Vacation rentals with a balcony in Cook County

Stunning Old Town Penthouse with Private Rooftop

This listing is for the entire building, which is the combination of a penthouse loft (3BR) and the unit directly underneath (2BR), easily connected by private stairs. You will also have a private rooftop deck. This is a beautiful 4,000 sq. ft penthouse loft combined in the heart of downtown Chicago. The building is next to "Magnificent Mile" and steps away from amazing restaurants, comedy clubs (Zannies, Second City), theaters, boutique shopping, public transportation (red line, and 156 bus line), bars and just four blocks from the beach. **Please be aware there are 45 steps to get into the unit (2 flights). This building is truly one of a kind. Built in 1897 and completely renovated in 2016 this unit has exposed brick, 20 foot ceilings and 120 year old barn wood floors capped off with a rooftop deck overlooking Willis (Sears) Tower. 5 bedrooms - 4 with king beds and one with 3 single beds (a bunk bed and a separate single) Also a nook area with a twin bed, built in reclaimed wood; very cute, unique, and comfortable sleeping area! 4 full bathrooms Two full kitchens and two full living rooms. Penthouse master bedroom- Fit for a king. Located on balcony level overlooking living room. Vintage french doors open to balcony. Furnished with a tempurpedic king sized bed and 50 inch TV. Attached to marble bathroom with jacuzzi and all-marble rain forest dual shower head steam shower. Enjoy Kohler faucets and heated floors. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Penthouse second and third bedrooms - Spacious and comfortable, king bed in one, three singles in one. Nicely outfitted with crown molding and large closets. Second Bathroom - Marble floors, classic European style and granite counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Fourth bedroom - Furnished with a cloud like king sized bed, crown molding, exposed brick, and large closet. Remote controlled overhead fan. Connected to a brand new subway tiled bathroom with antiqued brass hardware and a jacuzzi. Enjoy heated floors here as well. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Fifth bedroom - Spacious and comfortable, with cloud like king bed. Crown molding, exposed brick and large closet. Remote controlled overhead fan. Fourth Bathroom - Subway tiled walls with antiqued brass hardware here as well, classic European style marble counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Extra amenities include two push button fireplaces, vintage 1950 Valley pool table, dartboard, surround sound stereo system, PS3 (with movies and games), blu ray, board games and two 60-inch hanging TVs both equipped with HBO, Netflix, Showtime, TiVo, and Amazon each in their own full sized living rooms. Two full laundry rooms in building with irons and ironing boards. Last but not least is the private rooftop deck. This view is absolutely magnificent. Your first walk out onto this large spacious rooftop deck will leave you speechless. It boosts a comfortable couch, grill, and large table all adorned with round draping bulb lights going from corner to corner of the deck, with a full 360 degree view of the Chicago skyline. You will never forget your Chicago visit when you are on the roof deck after the sunsets and the city lights fill up the sky. Spoil yourself in the Windy City. There is nothing else like this in the city. Upon arrival, a welcome packet that will explain to you all about the features of the penthouse and how to maximize your time while staying here. Anything from how to work the jacuzzi to how to operate the electronics is outlined and at your disposal when you walk in the door. We are also pet friendly. While exploring the city we are very centrally located we recommend walking or biking to places like Michigan Ave and the Oak Street beach. A wonderful place to spend an afternoon! There is a parking garage across the street for $26/day located at 1225 N Wells Street. There is also metered street parking. Old Town is an historic area of Chicago right in the middle of the action. It's a perfect base from which to experience the city. Walk or bike to interesting places like Michigan Avenue and the Oak Street Beach. We are very close the the Red Line El train and numerous buses and a divvy bike station. Parking garage across the street. Uber and Lyft are choice methods as well. However, being in the heart of Old Town there is plenty within walking distance.

