Vacation rentals in Monroe Harbor

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Top-rated vacation rentals in Monroe Harbor

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Guest favorite

Apartment in Chicago Loop

4.88 out of 5 average rating, 146 reviews

LIVN Millennium Park Downtown Chicago 1 BR

Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly located in the heart of downtown, you'll be steps away from iconic Millennium Park, the vibrant shops of Michigan Avenue, and a world of dining options. This 1 bedroom offers modern comfort with a fully equipped kitchen, including a refrigerator, dishwasher, and coffee maker, plus the convenience of an in-unit washer and dryer, making it ideal for both short getaways and extended stays. Enjo

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Superhost

Apartment in West Town

New place to stay

Luxury Penthouse Collection PH3 - Fulton Market

BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and most luxurious buildings in bustling Fulton Market-the city's center of main nightlife and restaurants. This high-end apartment features onsite management, building gym, common rooftop with amazing city views, 1 bedroom/1 bathroom, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

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Top guest favorite

A modern living room features a warm fireplace with elegant stone detailing. Comfortable seating is provided by a plush sofa alongside a stylish armchair. Natural light enters through multiple windows adorned with blinds. Decorative elements include a wooden coffee table and contemporary wall art.

Apartment in Downtown Chicago

4.98 out of 5 average rating, 164 reviews

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

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Superhost

The spacious bedroom features a large bed dressed in crisp white linens, framed by soft side tables with gold accents. A piece of abstract artwork adorns the wall above the bed, and natural light enters through a large window with unobstructed views.

Apartment in Downtown Chicago

4.74 out of 5 average rating, 1391 reviews

Kasa | Spectacular City Views | 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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Top guest favorite

A modern living area features a comfortable sectional sofa on a vibrant red rug. A minimalist coffee table sits in front of a mounted television, framed by a black shelving unit filled with books. Large windows allow natural light to fill the space, complemented by stylish artwork.

Apartment in Chicago Loop

4.93 out of 5 average rating, 213 reviews

Brilliant 2BR/2BA Loft I SuperHost I Sleep 6

Enjoy Chicago in our modern & spacious 2-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

ValueFamilyDecor

Guest favorite

A spacious living area is highlighted by large windows that provide ample natural light. A contemporary sofa faces a round black table, complemented by a vibrant red area rug. A striking mural adorns the wall behind the seating, adding a bold artistic touch to the space.

Apartment in Chicago Loop

4.89 out of 5 average rating, 304 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

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Guest favorite

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 West Side

4.95 out of 5 average rating, 131 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.

LocationFamilyPool

Top guest favorite

A light-filled living area features large windows offering views of the city. A stylish sofa and armchair provide comfortable seating, complemented by a round coffee table. A dining table with modern chairs is positioned nearby, surrounded by greenery from potted plants.

Apartment in Chicago Loop

4.85 out of 5 average rating, 154 reviews

Splendid Corner 3BR in the Loop | City Views

Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fabulous city views in multiple directions. This dramatic light-filled three bedroom, two bathroom space is perfect for groups looking for a luxurious escape in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!

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Guest favorite

A modern rooftop deck is presented, featuring contemporary seating with vibrant orange cushions arranged around a firepit. Panoramic views of the Chicago skyline are visible, showcasing a mix of architectural styles under a clear blue sky.

Apartment in Downtown Chicago

4.92 out of 5 average rating, 186 reviews

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

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Guest favorite

Apartment in Chicago Loop

4.87 out of 5 average rating, 61 reviews

Loop 2BR w/City Views | Walk to Millennium Park

Bright 2BR with beautiful city skyline views in historic downtown building. Sleeps 7 with king bed, queen bed, sofa bed, and air mattress. Includes 2 bathrooms, full kitchen, washer/dryer, and WiFi. Walk to Millennium Park (10min), Riverwalk (5min), Art Institute (8min). Building amenities include 24-hour concierge, gym, business center. "L" train just 1 block away.

LocationFamilyLayout

Superhost

A five-story building characterized by its vintage brick facade and decorative ironwork. An outdoor fire escape extends along the side, while large glass windows offer views of the bustling street below. A prominent sign displays the name 'South Loop Club.'

Apartment in Chicago Loop

4.79 out of 5 average rating, 135 reviews

South Loop Studio Hotel (305)

Stay in the center of the action in this one-of-a-kind place! You’ll be within walking distance of Chicago's most iconic landmarks. ⚠️ Please Note: Our elevator is currently undergoing repairs. All guests will need to use the stairs to access the unit. We apologize for the inconvenience and appreciate your understanding as we maintain our unique space!

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Guest favorite