Apartment holiday rentals in West Loop

Welcome to the Chi! Close to Downtown

Welcome to this contemporary, urban retreat in the bustling heart of River West. This entire unit is thoughtfully designed with modern convenience, catering to those seeking stylish and comfortable accommodation. This trendy unit is in a prime location, just a short walk to the Blue Line and minutes away from 90/94. With an array of restaurants, grocery markets, coffee shops, and stores within walking distance, you'll have the best of Chicago at your doorstep. 5 minute drive to United Center.

Bold Ukrainian Village 2 Bedroom w/Garage Parking

Our bright Ukrainian Village apartment is on a quiet, tree-lined street, but near some of the most exciting restaurants, bars, and vintage shops in the city, and only a mile north of the United Center - it's the best of all worlds! The layout is equally ideal for friends traveling together as it is families, as well as work from home life. We've got a backyard and patio for you to share, we're walking distance to Wicker Park, and close to plenty of CTA options that'll get you down to the Loop.

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

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.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

The Penthouse Gallery at OHC

Welcome to Open House Contemporary, Chicago's best Airbnb! Featured in Architectural Digest (Aug. 2018) and as one of Bobby Berk's (Queer Eye's designer extraordinaire) top 10 AirBnbs in CN Traveler (Sept. 2018). Come live alongside Open House Contemporary’s latest exhibition from some of America's finest emerging artists. Enjoy lots of natural light from this Penthouse condo through walls of windows or slide open the balcony doors for a relaxed evening at home.

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.

Great group stay - 10 adults 4 bdrm w workout area

Duplex down of building that sleeps 10 adults 2 children on rollaways*, 3 bathrooms, 2 king bedrooms and 2 queen bedrooms and 1 additional queen bed in the open basement family room tucked away in the corner, bring the entire family or friends for time in Chicago, we now have added a Peleton and a Concept 2 rower. * if you need the 2 rollaways you’ll need to let me know 24 hours before checkin.

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Location, Location... Food/Entertainment to the max! Just renovated apt. situated above and hosted by Steingold’s of Chicago (yes, bagels are included), the Midwest’s most lauded deli. Next-door to iconic Music Box Cinema. An 8 minute walk to Wrigley Field and all of its amazing neighbors. Right in the middle of Southport Corridor, Chicago’s hottest neighborhood shopping district.