) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. A parking space in the rear allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions. NO CHORES!

Tea Studio in Wicker Park Spring Factory

There's no other place like it in Chicago. A converted 1900's warehouse in the heart of Wicker Park - Once a Prohibition-era distillery, then a spring factory, and finally reimagined as a one-of-a-kind designer loft. Features soaring 14-foot timber ceilings, exposed brick, and a level of finish that earned a national kitchen award and a feature in TimeOut's "Best in Chicago". The kitchen is massive. The bathrooms are luxurious. Plus, Chicago's best neighborhood is right outside the door.

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets are Allowed!

Level Studio | Fulton Market

Our Level Suite, approximately 500 sqft, features an open concept studio layout with fully equipped kitchen with gas cooktop, comfortable living area, king or queen bed, storage closet, and private balcony. Many of the suites also feature designated workspaces and sofa beds. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, complimentary Wi-Fi and local calling.

Ukrainian Village 3BR/3BA • Private Patio, Parking

Welcome to Ohio St — a beautifully designed 3-bedroom, 3-bathroom private home in the heart of Ukrainian Village. Featuring a jet tub in the master bath, front patio with hammock, back porch with gas grill, and rare gated private parking for 2 cars. Sleeps 7 comfortably. Steps from Wicker Park, Bucktown, West Town & Downtown Chicago. The entire home is yours — no shared spaces, no surprises. Perfect for families, groups, and extended stays.

Level ◆ Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.

The Velvet Manor | Luxe 3BR • Jacuzzi • Garage

Welcome to The Velvet Manor, a moody, designer-curated 3-bedroom retreat in the heart of Andersonville. Unwind in richly layered interiors featuring a king primary bedroom, two queen bedrooms, dramatic living and dining spaces, and thoughtful boutique-hotel touches throughout. Enjoy one private garage parking space, free street parking, and room for up to 8 guests with two twin rollaway beds available upon request.

Chicago Oasis | Spa Bath, Patio & Fireplace

Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Space to live, space to play, space to call home. Our spectacular Two Bedroom Suites boast 1,080 – 1,170 sq ft of modern living space and feature a fully-equipped kitchen, open concept living and dining area, two spa-inspired bathrooms, bedrooms with king beds and an open-air balcony. All suites also feature in-suite laundry, premium appliances, flat-screen TV, complimentary WiFi and local calling.