Holiday houses in 31st Street Harbor

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Top-rated holiday rentals in 31st Street Harbor

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Guest favourite

A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.

Apartment in Chicago

4.96 out of 5 average rating, 70 reviews

Sunny Penthouse - Oakwood Beach

Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

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Top Guest favourite

A living area features a dark blue sofa facing a glass coffee table, positioned on a patterned rug. Light blue curtains frame a window, while a small round table sits next to a potted plant. A wall decor piece with a Chicago flag design is displayed.

Apartment in Chicago

4.94 out of 5 average rating, 32 reviews

La Casita Norte

Modern Bronzeville 1-Bedroom Apartment in quiet, centrally located neighborhood near McCormick Place, Wintrust Arena, White Sox Park, Illinois Tech, and 31st Street Beach. Short ride to Obama Center. Sleeps 4 with a full bed and queen sofa sleeper. Living room, wet bar (w/ fridge, toaster oven, air fryer, Keurig), washer/dryer, dedicated workspaces, and a huge bath w/ separate shower and endless hot water. Well-appointed fitness room includes Bowflex, treadmill, weights, Pilates reformer, mats.

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Guest favourite

A modern living space is illuminated by natural light from large windows, showcasing a stylish dining table accompanied by upholstered chairs. A comfortable seating area features a sectional sofa and decorative accents. A classic game table adds an engaging element to the room's design.

Home in Chicago

4.96 out of 5 average rating, 91 reviews

Oakwood Beach Lake & SkylineViews+CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis in North Kenwood/ McCormick area. New construction with all new finishes and stylish decor. Great natural light, free parking, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of many attractions that the Windy City has to offer. A few minutes from Obama Presidential Center, Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st and Oakwood Beach Perfect for photos and filming!

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Superhost

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Apartment in Chicago

4.81 out of 5 average rating, 1,029 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

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Guest favourite

Apartment in Chicago

4.82 out of 5 average rating, 68 reviews

West Loop Urban Chic Coach House

Welcome to this historic neighborhood in Chicago, a cultural tapestry, rich in history and bursting with energy. Enjoy strolling along the streets lined with historic buildings, savor diverse culinary delights. Bronzeville is not just a place to stay; it is a community experience Enjoy, this one-bedroom, full bathroom historic coach house with a full kitchen, smart TV, and dedicated living space. Unwind in comfort with an in-unit washer/dryer. Plenty of street parking available.

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Guest favourite

A modern living area features a navy blue sectional sofa adorned with light throw pillows. A round coffee table holds a woven basket and a vase of vibrant red tulips, adding a touch of color. A piece of artwork hangs on the wall, complementing the neutral decor.

Apartment in Chicago

4.89 out of 5 average rating, 199 reviews

Modern 2BRD apartment| 5min to McCormick Place

Stay in a newly remodeled, spacious 2-bedroom apartment in Chicago. FREE STREET PARKING (a rare gem in Chicago!) Just blocks from Illinois Institute of Tech, a 7-8 min walk to Green/Red lines, 15 min walk to White Sox stadium, 20 min walk to 31st St Beach, and a 5 min drive to McCormick. Sleeps up to 4 with 2 private bedrooms, full kitchen, workspace, TVs & WiFi. Please note: This is a multi-unit building with long-term tenants, so occasional noise from neighbors may be heard.

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Top Guest favourite

A cozy living area features a light-colored sofa adorned with a textured throw and a contemporary black-and-white artwork on the wall. A sleek kitchen island with two bar stools sits adjacent to the living space, illuminated by pendant lighting. Large windows provide a view of the outdoor greenery.

Guest suite in Chicago

4.91 out of 5 average rating, 81 reviews

Comfy suite w/ steam shower near McCormick Place

Welcome to the landmark! Our well appointed studio space is situated in the historic Calumet-Giles-Prairie District; minutes from McCormick Place, Sox Park, Wintrust Arena, IIT, and downtown. Walk to 31st St Beach, bike to Museum Campus. Perfect for business or leisure; enjoy steam shower, Wi-Fi, smart TV, and full kitchen. Easy access to major highways and public transit. We also offer a Honda Accord rental car on Turo for your convenience upon inquiry.

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Guest favourite

A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.

Apartment in Chicago

4.95 out of 5 average rating, 127 reviews

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

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Superhost

Apartment in Chicago

4.83 out of 5 average rating, 164 reviews

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

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Superhost

A cozy seating area is depicted, featuring a blue couch adorned with a Chicago Blackhawks blanket and decorative pillows. A small coffee table is placed on a red patterned rug, accompanied by a light gray armchair. Natural light enters through a window, enhancing the inviting space.

Apartment in Chicago

4.89 out of 5 average rating, 132 reviews

Chicago Themed Garden Unit - Historic Bronzeville

Get the Ultimate Chicago Experience in this Beautiful, Newly renovated Private Apartment. This private unit has everything you need for a if you want to stay in and cook your own meal or get out and explore the town! We are Conveniently located only 10 minutes from the center of Downtown Chicago and also has a number of additional activities within walking distance. Great for a quick or a long stay in the Windy City!

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Guest favourite

Apartment in Chicago

5 out of 5 average rating, 26 reviews

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

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Guest favourite

A modern living area is highlighted by a large, light-colored sectional sofa adorned with a dark throw blanket. A uniquely shaped wooden coffee table rests at the center, complemented by a textured, dark area rug. A decorative wall art piece enhances the backdrop.

Condo in Chicago

4.95 out of 5 average rating, 87 reviews

The Modern Woodlawn 2 Bed 2 Bath

Enjoy a stylish experience at this centrally-located place. Minutes from University of Chicago, the upcoming Obama Presidential Library, Golfing at the South Shore Country Club, Lake Michigan, Public Transportation and Downtown Chicago. There is an ALDI grocery store around the corner. Jewels Grocery Store is a few minutes drive by car. Free Street Parking.

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