Lake house holiday rentals in Chicago

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.

Amazing Location! Spacious Duplex Getaway

Welcome to your perfect getaway! This beautifully renovated duplex is ideally located, just steps away from charming coffee shops, local restaurants, and Lake Michigan. Only 2 blocks from Metra and CTA stops, you will have convenient access to downtown Chicago, Wrigley Field, Northwestern University and much more. With a free off-street parking spot, comfortable king-sized beds and fast wi-fi, whether you're here to explore or just relax, you'll love the convenience and comfort this home offers.

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

*New* Luxury Wrigley Penthouse, Free Parking

✨ NEW Guest Favorite in Chicago Wrigleyville! SPACIOUS 3BR, 2.5BA DUPLEX, UP TO 12 GUESTS w/ NEW FURNITURE, BEDS & GAME ROOM ✨ A standout stay in Chicago — nothing else like it! Just a 5-min walk to Chicago Red Line Station (10 mins to Downtown Chicago!) & only 5 mins to Wrigley Field. Walk to cafes, shops, parks & more. Includes FREE parking, fast Wi-Fi, foosball & arcade games. Perfect for friend groups, families, corporate housing, and digital nomads! A perfect score in the heart of Chicago!

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Bronzeville 42: Art & Hospitality Mins to Downtown

Bronzville 42 (B42) is a vibrant space where art meets hospitality! Featuring captivating artwork from the owner's collection, B42 is beautifully decorated and conveniently located just 12 minutes from Downtown and minutes to Hyde Park, the lakefront beach, and the upcoming Obama Presidential Center (opening spring 2026). Dining: - Table seats 6 - Kitchen seats 4 Accommodations: - Sleeps 8 Bedrooms: 1. BR1: King bed 2. BR2: 2 Twin beds 3. BR3: 2 Queen beds Bathrooms: 2 Full Bathrooms

Ideal Group Getaway: Best Location, Parking, Patio

Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Within walking distance of Downtown, the Magnificent Mile, restaurants, bars, boutiques, Lincoln Park, and beach. Enjoy an open floor plan with a spacious living, dining, and sitting area with a cozy fireplace. The home offers 3 bedrooms, 2.5 baths, a fully stocked kitchen, 2-car garage, backyard, and laundry. Pets are welcome! Perfect for a relaxing city escape. Message me with any questions!

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home with a separated basement apartment nestled in the historic Bronzeville neighborhood. This beautiful residence boasts enchanting décor and well-appointed living spaces that promise a memorable stay. Its minimalist charm and comfortable setup reflect a contemporary/modern aesthetic, making it an irresistible choice for guest. Just 6 mints from the downtown, 20 mints from Midway Airport, and 4 mints from McCormick Place & UOC.

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Luxurious Gold Coast Townhome – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this stunning 4,000 sqft Gold Coast residence. Perfect for groups of up to 12, this home features 4 spacious bedrooms, 4.5 bathrooms, and a ceiling-length window with incredible views. Enjoy a variety of indoor games and make use of the convenient rooftop. Whether you're here for leisure or work, this property offers modern amenities and unforgettable comfort in the heart of City

Hot Tub Logan Family Designer Home

Enjoy a beautiful family home on a quiet tree-lined street designed by one of NYC's top designers -- with abundant art, lots of space for kids, and a hot tub! Freshly redesigned and between Wicker Park and Logan Square, this is a perfect location for family and just a few minutes from downtown Chicago. Luxury linens, bedding, and touches abound. Explore the elevated 606 trail, excellent restaurants within walking distance, and a work desk, 4K monitor, and playroom. And secret beach!

Spacious Two Story Luxurious Home w/Outdoor Deck!

Our home is in a quiet neighborhood, on a corner with abundant space and natural light. There are two spacious levels with two bedrooms upstairs and one downstairs. The large outdoor brand new deck was designed for barbecuing, star-gazing or just relaxing. Beautifully polished wood floors with a modern kitchen make this home ideal. A claw foot soaking tub is perfect for the end of a day and truly ensures a relaxing stay and a deep, refreshing sleep. Free parking!

Sleepy sanctuary

A spacious, modern and comfortable 2 bedroom, 1 bathroom flat situated in the quiet and relaxing Evanston neighborhood, Kingsley. This corner property comfortably sleeps up to 6 so whether you and your sweetheart need a change of scenery or the family wants a getaway spot close to Lake Michigan beaches, we can accommodate a variety of guest sizes. Includes a laundry room, garage parking for one vehicle, two work spaces with monitors, and large backyard.