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Vacation rentals in Monroe Harbor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Monroe Harbor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
An inviting outdoor space features a sleek pool with a gentle water feature, surrounded by neat landscaping. The modern two-story structure rises in the background, complemented by a black umbrella positioned near the water's edge, creating a serene atmosphere for relaxation.
Guesthouse in Chicago
4.85 out of 5 average rating, 34 reviews

Andersonville Luxury Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Top guest favorite
The living room is designed for comfort, featuring a spacious sectional sofa and a cozy armchair. A wooden coffee table sits on a striped area rug, while a TV is mounted on the wall. Decorative art and souvenirs are displayed, contributing to a travel-inspired vibe.
Guest suite in Chicago
4.98 out of 5 average rating, 131 reviews

Travelers Retreat in Old Town Chicago

Our garden unit is decorated with treasured souvenirs, maps, art, and decor that we’ve collected from all over the world to create a travel inspired retreat for Airbnb guests. Located in Old Town, a walkable neighborhood with famed architecture, stellar dining, stand-up/sketch comedy, and local shopping. Walking distance to Brown (Sedgwick) and Red (North/Clybourn) line trains. Centrally located between Downtown/River North and Lakeview/Wrigleyville. Adjacent to Gold Coast & Lincoln Park.

Guest favorite
Apartment in Chicago
5 out of 5 average rating, 21 reviews

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Guest favorite
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
4.94 out of 5 average rating, 50 reviews

Sunny Penthouse - Oakwood Beach

Gorgeous top-floor 2-bedroom, 2-bathroom condo in the heart of Bronzeville! With high ceilings and tons of natural light. The fully equipped kitchen has everything you need to cook a delicious meal, or you can enjoy one of the many great dining options nearby. 🌊Take a 15-minute walk to the lakefront and Oakwood Beach. Centrally located near: • Downtown Chicago • Soldier Field & Guaranteed Rate Field • Field Museum & Art Institute • Chinatown, Hyde Park & Pilsen • And much more!

Superhost
A rooftop pool area is showcased, surrounded by modern skyscrapers. The pool features clean lines and metal railings, with a spacious deck made of large tiles. The backdrop highlights the city skyline under a clear blue sky.
Apartment in Chicago
4.78 out of 5 average rating, 67 reviews

South Loop | Rooftop With In & Out Parking | 3

Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bathroom unit is perfect for corporate travelers and families looking for a chic escape in downtown Chicago 🏡💼 🔥 Rooftop Patio W/ BBQ 🍖☀️ 🏊 Rooftop Pool 🌆 🚗 Free In/Out Parking (5-Min Walk to Garage) 🅿️ 🛏️ 2 Bedrooms | 2 Bathrooms 🚿 🛌 2 Queen Beds 🛏️ 💨 1 Inflatable Airbed 🛌 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included 📺

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, 997 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.

Top guest favorite
Apartment in Chicago
4.94 out of 5 average rating, 16 reviews

Great place in the Heart of Pilsen

"This apartment comfortably accommodates 4 adults with 2 bedrooms and 1.5 baths. There's space for 2 additional guests on an inflatable bed. The spacious main bedroom also features a dedicated workspace. Enjoy the beautiful outdoor area/porch that's assigned exclusively to this apartment. Conveniently located, you'll find CTA buses and the train station within walking distance, and you're just steps away from Thalia Hall and a vibrant selection of trendy restaurants and bars."

Top guest favorite
A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.
Loft in Chicago
4.99 out of 5 average rating, 139 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Top 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
4.91 out of 5 average rating, 212 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!

Top guest favorite
Apartment in Chicago
4.96 out of 5 average rating, 51 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.

Guest favorite
A bright living area features a deep green accent wall and polished concrete floors. A plush dark sofa with decorative pillows is positioned facing a television on a wooden stand. A window offers a view of an outdoor space, enhancing the natural light in the room.
Apartment in Chicago
4.94 out of 5 average rating, 102 reviews

Loop Loft-Subway & Art Institute

Urban Elegance Meets Prime Location! Welcome to our chic hard loft in the heart of the Chicago Loop. Experience city living at its finest, where industrial charm marries modern luxury. Features: - Authentic loft with polished concrete floors - Soaring high ceilings - Elegantly furnished Location: - Right in Chicago's vibrant Loop district - Walk to Millennium Park, Art Institute of Chicago, Mag Mile, Riverwalk, and more

Guest favorite
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
4.96 out of 5 average rating, 72 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.

Popular amenities for Monroe Harbor vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Monroe Harbor