8 Cool Places to Rent on Your Next Trip to Chicago

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By Michele Koh Morollo
With its iconic skyscrapers such as the neo-Gothic Tribune Tower, the Art Deco Carbide & Carbon Building, and modern structures like the Sears Tower, Chicago is certainly one of America’s most architecturally interesting destinations.

When it comes to home interiors, Chicago residents are known for keeping the design subtle yet sophisticated with subdued color schemes and industrial and midcentury details. 

Whether it's for work, vacation, or visiting family, experience the Windy City in style at one of these vacation rentals that range from $90 to $274 per night. And don't forget to pack a big coat!

1) Four-Bedroom Apartment in Lincoln Park

Average price: $211 per night

Just a short distance from the Fullerton transit station, this four-bedroom apartment, which comfortably sleep up to eight guests, has warm wooden floors, a large living room, plenty of light-filled spaces, and a gray, green, and pink color scheme. Book Now

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2) Two-Bedroom Apartment Near Restaurant Row

Average price: $128 per night

Located near Chicago’s "Restaurant Row," this sleek two-bedroom apartment with a balcony pays homage to its neighborhood’s industrial heritage with dark wood and Bauhaus-style furniture. Book Now

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3) Jefferson Park Apartment

Average price: $90 per night 

Situated just 15 minutes from downtown Chicago in the Jefferson Park neighborhood, this two-bedroom apartment with high ceilings has four additional portable twin beds, allowing it to fit up to eight guests. Book Now

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4) Three-Bedroom Apartment in Lincoln Park

Average price: $145 per night 

This 1,175-square-foot, three-bedroom apartment is furnished with a neutral color palette and has floor-to-ceiling windows that bring in lots of natural light. Book Now

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5) South Loop One-Bedroom Apartment With Rooftop

Average price: $132 per night

Perfect for couples or solo travelers, this one-bedroom apartment in the vibrant South Loop neighborhood has a kitchen that's fitted with Florense cabinets, stainless-steel appliances, full-height windows, and a rooftop deck that presents beautiful city views. Book Now 

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6) Penthouse Suite in Downtown

Average price: $274 per night

An easy five-minute walk from many of the city’s finest shops and restaurants, this penthouse suite includes a large private roof deck, three bedrooms with seven queen-size beds, two bathrooms, and a fully equipped kitchen. It's ideal for large groups. Book Now

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7) Scandinavian-Inspired Lincoln Park Apartment

Price upon request

This four-bedroom apartment in the colorful lakeside neighborhood of Lincoln Park is decked out in warm wood and furnished with cozy, Scandinavian-style furnishings and fabrics. Book Now     

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8) North Hudson Condo Apartment

Average price: $156 per night

Located where the Chicago River meets Lake Michigan, this two-bedroom, 42-floor apartment in the Optima Center condominium building offers beautiful views of Magnificent Mile and is close to the beach. Guests who rent the apartment will also have access to the condo’s pool, fitness center, spa, rooftop garden, and lounge. Book Now  

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