Vacation rentals in Monroe Harbor

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

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

Plymouth Studio Suite with Gym, Rooftop, and Lobby

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers.

Kasa | 2BD Near McCormick Place | 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.

The South Loop Reserve I Sleep 6 I Top Rated

Modern & ultra spacious 2-bedroom loft in Chicago's South Loop. Central location to Grant Park, Soldier Field, Museums, McCormick Place and more! With a walk & transit score of 97, enjoying Chicago's fantastic restaurants, bars, and shopping options is a breeze. Our loft gets incredible natural light, has luxuriously tall ceilings and plenty of room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide.

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.

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!

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.

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

Sentral Premium 2BR Apt South Loop Chicago

Feel at home amid the Chicago skyline. Designer details and mid-century style elevate everything you touch. An all-in-one living area gives you plenty of room to live and work. The fully equipped kitchen features marbled quartz countertops and a gas range. Please note that layout, furnishings, and views may vary by unit. A $500 credit card authorization applies at check-in and is released at checkout.

Studio | Loop | Downtown

New listing! A compact studio right by Millennium or Grant Park. Close to transit and easy access to anywhere you need! Equipped with a kitchenette, this efficient little unit is suitable for those who are coming for work or just need a simple place to sleep. There's a queen bed and 1 single air mattress stored away to use as needed. *Noise from outside and train

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!