Carl Sandburg famously called it “City of the Big Shoulders,” but there are plenty of big houses, too, from the stately mansions of the Gold Coast to expansive hipster homes on the Near West Side and sprawling suburban properties. Get a big group together, and your party or family can combine luxury living with affordability. Here are a few that struck our eyes.
Prices and availability are subject to change.
Related: 30 Jaw-Dropping Yet Affordable Mansions for Rent Across the Country
The Wolcott
Wicker Park | Sleeps 16 Book It
This home in lively Wicker Park makes a striking presence on its corner lot with a three-story brick and glass facade. The back courtyard mixes grass with slate tiles and is marked by the painted mural on the brick building next door. Rooftop decks include a basketball hoop and a hot tub for a truly luxurious stay. While in the neighborhood, you can visit Wicker Park’s clubs, bars, and funky boutiques.
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The home includes six bedrooms and six bathrooms, a workout room, wine cellar, game room, and pool table. Furnishings are modern yet comfortable. Don’t miss the skyline view from that rooftop lounge. There are multiple living rooms with TVs, as well as a private parking garage.
The Orleans
Near North Side | Sleeps 16 Book It
This historic, storefront brownstone includes four separate suites, each with its own kitchen. The group can gather on the rooftop patio, with a clear view of the John Hancock Center. There are bike rentals just outside the front door, and easy access to the El, as well as River North’s galleries and Lincoln Park.
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Throughout the building, rooms are warmed by exposed brick and brightened by modern art. Exposed ductwork adds to the industrial-chic appeal. Day and night views from the roof are Chicago at its best.
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Best Reviews
Noble Square | Sleeps 12 Book It
With more than 40 reviews, this five-bedroom, five-bath home has a five-star rating, recommending it as “perfect for a family reunion.” Its neighborhood is a dining destination, and the surrounding neighborhood is full of hot bars, cafes, and boutiques. Outside, the 1890s brick calls to mind the character and warmth of classic Chicago neighborhoods, as does the adjacent park.
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On the inside, renters will enjoy a chef’s kitchen with a SubZero refrigerator and Wolf stove. Each level of the home has a deck, and one bedroom has a fireplace. The interior is elegant but cozy, with new furniture and wood floors. A basement den includes a wet bar with a microwave and full-size refrigerator.
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Double Penthouses
Fulton Market | Sleeps 24 Book It
Historically a warehouse district (and site of the 1886 Haymarket Riot), today’s Fulton Market has been thoroughly gentrified into a destination for dining, shopping, and nightlife, as well as the city’s Google headquarters. Two side-by-side penthouses occupy the top floor of this 1920s building; the rental, which includes both penthouses, has six bedrooms and four baths.
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A brick-and-timber warehouse has been converted into the lofts that house these rentals. Bedrooms have partial walls, while living rooms are on an open plan with industrial-chic decor. There are plenty of bunk beds suited toward child-friendly rooms or very close friends. Outside your door: dining courtyards, patios, and live music venues.
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Four Floors, Four Decks
Lakeview | Sleeps 17 Book It
On the western edge of Lakeview, this single-family home can sleep your group of up to 17. You’ll be a short drive from Wrigley Field and Lake Michigan. Floor-to-ceiling windows fill the home with light, and the uppermost of four decks takes in sweeping views of downtown Chicago.
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Inside the brick building are multiple living rooms, several big-screen TVs, and an entirely wood-finish kitchen. The backyard includes a patio with a firepit. Get there early and claim for yourself the main bedroom with its fireplace and recessed TV.
Related: The Best Lakefront Vacation Rentals Across America for a Peaceful Getaway
Suburban Spread
Northbrook | Sleeps 20 Book It
Need to be on the North Shore? This 6,000-square-foot mansion has enough entertainment options to keep you from splurging at nearby Northbrook Center. The enormous living room has a two-story bay window. An upstairs bedroom features a steam shower, and two bedrooms offer spa tubs. The massive backyard includes a fireplace, hot tub, trampoline, and jungle gym with a climbing wall for kids.
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In addition to plenty of areas to sit and sleep, the home is filled with entertainment options. Those who are motivated can use the fully equipped gym. The downstairs game room contains air hockey, a pool, and ping pong. Bring some popcorn down to the home theater, which has recliner seating for eight.
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Joyful Home
Lincoln Park | Sleeps 14 Book It
There’s nothing cheap about this contemporary home, but there’s nothing ordinary about it, either. The open-plan kitchen gets its light from a wall of windows that retract to create indoor-outdoor space with the patio and its gas fire table. There is even a basketball half-court outside. Venture farther from home, and you’ll find Lincoln Park, the zoo, Lake Michigan, and the neighborhood’s tony shops just blocks away.
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Warm brick and wood are enlivened by bright colors throughout the decor, and multiple murals and large-scale art. The primary bedroom has an infrared sauna. Downstairs, gather in the home theater. Throughout the home, sectional sofas and lounging furniture are made for long, lazy chats.
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Indie Style
Logan Square | Sleeps 16 Book It
Logan Square has been one of Chicago’s destinations for music and art since the 1990s, and this home provides access to it all, with both privacy and peace in the main house, guest house, and in the backyard that joins them. As you stroll N. Milwaukee Blvd., you’ll find both upscale dining and the area’s longtime Latino establishments. Don’t miss The 606, the elevated park that’s Chicago’s answer to New York’s High Line.
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Fourteen-foot windows on the first floor fill the space with light. The open plan features a solid-wood dining table, a stylish contemporary living room, and a modern kitchen with an island for extra seating.
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Brick and Steel
Bridgeport | Sleeps 16 Book It
You won’t be in the middle of the action in this contemporary Bridgeport home, but the savings are noteworthy, and you’ll be staying just steps from an El station. White Sox fans, however, are just minutes from the action, and both Greek Town and Chinatown are a short drive away. With 6,200 square feet, you’ll have plenty of space as well.
Related: Coolest Vacation Rentals Near Your Favorite Baseball Stadium
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The home was designed for large groups, with air hockey, foosball, and a pool table. Eight bedrooms and five bathrooms promise plenty of space for everyone. The deck and backyard aren’t overly furnished, but they are both large.
