Vacation rentals in Monroe Harbor

A spacious living area is depicted, featuring a comfortable seating arrangement with two sofas facing a mounted TV. A wooden coffee table is centered amidst the seating. The light-filled space leads into the dining area and kitchen visible in the background.

4.84 out of 5 average rating, 98 reviews

Private room close to IIT, McCormick free parking2

Private bedroom, share bathroom with one other guest. Queen size bed, mini fridge and 32in Smart TV. Located at historical Douglas area, Chicago landmark . Close to subway station, bus, IIT, McCormick place (25 min walk, or bus #3 , or Uber<$10), loop, museum campus, white socks station. Area is quiet and safe, near restaurants and super markets. Free street parking. The bed room is located on 2nd fl of the house, it has a lock key Roof top patio with downtown view. Washer dryer in basement.

Guest favorite

A tree-lined street in a quiet neighborhood is visible, with well-maintained lawns and charming homes featuring brick exteriors. A single green chair is positioned on a grassy area, inviting relaxation amidst the landscaped surroundings.

Private room in Evanston

4.94 out of 5 average rating, 210 reviews

Welcoming Evanston Home

We have a newly renovated suite awaiting your stay, perfect for one guest. This dedicated entry, private room + bathroom, and tree-lined street are in our quiet neighborhood in beautiful Evanston, just north of Chicago. As international travelers ourselves, we love hosting others from near or far! Enjoy a short walk to cafes, stores, mall shopping, parks, and restaurants. Easy free parking, convenient Uber / Lift rides, and public transportation are also here to make your stay enjoyable.

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.

4.8 out of 5 average rating, 319 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.

A modern living area features a comfortable gray sofa adorned with blue pillows, accompanied by a round glass coffee table with gold accents. The kitchen area in the background showcases sleek cabinetry, stainless steel appliances, and an organized countertop with dishes and a coffee maker.

4.82 out of 5 average rating, 293 reviews

Kasa | Nearby Millennium Park | River North

Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand new high-rise, our modern apartments include state-of-the-art amenities as well as chic details like gourmet kitchens and high ceilings. You’re less than a mile from the Museum of Contemporary Art, The Wrigley Building, and more. Our tech-enabled apartments offer self check-in at 4 pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

4.82 out of 5 average rating, 521 reviews

Florence Room - 3min to CTA, Free Parking, Roomy

The Florence room is one of three rooms in the grotto. The room has a king size bed and full size sofa sleeper for a maximum guest count of 4. You will have access to the kitchen for the microwave, toaster, and stove, along with free Keurig coffee. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms.There is a private mini fridge in your room for food storage. The house is one block from the Kedzie Green line rail station.

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.

4.72 out of 5 average rating, 166 reviews

Sentral Studio Apt in South Loop Chicago

Indoor/Outdoor Resort-Style Pool • Grilling Station • Four-Story Indoor Garden • Fitness Center • Demonstration Kitchen • Pet Friendly w/ Amenities • Co-Working Space w/ High-Speed WiFi • Across from Grant Park • Steps to South Loop Dining & Nightlife • Breathtaking Views of Lake Michigan & the City Skyline Sentral Michigan Ave offers upscale comfort in the heart of Chicago’s South Loop, blending premium amenities with unmatched access to parks, culture, and entertainment.

Guest favorite

4.96 out of 5 average rating, 80 reviews

near festivals & united center

Room in Garfield Park apartment. 2 blocks from green line and bus routes. 20 min train ride to downtown, 15 min bus ride to Douglass Park (Riot Fest) and United Center. Also near California Corridor, Garfield Park Conservatory. You will be sharing the home with myself and my free-roam rabbit. PLEASE do not book this room if you are allergic to rabbits/hay, or if you are mean to animals. Me: chef, sommelier, mixologist. Avid traveler. Really into baseball and Prince.

4.82 out of 5 average rating, 205 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

4.85 out of 5 average rating, 55 reviews

A3-Next to the Train & Downtown

Located at Pilsen which is one of the 12 Coolest Neighborhoods around the world (by Forbes) this is a Private bedroom with a full size bed in a share apartment close to Downtown Chicago (around 15 min by car). Great gastronomy around. Accesible public transportation just 6 min far by walk to the train (Damen Pink Line) We made a very detailed listing so you can know exactly what to expect, don’t book before reading the whole advertisement.

A spacious bedroom is highlighted by a large bed with crisp white linens. Flanking the bed are two wooden nightstands, each topped with unique lamps. A cozy bench is positioned at the foot of the bed, and large windows provide natural light.

4.71 out of 5 average rating, 356 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

Top guest favorite

A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.

Condo in Chicago

4.97 out of 5 average rating, 828 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.