Vacation rentals in Monroe Harbor

Highrise Hideout (2BD / 2BA)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

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

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.

Walk to it all in Pilsen

This 2 bedroom, 1 bath rehabbed apartment is in Chicago’s vibrant Pilsen neighborhood—rated one the coolest neighborhoods in the WORLD by Forbes! It is a short walk to award-winning restaurants, boutiques and cafes on the 18th Street Corridor and a 5 minute walk to the CTA train that will have you to the Loop in about 10 minutes. It was gut rehabbed in 2017, and it contains an updated kitchen and bathroom, central heat and air conditioning, and a private deck off the kitchen.

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!

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

Cozy newly renovated apartment in Bridgeport

Welcome to your perfect home away from home in Bridgeport, Chicago 🏡 This newly renovated cozy 1-bedroom, 1-bathroom apartment offers a comfortable, inviting space just 10 mins to downtown Chicago. Located couple minutes from Chinatown Whether you're here to catch a White Sox game or immerse yourself in the vibrant local food scene and culture, this location is ideal for exploring the best of Chicago. FREE PARKING 🅿️ NO PARTIES.

Spacious & serene in hip spot. Sleeps 4.

Located in the heart of Pilsen, a vibrant neighborhood rich in Mexican arts/ culture, and an emerging hipsterville. Check out art gallery crawls, award winning restaurants and local taquerias. Thalia Hall (3 blocks away) w/ indie and major musicians. 7 mins via car to downtown or 2 blocks to train/bus. Mask wearing is optional. Guests are not required to wear masks. Chicago Registration #: R21000069179

Chicago River Room, near Med Ctr

R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.

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.

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 Blue Room

A spacious single-family home; minutes away from Midway Airport (train station), within walking distance from gorgeous and dog-friendly parks, and walking distance of plentiful of supermarkets and convenience stores. Downtown Chicago is just about 40 minutes away from a train ride.