Townhouse holiday rentals in Chicago

Upscale Home in Lincoln Park Minutes from Downtown

Minutes outside downtown Chicago, built in 1890, this gorgeous fully-remodeled modern Victorian-era row house is located in the heart of Chicago’s historic and vibrant Lincoln Park. One of Chicago’s most affluent neighborhoods! > Walkability score of 98/100 > 4 min walk to the train station, steps to bus stops, short Uber ride to all top Chicago attractions > Across DePaul > Amazing parks & bike trails, free zoo, performing arts, shops, nightlife, spas & some of Chicago’s finest restaurants

Heart of the City Group Hub • Patio • Fireplace

Walk to almost everything Chicago has to offer- Downtown, Mag Mile, North Ave beach, Lincoln park zoo, restaurants, bars, boutiques. Bring family or friends to this Haute Couture Designer themed townhouse spanning over two levels on a quiet neighborhood street in historic Old Town. 4 bedrooms, 2.5 baths, patio, parking for 1 car, laundry, fully stocked kitchen with stainless steel appliances & granite countertops. Pets welcome! What else can you possibly need? Message me if you have questions!

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Hidden Gem - 3 Story House & Pet Friendly!

Cozy & entertaining family -pet friendly property in the heart of Chicago - Lincoln Park. This Smart triplex has a fully-equipped kitchen. Large patio w/ sunset views. 3 bedrooms & 2.5 bathrooms. A Foosball table, 82' TV & BAR to enjoy a night in. This property is perfect to book w/ family or friends. Its spacious yet set up the right way to entertain in one floor, cook in another & sleep without having to deal with noise. Pets: Certain restrictions may apply. It is $35/night per pet

Cozy & Bright Townhome near O’hare -Self Check In-

Escape into this Montclare Masterpiece! Be one of the first guests to enjoy our revitalized, fully-stocked home with attached deck. This 3-level home comes with a spacious, light-flooded living area with attached open kitchen w/ SS appliances, granite countertops/ backsplash, and accent lighting - perfect for larger groups. On the third level you'll find 2 elegant bedrooms with ample closet space, updated full bathroom, and in unit washer and dryer provide all the essentials and more!

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS/PERMIT VISITORS. Please agree per message to confirm

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Chic Lincoln Park Townhome | Rooftop + Glam Bar

⭐️ Lincoln Park Luxury | Rooftop + Glam Station | Sleeps 10 ⭐️ Stay in the heart of Lincoln Park, one of Chicago’s most vibrant neighborhoods, where tree-lined streets meet world-class dining, shopping, nightlife, and the lakefront. This beautifully curated 3-story townhome blends luxury, comfort, and style, making it ideal for bachelorette weekends, girls’ trips, family stays, and celebratory group getaways. 📍 Steps from Lincoln Park Zoo, cafés, boutiques & the lakefront

Spacious 4BR, central ChinaTown by McCormick/DWNT

Unique 2 story duplex situated in the heart of Chinatown. It’s beautiful, modern and newly furnished 4bedrm/3baths for business conventions and vacation travel. One FREE private parking and plenty of street parking. This home has 8 beds, 2 sofa beds can accommodate 16 or more guests. Walking distance to Ping Tom Park for Water Taxi, Public Transportation, Starbucks, McCormick Place Convention Center, Wintrust Arena. Minutes to Downtown and popular attractions.

Wicker Park Crash Pad + 7 Beds

🚀Houston, your group has found its launchpad. 🛸This funky, space-themed 2-level landing pad in the heart of Wicker Park sleeps 8 guests across 7 beds, with 2 bathrooms, arcade games, and 420-friendly outer space vibes. Enjoy the main-floor living room and kitchen, with bedrooms in the underground bunker below. Incredible central location in Chicago. Book it before someone else does.

Cheerful 3 story townhouse Old Town/LP

Discover a luxurious three-story townhouse, ideally located for exploring Chicago's Lincoln Park Zoo, Lake Michigan, Magnificent Mile, Old Town, and Lincoln Park's vibrant dining and shopping. Enjoy a complimentary designated parking spot. Please note: due to a host's medical condition, we cannot accommodate service animals that are cats or dogs. A fee applies for more than two guests.