The Roscoe House near Wrigley Field

Enjoy stylish living in the Roscoe House, an updated 1888 Victorian where wood and granite counter tops meet walnut shelves and vintage finds, mixed with original art. The house includes a library, patio, and fully stocked gourmet kitchen. *nearby train track construction was recently mentioned in 2 reviews; the city of Chicago seems to have moved on to a new section of the track, yay! If this changes we will do our best to update you!* Bringing kids? We have a pack and play with organic cotton sheets, blow up toddler bed, sound machines, high chair, baby gate, play kitchen, toys and books. FYI: There is a Craigs List scammer using our listing photos-- Beware! We love art and design and hope our home reflects that. This newly remodeled modern space is a 3 bedroom house, each with a private bathroom and flat screen TV. (3br 3 bath) There is also a queen pullout sofa if you have a larger group- we can accommodate up to 8 people. We provide all sheets, towels, and parking permits for street parking where you can usually find a parking spot within the block radius. The living room is perfect for hanging out- enjoy the 55in SmartTV /Netflix,Amazon prime accessible or read a book or play a game in our library, and cook in the fully stocked kitchen or BBQ on our patio. The home has central air throughout- so heat in the winter and A/C in the summer. All the rooms have ceiling fans for the in between seasons. Want to be out? You're a 5-10 minute walk to many great shops, restaurants and bars. We are 20 minutes to downtown via the Red line EL train, 5 minute walk to Wrigley Baseball Stadium, 7 minute walk to Southport Street where all the family restaurants and great shops are, and a 10 minute walk to Boystown. The Roscoe House is the perfect place for your stay in Chicago! Remember though, with all this great access to city fun- you will be in the city, which means you will hear the train pass behind the house (3 lots over) and if the windows are open, you might hear the neighbors. Most say that the train sounds like a nice woosh to lull you to sleep :) Permit street parking is available (we can give you a permit)**A NOTE ABOUT THE PARKING PERMITS: Be sure to enter the date and time on the sticker for every day you park. They are only good for one night, and if you do not enter the date and time in pen (careful not to smudge) you will be ticketed!!. Of course we have a laundry room and wifi. Have a baby? We have all the gear. Looking for something a little cheaper? We have another listing, equally as beautiful, just as close to the same great shops and restaurants. Minutes from the Brown line Addison stop. Copy and paste this link to view/book: http://airbnb.com/rooms/1084001 See our recent feature in Houzz! (website hidden)(phone number hidden)/list/my-houzz-eclectic-industrial-style-in-a-charming-chicago-home Living room, laundry, library hall, kitchen, patio with grill Youre always welcome to call or text us, either through the AirBnb message thread, or to our cell phones directly. We have a contractor and house manager nearby if we are not able to meet you at that moment. Walk to great shops, restaurants, and bars in less than 10 minutes. Visit Wrigley Field nearby, or explore Southport Street, which boasts family-friendly restaurants and great shops. Boystown is a 10-minute walk, too. 7 minute walk to the Belmont stop on the Redline EL train You can hear the woosh of the train as it passes behind the house. It is urban living and will lull you to sleep..... PLEASE NOTE WE DO NOT POST ON (SENSITIVE CONTENTS HIDDEN). ANY POSTING ON OTHER WEBSITES IS A SCAM, PLEASE NOTIFY US IF YOU HAVE SEEN ONE.

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Walk to Oak Park from a Bright Madison Street Loft

Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

Cozy Hideout in Art Filled Chicago Neighborhood

Your private guest suite is newly renovated. You will have a private room with your own keypad entrance, thermostat and bathroom, T.V. with internet access, mini fridge, serving ware, coffee maker, fruit and yogurt in the fridge! We also have a toaster oven in case you want to warm up leftovers. You will only have access to your room, which is comparable to a short term stay hotel room, but way cooler. send a text or message me and I'll respond as soon as I can The Pilsen neighborhood got voted one of the 12 coolest neighborhoods in the world in 2018, according to Forbes magazine. There’s venues, studios, and bars booming with more culture all only blocks away. Uber / Lyft is a great way to get anywhere quick - usually a 15 min ride to downtown. Public transit options are the CTA El Train (Pink Line 18th stop is 0.7 mile walk from our house) or CTA Bus (18th & Racine stop is a block away). Once you’re at the transit stop both options take about a 20 - 30 minute to downtown. There are other bus lines nearby that take you other places (i.e. McCormick Place) - feel free to ask us for help when you arrive. Street parking is free in certain areas for those who are driving. Please message us and we’ll direct you where to park. We are a 20 minute cab ride from Midway International Airport and 40 minutes from O'Hare without heavy traffic, double these estimates if traffic is heavy (rush hour, accidents, etc).

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

The Woodsman's Gallery at OHC - No Cleaning Fee!

Welcome to Open House Contemporary! Chicago's best Airbnb! Featured in Architectural Digest (Aug. 2018) and as one of Bobby Berk's (Queer Eye's designer extraordinaire) top 10 Airbnbs in Condé Nast Traveler (Sept. 2018). Come live alongside Open House Contemporary’s latest exhibition from some of America's finest emerging artists. Relax in the unparalleled luxury of the Woodsman Gallery's modern decor and all the comforts of home while being surrounded by gorgeous contemporary art.

Can't Beat This 2min Walk to Wrigley!

My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Updated Designer Duplex In Fulton Market W/parking

We completed our luxury renovation in kitchen, bathrooms, and patio with a fire pit! We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

Logan Square Beauty with 2 Bedrooms W/parking

Our two-bedroom condo is beautifully appointed and has vintage charm everywhere you look. You'll have access to a shared backyard, and all of the amenities of home - while being a 10 minute walk from some of the hottest bars and restaurants in Chicago. One garage parking spot is available during your stay. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!