Calendars have been consulted, dates have been selected, and now you’re ready to plan an ultimate family get-together to usurp all others. The main objective: spend quality time together under one roof or in one building. Fortunately, booking a vacation rental has never been easier—possibilities abound. Whether your immediate and extended family is massive or more manageable in size, we’ve got you covered. Keep reading to discover our favorite Chicago Airbnbs that are perfect for you and your loved ones.
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Stunning & Spacious in Lincoln Park
After a long year apart (or even together), this rental is the ideal location to get together with everyone in your family, under one roof. With four bedrooms and 2.5 baths, you’ll have plenty of space to spread out. Play pool, ping pong, or Foosball in the expansive game room. Let the kids challenge each other on the Xbox. Read books from the in-house library and create music on the piano. Gather around the dining room table each night and enjoy a meal together,
Five Bedroom Home with Room to Spread in Trendy Chicago Neighborhood
Sometimes a big ole house is just what you need to accommodate everyone in your family. With a private rooftop deck, hot tub, and 75” television, you'll never want to leave this doozy. Plus, this home has multiple rooms with different set-ups, including bunk beds and cribs for the kids.
The Neighborhood Hotel in Lincoln Park
Stylish and design-forward, this little gem is a sweet treat full of eye candy. Book as many rooms as you need—The Neighborhood Hotel has 14 large suites and a coach house, complete with a full kitchen, washer and dryer, Sonos speaker system, and thoughtful artistic touches like pops of pink paint, table-side plants, and fun artworks. Think of it as an apartment beautifully masquerading as a hotel room.
Stunning Old Town Penthouse with Private Rooftop
If a 4,000 square foot luxury penthouse, in the heart of downtown, sparks your interest, then look no further than this rental. Built in 1897, and renovated in 2017, this is a treasure like no other. There are two units connected in this penthouse, linked by a private staircase, allowing for two living rooms, two kitchens, and two laundry rooms.
Lakeview Greystone One Block from Wrigley Field
Cubs fans will delight in this rental, located just one block from the famous Wrigley Field. This Greystone home is impeccably furnished, with everything your family might need. Play ping pong in the recreation room, enjoy drinks on the front stoop or back porch, and relax in front of the television after exploring the neighborhood.
Bright, Modern Studio in the Heart of Logan Square
Contemporary and light-filled, this well-located cozy rental has charming touches like a record player, potted plants, and spice racks in the fully stocked kitchen. There’s a formal dining area and a workspace with high-speed WIFI. You’ll be within walking distance to all that Logan Square has to offer in the way of restaurants, bars, and boutique shops.
Feel at Home in Chicago, Steps from Evanston
Rent this entire vacation home, suitable for five guests, which has two bedrooms and one bathroom. This urban condo has a funky vibe with metal art and brightly colored rooms. A parking spot and private entrance will make you feel like a local, giving you ease of travel.
Eclectic & Colorful Retro Apartment near Logan Square
With a yellow carpet, red couch, and multi-hued curtains throughout, you’ll find many backdrops for snapping Instagram photos. You’ll be within walking distance to nightlife and urban exploring, as well as public transportation.
Come Together in Vibrant Restored Mansion near Wrigley
Located in one of Chicago’s most popular neighborhoods, this Airbnb is a true gem. With a whopping nine bedrooms, it’s easy to gather here with your whole family. Enjoy a cup of coffee in the backyard, play a round of pool, or gather around the dining room table and play a board game. This rental, full of art and pops of color, has everything you might need for your multigenerational family vacation.
Coach House Apartment, Little Italy
An office, a fully stocked kitchen, and a full living room media center make this rental ideal for those who seek the creature comforts of home. Two bedrooms, a washer and dryer, and beautiful curb appeal complete the picture at this Little Italy Chicago home.
Relax with Family in a Luxury Chicago Single Family Home
This rental is as close to living like a Chicagoan as possible. Spread out over four levels throughout 4,500 square feet of space in this five-bedroom relaxing home. There’s a comfortable family room in the basement, common spaces, a laundry room, and an outdoor deck.
East Village Flat
For a four-bedroom and four-bathroom home, this East Village rental is quite affordable. Clean and comfortable, this townhouse has a fully stocked kitchen, fireplace, outside deck, and skyline views. And, if you’re bringing along your pet, you’ll find that the accommodations are restful for Fido as well.
River West 4-Bedroom with Incredible Renovation!
The heart of Chicago beats in the neighborhoods as they say. Enjoy this two-level River West home and feel like a real deep dish pizza-eating Chicagoan with a stay here. Ideal for extended families, four bedrooms are spread out over multiple levels, giving visitors privacy and space.
Hyde Park 5 Bed, 3 Full Bath Condo
The first thing you’ll notice in this rental is all the gleaming hardwood floors. Situated five minutes from the University of Chicago and the hospital, this location is perfect for those who want a large and affordable condo, near Lake Michigan and downtown, in Hyde Park.
Magic Factory, Chef kitchen, Art, Dine, Relax
For staycationers that want to stay somewhere really special and unique, look no further than this rental located at the crossroads of Lincoln Park, Old Town, and River North—near public transportation. A former tavern and costume factory, this 3-bedroom open-floor property is complete with a chef’s kitchen and plenty of comfortable places to relax and sit.
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