Vacation rentals with a fireplace in Wicker Park, Chicago

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Top-rated fireplace rentals in Wicker Park, Chicago

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Superhost

A spacious rooftop lounge area features a comfortable sectional sofa with neutral cushions, set against a backdrop of the city skyline. The view includes prominent skyscrapers and a clear sky, offering an inviting space for relaxation.

Apartment in Wicker Park

4.91 out of 5 average rating, 285 reviews

Gorgeous Penthouse with Stunning Views from Private Rooftop

Welcome! We are young professionals opening up our 2 bedroom apartment to warm and down-to-earth travelers. We'd like to help you fall in love with Chicago! LIVING SPACE: Top floor condo with a great view of the neighborhood tree-lined street. Moderately large open space with hardwood floors, a comfortable and inviting atmosphere, and plentiful natural light. You can also relax on our private rooftop. KITCHEN: You are free to use the full kitchen. BEDROOMS: Two bedrooms with ample natural light and large closets. Fresh sheets, pillow, bath soap, and bath towels will be provided. BATHROOMS: 2 bathrooms (1 is a master bathroom with shower and bathtub) for guests. Central A/C is provided in the warm months and central heat during the cooler months. We live in Chicago and are happy to help if you need something. Beautiful walking-friendly Wicker Park showcases Chicago's culture, arts scene, and food and entertainment. Explore diverse nightlife and bars, historic buildings, countless vintage shops and boutiques, and street festivals in the warmer months. TRANSPORTATION: The condo is approximately a 30+ minute direct train ride from O'Hare airport and ~40+ minute train ride from Midway airport (1 transfer) using the "El" train. Getting to our condo from O'Hare is direct as we live right off the 'DIVISION' stop on the BLUE LINE. From Midway, you would need to transfer from the ORANGE LINE to the BLUE LINE. We are a fairly quick train or bus ride to the Loop and River North (for access to "downtown" cultural and city attractions) as well as other popular Chicago neighborhoods such as Ukrainian Village (walking distance), Bucktown (walking-bike distance), Gold Coast, Old Town (1 single bus, no transfers), Greektown, West Loop (quick Uber), Lincoln Park, Lakeview (bus), and Logan Square (quick "El" train ride). PARKING: Free parking can be found on Augusta Blvd (with exceptions on certain hours/days for street cleaning). Additional free parking can be found just a bit further on Cortez and Paulina. We look forward to providing you with the Wicker Park and Chicago neighborhood experience. Once you arrive, you'll get an even better picture of how phenomenal this location is.

Superhost

A spacious wooden rooftop deck is presented, featuring a built-in bench along the railing. The city skyline is visible in the background, showcasing various buildings under a partly cloudy sky. The deck offers ample space for outdoor seating and relaxation.

Apartment in Wicker Park

4.78 out of 5 average rating, 284 reviews

Private Studio Apt in the Heart of Wicker Park!

*No Hidden Cleaning Fees or Deposits* Enjoy Wicker Park with your own private renovated studio apartment! The apartment comes complete with a large living space, including a twin day bed which can be pulled out and converted into a king size bed. The kitchenette has a fridge & microwave. There is A/C, fast WiFi, TV, new bathroom, laundry facilities and a communal rooftop deck with skyline views. Close to EL train, highway, shopping, restaurants, nightlife, cafes, 606 bike trail and more!

Guest favorite

A wooden deck features two intricately designed metal chairs and a small table. Potted plants are placed nearby, and greenery from a tree is visible through the railing, providing a natural ambiance.

Apartment in Humboldt Park

4.96 out of 5 average rating, 298 reviews

Logan Square 2nd Floor Chicago Victorian

Walk up the stairs to your sunny 7 rm, 2 queen bedrooms with full kitchen & 10' ceiling. 1/2 block the 2.9 mile walking/running/biking 606/Bloomingdale Trail that travels over other neighborhoods you can explore. In 2024, 'Time Out Magazine' voted Logan Square, one of the top 'Cool Neighborhoods in the World'. Walking distance to many restaurants, bars, breweries (beer & coffee) 20 min. walk to the Blue Line 'L' for O'Hare or Downtown. Rosa's - 'Chicago's Best Blues Club' - NY Times- 3 blocks

Guest favorite

A vibrant street scene features classic brick buildings with architectural detailing lining both sides. A large sign reading 'BOOKS' is prominently displayed. Cars are parked along the curb, while shops and cafes create a lively atmosphere under a clear blue sky.

Apartment in Wicker Park

4.96 out of 5 average rating, 151 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Superhost

A bright red door stands prominently against an exposed brick wall. Black marble steps lead up to the entrance, creating a contrast with the light wooden floor. A coat rack with a sleek design is positioned nearby, enhancing the functional space.

Condo in Humboldt Park

4.86 out of 5 average rating, 474 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed -> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

Top guest favorite

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 West Town

4.97 out of 5 average rating, 145 reviews

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!

Top guest favorite

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 West Loop

4.98 out of 5 average rating, 356 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.

Top guest favorite

A spacious bathroom features light-colored stone tiles covering the walls. A modern bathtub is set against the wall, complemented by a sleek faucet. A showerhead is mounted above, providing ample water pressure. Personal toiletries are neatly arranged on the side of the bathtub.

Condo in Humboldt Park

4.92 out of 5 average rating, 265 reviews

Modern/Spacious 2BR/2BA West Town

Light, airy and luxurious, our duplex has a self-contained, 1400 sq. ft. 2nd floor with a private street entrance. There are two bedrooms and two baths. The master bedroom has a fireplace, a private balcony and a huge bathroom ensuite. In addition there is a dining room and living room. Minimal kitchen facilities include small fridge and micro. Easy commute downtown- 20 by car, 25 by bike and 30-40 minutes via public transportation. Close to hwy and public trans.

Guest favorite

Home in Wicker Park

4.93 out of 5 average rating, 363 reviews

Amazing Penthouse Skyline Views!

Duplex 3 BD 3 BA Penthouse in the heart of Wicker Park. 2 minute walk to the Damen Blue line, bars, restaurants, boutiques, live music venues and shopping. Private elevator opens into Unit. Full kitchen, wet bar, large deck - Amazing Views! 2 Large Decks, both with amazing views of the Chicago Skyline. 3 Bedrooms - 2 Master Suites with large private baths and a large 3rd Bedroom with a full bath across the hall. Wicker Park is an Amazing neighborhood!

Top guest favorite

A three-story brick building is presented, featuring large windows and accent balconies adorned with plants. A stone pathway leads to the main entrance, while a small garden area is visible at the base, surrounded by a decorative black fence.

Apartment in Wicker Park

4.96 out of 5 average rating, 158 reviews

Hip Chicago Condo in fun shopping and dining area

Spacious 2 bedroom, 2 bath condo in ideal Wicker Park location-walk to everything including CTA/Blue Line, shops, restaurants & Division St. Night Life!! Highly upgraded with hardwood floors, granite countertops & breakfast bar, SS appls, luxurious marble baths, Jacuzzi tub & wood burning fireplace. This condo also features a large walk-in-closet, washer and dryer, private outdoor covered terrace. Free street parking. *Send PM for one night stays

Top guest favorite

A modern bathroom features a walk-in shower beside a black sink mounted on a gold frame. The walls are tiled in light blue with a sleek mirror above the sink. A black and white hexagonal floor adds contrast, while light fixtures provide illumination.

Condo in Wicker Park

5 out of 5 average rating, 105 reviews

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.