Vacation rentals in Monroe Harbor

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Top-rated vacation rentals in Monroe Harbor

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An ivy-covered brick facade presents a charming entrance. A black door with decorative window details is centered, flanked by a small garden featuring well-maintained greenery. A gravel pathway leads to the entrance, showcasing the unique character of the historic coach house.

Guesthouse in Chicago

4.86 out of 5 average rating, 444 reviews

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and comfortable...paper products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea! (See layout in "Other Details To Note" below)

An outdoor pool area is surrounded by greenery and lounge seating, with various umbrellas providing shade. Soft lighting enhances the space at dusk, highlighting the resort-style deck and inviting atmosphere for relaxation.

Apartment in Chicago

4.81 out of 5 average rating, 21 reviews

The Chicago Experience - 2BR/2BA Skyline Residence

Welcome to our Downtown Chicago Premier Luxury apartment!! We've really enjoyed ourselves here, and we're sure you will too. We're located right in the heart of the city. Literally walking distance to The Bean & Lake Michigan, and right across the street from Grant Park - home of Lollapalooza. We're also close enough to hear the crowd at Soldier Field, or view NASCAR from our rooftop deck. So you can enjoy the city - not the traffic. And, a state of the art bldg, with every amenity available

Superhost

An outdoor deck is illuminated by soft string lights, creating a cozy atmosphere. Comfortable seating arrangements, including a sectional and armchairs, surround a modern fire pit. The urban skyline serves as a backdrop, showcasing the vibrant city life.

Home in Chicago

5 out of 5 average rating, 6 reviews

Large Luxury House in River North Sleeps up to 10!

Centrally located River North Penthouse in boutique building has everything you would want with city living. 2-story condo ALL 3 bedrooms featuring en-suites and an additional 1/2 bath. Large living room with fireplace expands on to the outdoor deck with beautiful built-in grill, Second story features 2 bedrooms and a bright sun room. Spacious primary cozy fireplace along with steamed shower and jacuzzi tub. So much more with this luxury style living. Steps to all River North has to offer!!!

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, 305 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.

Guest favorite

A shared rooftop deck with views of the skyline features modern seating arrangements and vibrant flower planters. A stainless steel grill is available for outdoor cooking, complementing the comfortable lounge chairs and table set on the spacious tiled surface.

Condo in Chicago

4.9 out of 5 average rating, 134 reviews

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Superhost

A serene indoor pool area is highlighted by tall glass walls, allowing natural light to illuminate the space. Cozy seating with soft cushions is arranged around the pool, while overhead greenery and pendant lights create a calming atmosphere.

Apartment in Chicago

4.72 out of 5 average rating, 162 reviews

Sentral Studio 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

Superhost

A modern studio suite features large windows providing views of the city skyline. A comfortable gray sofa is positioned in front of a wooden coffee table. The sleeping area is visible, showcasing a queen-size bed with bright linens and artwork on the wall.

Condo in Chicago

4.72 out of 5 average rating, 197 reviews

Luxury Studio Apt Near McCormick & Soldier Field

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen Air mattress for 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Superhost

An open living area features a comfortable sofa and stylish accent chairs, arranged around a glass coffee table. A large flat-screen TV is mounted on the wall, reflecting the light from the expansive windows that provide a view of the exterior building and greenery.

Apartment in Chicago

4.89 out of 5 average rating, 44 reviews

Chic 2BR 2BA Condo with Balcony - River North Chic

Welcome to @TheDreamRentals chic 2-bedroom, 2-bathroom condo located in the vibrant River North neighborhood of Chicago! Perfectly situated in the heart of the city, this stylish and modern space offers everything you need for a comfortable stay. Whether you're in town for business, a weekend getaway, or an extended stay, our condo is the perfect home base to experience everything Chicago has to offer. We can’t wait to host you! Chicago Registration Number: R24000119721

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

4.89 out of 5 average rating, 247 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!

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!

Guest favorite

A comfortable living area features a bright orange couch paired with two ottomans. A dining table with four chairs is set against a backdrop of three windows allowing natural light. Textured brick walls complement the modern decor, creating a welcoming atmosphere.

Apartment in Chicago

5 out of 5 average rating, 7 reviews

Long Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi

Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its residents' unique way of saying it. :) This vibrantly curated apartment is designed for comfortable extended stays that may make you consider making Chicago home, or at least make sure you feel at home while you're here. You will be welcomed into a well-appointed space with cozy linens, sparkling clean bathrooms and warm touches at every turn.

Superhost

A modern bedroom features a plush, spacious bed with a tufted teal headboard. Decorative pillows add a subtle pop of color, while a sleek bedside lamp sits on a wooden nightstand. Neutral walls enhance the serene ambiance of the room.

Hotel room in Chicago

4.77 out of 5 average rating, 298 reviews

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable. The perfect location that is just steps away from Grant Park where Lollapalooza 2025 will be held!