Holiday rentals in West Side

Beautiful Chicago Greystone

Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

Cozy Spacious Condo Sleeps 6

Our welcoming second-floor apartment offers a relaxing updated space to call home during your stay in Chicago. We designed the space to be a home away from home. The apartment's 2 bedrooms and spacious daybed, that converts to a king bed, will ensure you are well-rested and recharged so that you can fully enjoy our wonderful city. Whether you are in town for work or for pleasure our condo will make your stay a great one! We deliver as SUPERHOSTS. We ask that you respect all house rules! Thx

Dwntown Mins Away/Relax & Stay! Bus/Train Friendly

Take it easy in this peaceful and cozy sleeper, central to everything Chicago has to offer and only minutes from downtown. Take advantage of all of the amenities while your here and enjoy the city night life with all of the great entertainment and restaurants Chicago has to offer. Newley rehabbed with high end appliances and fixtures that you, your significant other or family can enjoy. This relaxing vibe is one that will make it feel like a home away from home with all that it has to offer.

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.

Beautifully Renovated Loft-Style Coach House

Stay at this beautifully renovated all-brick coach house in lovely Humboldt Park/West Town! Once a cigar factory in 1908, this unique space has been fully rehabbed & restored for a charming and industrial stay. Its an open-concept loft-style house, and is entirely private - no neighbors above or below you. It boasts a balcony and a large rooftop deck with gorgeous city skyline views. We are proud to be a family-owned rental and take care and pride in this special space! Welcome to Chicago!

【Central】- Eclectic Fun 1BR APT in Wicker Park

Located in the heart of Wicker Park! Just a 5-min walk from the CTA blue line Damen station. This bright second floor 1-bedroom, 1-bath apartment allows you to access EVERYTHING Chicago has to offer all within short walking distance, with great nightlife. Just walk downstairs, you will find trendy restaurants, cocktail bars, cozy coffee shops and a variety of shops in this popular neighborhood. Want to explore downtown? Uber/Lyft or Hop on the CTA "L" train to go anywhere in the city.

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

The Bell House: Apartment #1

Charming 2BR Wicker Park apartment blends modern luxury with historical charm. Fully renovated; new appliances, private deck, full kitchen with cookware, & dedicated workspace. Steps from bars, restaurants, and Blue Line for city/airport access. Ideal for both leisure and business travelers seeking a comfortable, convenient Chicago stay. We offer a unique blend of comfort and location in a vibrant neighborhood. Perfect for exploring on foot, but ample street parking as well!

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.

Rooftop Skyline | 5 Ensuites | Games | DT 14 mins

The Monticello ~ Rooftop deck, skyline views, game room, 5 bedrooms w. ensuite bath! ★ "Beautiful, well appointed, and has thoughtful details." ☞ Fully equipped + stocked kitchen ☞ Game room w/ mini ping pong and board games ☞ Dedicated workspace + 1 Gig WiFi ☞ Parking → secured garage (2 cars) ☞ Indoor electric fireplace ☞ Multiple smart TVs (5) ☞ 3 separate bar areas 14 mins → Downtown Chicago 22 mins → Chicago Midway Airport ✈ 25 mins → Chicago O'Hare Airport ✈

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Chicago Row House Garden Apartmt

This stylish urban garden apartment is a comfortable stay just a few blocks from the United Center and 1 mile from the very popular West Loop and Fulton Market areas! Street parking is readily available and free! We are a 3 mile straight shot down to Millennium Park in the Loop. Take the “L”, bike or walk there and hit Greek Town, the Lyric Opera, the Sears (Willis) Tower, the Art Institute and the Bean (Cloud Gate) along the way!