Vacation rentals in Monroe Harbor

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Top-rated vacation rentals in Monroe Harbor

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Guest favorite

A comfortable living area features a dark sectional sofa positioned around a round coffee table. A wall-mounted television is displayed above a modern electric fireplace. Natural light enters through a small window, while a plant and a workspace are subtly included in the room.

Guesthouse in Chicago

5 out of 5 average rating, 7 reviews

Garden Retreat in Historic Bronzeville

Welcome to your home away from home in historic Bronzeville! This private basement unit sleeps 3 with one queen bed and a fold-out couch. Enjoy a full bathroom, private entrance, and everything you need for a comfortable stay. Located near McCormick Place, Chinatown, museums, the lakefront, public transit, and just minutes from downtown. Whether you're here for work or relaxation, we'd be happy to host you! Washer & dryer No chores No dishwasher Early check-in, late check-out if available

The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.

Apartment in Chicago

4.8 out of 5 average rating, 304 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Top guest favorite

Private room in Chicago

5 out of 5 average rating, 127 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

A modern kitchen area features sleek white cabinetry and stainless-steel appliances, including a refrigerator and coffee maker. A comfortable blue sofa is paired with a light wood coffee table. Large windows allow natural light to brighten the space, highlighting the neutral color palette.

Apartment in Chicago

4.54 out of 5 average rating, 59 reviews

Sonder The Plymouth | One-Bedroom Apartment

With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Through the glass doors and chic lobby, gold and wooden accents decorate the open space. You can lounge on the rooftop and savor the city skyline, or bring food to cook on the grill. In your apartment, expansive windows illuminate the open floorplan. Settle into your stay and take advantage of the fully equipped kitchen, in-suite laundry, and cable television. Get in on the Windy City action at The Plymouth.

A modern kitchen is featured with white cabinetry and stainless steel appliances. An island with bar seating is centered, enhancing the open layout. A cozy living area is visible with a dark sofa and a coffee table topped with books. A mounted TV is positioned on the wall.

Apartment in Chicago

4.88 out of 5 average rating, 8 reviews

The Luxe Haven | 1BR | Near City | Free Parking

Keep it simple, Just a few blocks away from Downtown Chicago, The Loop, and popular attractions, this property is the ideal spot for your stay! Carefully designed and fully furnished, the unit offers excellent amenities for both comfort and entertainment: Fully equipped kitchen In-unit laundry Roku TV in the bedroom (bring your own Netflix/Hulu login) Fast WiFi Perfect for healthcare workers, corporate employees, and all travelers seeking a convenient and cozy place to call home!

Superhost

A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.

Apartment in Chicago

4.84 out of 5 average rating, 295 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Superhost

An indoor pool area is framed by tall windows, allowing natural light to fill the space. Elegant seating arrangements are situated around the pool, complemented by lush vertical greenery hanging from above. Soft lighting creates a serene environment for relaxation.

Apartment in Chicago

4.63 out of 5 average rating, 51 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

Experience a lifestyle where everything you need is right at your fingertips in the vibrant heart of Downtown Chicago. Explore the area effortlessly: ✔ Breathtaking views of Lake Michigan and the Chicago skyline ✔ Close to major business hubs and the Loop District ✔ Enjoy a walk along the scenic Lakefront Trail ✔ A lively array of world-class museums, gourmet restaurants, and iconic architecture ✔ Quick access to Millennium Park, the Art Institute of Chicago, and Grant Park

Top guest favorite

Private room in Chicago

4.98 out of 5 average rating, 105 reviews

Private room(s) at a great home in Little Italy .

For single Guests: You will enjoy a nice cozy room with its own private bathroom) in a beautiful home . For two people traveling together There is an additional room adjacent to that room, which is offered for an additional fee. The bathroom will be shared among the two travelers. The house is in Little Italy, conveniently close to downtown, the West Loop, UIC, Rush and Cook County . Only 12-minute away to the CTA Blue line. A stop for Bus #7 is half a block away.

Superhost

A bright living area features large windows that fill the space with natural light, overlooking the city skyline. A blue sectional sofa and a blue accent chair complement the colorful area rug, while a glass coffee table sits at the center, adding a modern touch.

Apartment in Chicago

4.85 out of 5 average rating, 54 reviews

Spacious 2BR Group Stay near McCormick & Wintrust

Welcome and Experience Chicago in style at our modern, luxury 2-bedroom, 2-bathroom suite located on iconic Michigan Avenue in the heart of the South Loop! Just steps from McCormick Place, our spacious 1,200+ sq ft suite is perfect for groups, business travelers, and families. This stylish apartment offers breathtaking skyline views, modern furnishings, and high ceilings that add a bright and spacious feel to every room. With sleeping arrangements for up to 8 guests.

Guest favorite

A spacious bedroom features a king bed with a memory foam mattress centered against a decorative wall panel. Two potted plants add greenery to the room, with modern pendant lights providing illumination. Large windows allow natural light to fill the space, complemented by a comfortable chair and a mirrored wardrobe.

Apartment in Chicago

4.89 out of 5 average rating, 173 reviews

Lovely 1-bedroom serviced apartment near Museums!

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!

Superhost

Private room in Chicago

4.82 out of 5 average rating, 203 reviews

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

Guest favorite

A private room features a spacious bed with crisp white bedding. A wall-mounted television is situated opposite, with a small table and chair nearby. A fan is positioned to the side, and a compact refrigerator is visible next to the table. Natural light filters through sheer curtains.

Private room in Chicago

4.92 out of 5 average rating, 274 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.