House holiday rentals in Downtown 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.

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.

NEW! 3BR/2.5B Duplex in Noble Sq

Welcome to our stunning 3 bedroom, 2.5 bath duplexed condo with free parking and ample outdoor space in the heart of the vibrant Noble Square neighborhood. This open, bright and spacious unit is a true urban oasis that will make you feel right at home in the epicenter of Chicago. Our condo is close to some of the city's best restaurants, cafes, and bars, as well as several beautiful parks. With its unbeatable location, modern design, luxurious amenities, and SuperHost service - look no further!

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

Large, Reno’d 3 BR apt near Everything!

This 1700 sq ft 1st floor apt is gorgeous and close to everything in East Lake View. Walk to Wrigley, the El, the lake and pubs, movies, groceries. Walk into the apt entry and into the large LR, facing south w/ great light. Three BRs and 2 BAs are off the hall which opens to a reno’d great room/kitchen/dining area. Plenty of room to spread out; maybe enjoy the 70” tv. King, queen & full beds await. Front porch for am coffee and a deck on the garage for a BBQ. Enjoy! We’re glad to have you!

Cozy Bungalow Steps to Wrigley - Parking Included!

Welcome to your Wrigleyville home-away-from-home, a space that’s equal parts cozy and modern! Whether you’re here for a Cubs game or concert at Wrigley, a family getaway, or a weekend exploring the city, this home gives you the perfect blend of convenience, style, and true local charm! 🏡 Features • A spacious main living area • Comfortable, hotel-quality bedding • A fully equipped kitchen • Clean bathrooms with essentials • Smart TVs & fast WiFi • Free onsite parking for 2 cars

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 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. The property has a parking slab in back which 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 you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

ALOHA Tropical Penthouse in Wicker Park Sleeps 14

Follow @bangtel for perks and deals! Look no further for your vibrant city escape! Welcome to your tropical penthouse paradise, ALOHA — a 2,000 sq ft oasis in the ❤️ of Wicker Park. This modern, design-forward retreat blends Hawaiian vibes with bold color, playful energy, and luxurious comfort. Just steps away, discover Wicker Park’s best restaurants, boutiques, nightlife, and parks — the ultimate blend of urban excitement and laid-back luxury.

Peaceful Modern Full House in Trendy Bridgeport

Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today!