House holiday rentals in West Loop, Chicago

4.87 out of 5 average rating, 128 reviews

Home in Lake View

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

4.92 out of 5 average rating, 269 reviews

Home in Wicker Park

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

4.92 out of 5 average rating, 24 reviews

Home in Elmhurst

Premier 5BR/3BA Modern Retreat with King Suite!

Beautiful 5BR/3BA Retreat in a Chicagoland suburb! ☆ Newly renovated and stylish, this spacious home features a modern open layout, luxurious bedrooms, a gourmet kitchen, and elegant bathrooms. Explore the vibrant Chicagoland neighborhood with local shops and parks, then come home to relax in peace. Conveniently located in a prime area, a quick drive from the airport or Oak Brook shopping mall. Ideal for families, groups, or anyone seeking comfort and convenience. Book now for a memorable stay!

4.84 out of 5 average rating, 100 reviews

Home in Logan Square

California Cottage/4br prime location Logan Square

Incredible location in Logan Square! Walking distance from dozens of restaurants, breweries, bars, nightlife, the square, the farmers’ market and much more. Free street parking in front. 2 blocks from 90/94 and close to the blue line train which goes to many of Chicago’s iconic neighborhoods, downtown, and directly to O’ Hare airport. Beautiful house with high ceilings on the 1st floor. Lovely kitchen with nice appliances. 2 cozy bedrooms upstairs. One with a queen and the other has 3 twins.

4.87 out of 5 average rating, 119 reviews

Home in Irving Park

Stunning 6 BR Home * Chicago * Centrally Located

Welcome to a newly built luxury 6 bedroom house in Chicago’s family friendly Albany park neighborhood. Centrally located - close to downtown (25 min), Wrigley Field (15 min) and O'Hare (15 min) Large common areas and a chefs kitchen with a 5 person island allows large parties and families to stay comfortably. The house offers spacious rooms and a full laundry room on the second level. The home also includes a 2 car garage and the convenience of not having to worry about parking in Chicago!

4.87 out of 5 average rating, 23 reviews

Home in Elmhurst

Enamored in Elmhurst

Have fun with the whole family at this beautifully renovated house with and open floor plan, fully stocked kitchen, 4 bedrooms, 2 bathrooms with smart tv's in all the bedrooms and quick reliable wifi for all to enjoy. Home is located only minutes from the highways, enjoy the deck right off the living room and overlooking a private yard . House also has a fully finished basement with 2 of the bedrooms, a full bathroom and a theater room with a sectional sleeper sofa if more space is needed.

4.94 out of 5 average rating, 33 reviews

Home in Old Town

Downtown Gem *Patio *Parking *Huge

Walk to everything Chicago has to offer- Downtown and Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars, boutiques of Old Town and Gold Coast, bring family or friends to this spacious house on a quiet neighborhood street in historic Old Town. This amazing home has 6 bedrooms, 6.5 baths, 3 outdoor areas, 2 stunning kitchens and a bar, 2 washers & dryers, 2 car garage. It is expandable from small family to large group. Pets are welcome! Message me if you have questions!

5 out of 5 average rating, 11 reviews

Home in Avondale

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

4.96 out of 5 average rating, 110 reviews

Home in Elmhurst

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

4.85 out of 5 average rating, 101 reviews

Home in Des Plaines

Cozy Home by O'Hare + EV Plug

Family-friendly 3BR/2BA home in Des Plaines! Enjoy arcade games, board games, and an EV charger. Nestled in a quiet neighborhood near parks, shopping, and entertainment. Just minutes from Des Plaines Theatre, Rivers Casino, Mystic Waters, and Fashion Outlets of Chicago. Ideal for families or groups seeking comfort, fun, and convenience with easy access to top attractions and O'Hare Airport. Your perfect home base for exploring the Chicago area!

4.95 out of 5 average rating, 184 reviews

Home in Lake View

Wrigleyville Greystone

First floor guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line station. Open floor plan with full kitchen, DR, double LR with 55” TV & foosball table, 3 bedrooms with queen size beds, 2 full bathrooms with bidet toilet, exercise room & back patio with sofas, table & koi pond. Since we live here and have another guests house in the building, we do not allow parties or large groups.