Holiday rentals with a fireplace in South Side

4.91 out of 5 average rating, 231 reviews

Guest suite in Chicago

Bike the Lakefront from a Sleek Urban Retreat

Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.

4.83 out of 5 average rating, 170 reviews

Guest suite in Chicago

West Loop 2 bedroom with outdoor space

2 bedroom 1 king and 1 queen / 1 bath condo in 2 unit building (we have 2 rollaway twins for additional beds) located 1/2 block from Union Park, if you aren't familiar with the area Union Park ends Randolph AKA Randolph Row with several Michelin Restaurants like Little Goat or Smyth either on or 1 block from Randolph. 2 1/2 blocks to the green pink line or 1/2 mile to the Rush/UIC Medical District. Everything you need for full access to the city. This is the top floor of a 2 unit building.

4.89 out of 5 average rating, 18 reviews

Penthouse w/ Massage Chair Near McCormick.

Experience luxury and comfort inspired by an avid traveler and frequent Airbnb user. Enjoy complete privacy in this stylish condo, featuring a spacious living area, fully equipped kitchen, serene bedrooms, and modern amenities. Nestled in historic Bronzeville, it offers easy access to major attractions in Chicago. Highlight: Zero Gravity massage chair, perfect for unwinding and rejuvenating after a day of exploring the city. Stay with me for a serene, spacious retreat designed for your comfort.

4.86 out of 5 average rating, 153 reviews

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and etc. Hotel style, no kitchen

4.93 out of 5 average rating, 81 reviews

Guest house in Chicago

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

Top guest favourite

Guest suite in Chicago

4.98 out of 5 average rating, 161 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

4.91 out of 5 average rating, 351 reviews

Guest house in Chicago

Private Studio in Bridgeport, Chicago

A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.

4.94 out of 5 average rating, 214 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

5 out of 5 average rating, 37 reviews

Flat in Chicago

Private Duplex w/ Theater + Games | Near UChicago

Enjoy endless entertainment with family and friends in our spacious 2-level home, equipped with central air and heating! The lower level is your fun zone—featuring a 120" projector for movies, a retro arcade game, ping pong, board games, a bedroom and bath, and a reclining sectional for movie nights! Upstairs, you'll find 2 bedrooms, a full bath, a patio with new furniture, and a fully stocked kitchen with appliances and complimentary coffee. Everything needed for a fun, comfortable stay.

4.88 out of 5 average rating, 407 reviews

Flat in Oak Park

Charming Chicago-Style, Vintage, Cable 42-1

→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Experience vintage Chicago style living in this richly characteristic brick building, situated in a safe and quiet neighborhood. ★ Property Features: • One block away from the Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable and option to use other apps • Free Laundry Room • Free Parking

Top guest favourite

Home in Chicago

4.98 out of 5 average rating, 358 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.