Vacation rentals with a fireplace in Downtown Chicago

4.96 out of 5 average rating, 114 reviews

The exterior of a red brick building showcases a classic architectural design with white-framed windows. The front steps lead to a dark door, surrounded by well-maintained shrubs and small plants. Clear blue skies create a bright backdrop to the inviting facade.

Condo in Chicago

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE!! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops. Free parking on Lawndale Ave.

4.92 out of 5 average rating, 381 reviews

A book titled 'Haunts of the White City' is displayed against a dark surface. The cover features a vintage-style house and a large moon, with the title and subtitle prominently shown in a contrasting font. The overall color scheme emphasizes a mysterious and historical theme.

Apartment in Berwyn

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

4.98 out of 5 average rating, 158 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

4.92 out of 5 average rating, 71 reviews

A compact workspace is situated near a fully equipped kitchenette. The desk, affixed to the wall, is complemented by a black office chair. An oven is integrated into the cabinetry, while a coffee maker is positioned on the countertop beside a sleek trash can.

Guesthouse 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.

4.98 out of 5 average rating, 154 reviews

An outdoor space is presented with two dark chairs arranged around a circular fire pit. A white fence provides privacy, and a stack of firewood is located nearby. The paved ground offers a sturdy surface for seating and relaxation.

Guest suite in Chicago

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*

4.94 out of 5 average rating, 208 reviews

An inviting dining area features a round table set for four, complemented by modern wooden chairs. The sleek kitchen, equipped with stainless steel appliances, is illuminated by recessed lighting. Large windows bring in natural light, while a potted plant adds a touch of greenery.

Condo in Chicago

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.

Superhost

A vintage-style bathtub is displayed, featuring clawfoot legs and a polished chrome faucet. Hexagonal tiles line the floor, complementing the simple, neutral tones of the bathroom. A soft bath mat is positioned in front of the tub, enhancing functionality and comfort.

Apartment in Oak Park

4.88 out of 5 average rating, 402 reviews

Charming Chicago-Style, Vintage, Tv NFL PASS

→ 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

4.97 out of 5 average rating, 144 reviews

A wooden patio area features a central fire table surrounded by four cushioned seating chairs. Glasses of wine rest on the tabletop, inviting relaxation. A partial view of neighboring roofs is visible in the background, providing a sense of privacy in this outdoor space.

Condo in Chicago

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

4.98 out of 5 average rating, 356 reviews

The exterior of a historic brick building is framed by lush green trees and plants. A decorative wrought-iron gate leads to a set of stairs, which rise to a large wooden front door. Sunlight filters through the foliage, creating a serene entrance.

Home in Chicago

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.

4.94 out of 5 average rating, 171 reviews

South Loop 3Br/2Ba Condo with Balcony & Parking

Welcome to our stylish 3-bedroom, 2-bathroom apartment in the vibrant South Loop neighborhood! Perfect for families, friends, or business travelers, this spacious unit comfortably sleeps up to 6 guests. With a private balcony, free parking, and all the amenities you need, it’s an ideal base for your Chicago getaway. Book your stay today and experience the best of Chicago from the comfort of this modern, spacious apartment!

A living area features a large television mounted above a white fireplace with an electric insert. Decorative elements include a vintage mirror and a clock on the wall. A black tufted ottoman is positioned beside the fireplace, with illuminated warm tones from a nearby hanging light.

4.86 out of 5 average rating, 312 reviews

Charming loft style suite

Original loft style 2nd floor apartment with private entrance. Thoughtfully furnished two bedrooms with a queen bed in each room. Plus a build in king size tatami in family room. A eat-in kitchen is convenient for basic warm up/cooking. There is a mini fridge, coffee maker and microwave. 10-20 Minutes drive to Loop, Museum Campus, Mc Cormick Place, Illinois Medical District, Soldier Field, White Sox& United Center.

A private rooftop patio is displayed, featuring a seating area with bright orange cushions on a dark wicker couch. A glass table is centrally placed, surrounded by panoramic views of the Chicago skyline under a partly cloudy sky.