Vacation rentals with a balcony in Chicago

4.94 out of 5 average rating, 339 reviews

The living room features a large window allowing natural light to fill the space. A gray sofa sits beside a small glass coffee table, facing two wooden chairs. Colorful art pieces are displayed on the walls, complementing the patterned area rug.

Home in Lake View

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.

4.9 out of 5 average rating, 527 reviews

An indoor mosaic-tiled pool is surrounded by a spacious, elegantly arched ceiling. Soft lighting reflects off the water, enhancing the serene atmosphere. Wooden lounge chairs are placed along the poolside, providing a comfortable area to relax.

Apartment in Uptown

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”

Top guest favorite

A modern living area features a working fireplace framed by a sleek stone wall. An artwork depicting a scenic waterfront view is hung above the fireplace. A decorative basket holds lush green plants, complementing the warm tones of the leather seating and the dark wooden floor.

Loft in Forest Park

4.96 out of 5 average rating, 507 reviews

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.

4.99 out of 5 average rating, 124 reviews

A cozy sleeping area features a neatly made bed with soft gray pillows and a decorative green bolster. A bedside lamp and a small plant add touches of comfort, while a piece of framed artwork hangs on the white wall above the bed.

Guest suite in Pilsen

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).

4.9 out of 5 average rating, 394 reviews

A bright living area features high ceilings and large windows providing natural light. A striped sofa and a minimalist black chair are positioned around a glass coffee table, complemented by a decorative cowhide rug. Art pieces, including an abstract painting, add character to the space.

Loft in Little Italy

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.

4.82 out of 5 average rating, 119 reviews

A cozy living area features a gray sectional sofa positioned across from a light coffee table. A tall indoor plant adds a touch of greenery, while natural light filters through the window, adorned with sheer curtains. A dining area is visible in the background.

Apartment in Lake View

Chic Penthouse In Perfect Wrigleyville Location

Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, Lake Michigan, Lincoln Park, top notch neighborhood restaurants, pubs, and entertainment, and many more! With so much to do in the area and easy access to public transit you're sure to have jam-packed days of exploring and enjoying the city. After a long day, come back to this peaceful apartment to relax, recharge, and prepare to do it all again tomorrow. Book today!

4.81 out of 5 average rating, 286 reviews

A bright living area features large windows allowing natural light to flow in. A comfortable gray sofa and matching armchairs are arranged around a coffee table on an area rug. A flat-screen TV is mounted on a white media console, enhancing the inviting space.

Condo in Logan Square

Renovated 3br Duplex In Logan Square W/parking

Our three bedroom duplex in Logan Square is tastefully decorated and ideally located for traveling families or groups who want to experience everything Chicago has to offer! We're a quick walk to the Logan Square blue line station and close to some of the best restaurants and bars in the city. One garage 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!

Apartment in Lincoln Park

A cozy studio space features a sofa with blue cushions, complemented by a light wooden table and colorful accent wall. Natural light filters through the window, casting soft illumination. A television is positioned on a ledge, with a decorative statue nearby.

4.84 out of 5 average rating, 277 reviews

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!

A private porch is depicted with a small round table and two black chairs. Green shrubs and potted plants add to the natural setting, while a view of tree-lined streets and brick buildings is visible in the background.

4.97 out of 5 average rating, 246 reviews

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).

4.93 out of 5 average rating, 485 reviews

A modern living room is furnished with sleek white leather sofas arranged around a wooden coffee table. A refined fireplace serves as a focal point, framed by an art piece depicting a serene landscape. Large windows allow ample natural light to fill the space.

Condo in River West

The Penthouse 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 CN Traveler (Sept. 2018). Come live alongside Open House Contemporary’s latest exhibition from some of America's finest emerging artists. Enjoy lots of natural light from this Penthouse condo through walls of windows or slide open the balcony doors for a relaxed evening at home.

4.96 out of 5 average rating, 231 reviews

An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.

Condo in West Loop

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!

4.93 out of 5 average rating, 254 reviews

A bright living area features large sliding glass doors that open to a balcony. Two elegant chairs and a cozy couch are arranged around a coffee table. Greenery adds a fresh touch to the space, with softly colored walls creating a calming ambiance.

Apartment in Uptown

Designer 3br with Balcony & Elevator on Clark!

My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago - You'll love the neighborhood - its vibrant food and arts scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city - if work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable.

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Apartment rentals with a balcony

4.91 out of 5 average rating, 384 reviews

A spacious living area is highlighted by a leather sofa adorned with cozy throw pillows and a glass coffee table. Natural light filters through large windows with sheer drapes, illuminating a modern dining table crafted from reclaimed materials. A decorative plant adds a touch of greenery.

Apartment in River West

The Craftsman Gallery at OHC - No Cleaning Fee!

HonoraRating, 5 stars3 weeks ago

I had a great time staying here. Not only does it look exactly like the pictures, but it was even more spacious than it seems in photos. The cleanliness of the space was pristine and spotless. The location is great too; there’s a train station basically a few steps out the front door. There were plenty of amenities including kitchenware, laundry, and toiletries. Matthew was very helpful in giving detailed instructions for check in as well as tips for places to check out in Chicago and the surrounding neighborhood. He was responsive and timely when I had any questions regarding my stay. I will definitely be booking with Matthew again as he has a ton of other awesome listings and I thoroughly enjoyed my experience here!

A modern living area features a comfortable gray sofa facing a circular coffee table. Behind, a sleek kitchen with bar seating is visible, highlighted by stylish light fixtures. A piece of abstract art adorns the wall, and neutral tones create a serene ambiance.

Apartment in North Side

4.81 out of 5 average rating, 244 reviews

Perfect Lincoln Park Retreat - Walk to Depaul!

EmilyRating, 5 stars2 weeks ago

Catherine was a great host - incredibly responsive and her place had everything my husband and son needed for our stay! Great walkable location and clean unit. Will definitely be returning next time we’re in Chicago!

Apartment in Little Italy

The living area showcases a classic leather Chesterfield sofa paired with mid-century armchairs. A round glass coffee table sits atop a black and white cowhide rug. Natural light enters through large windows adorned with sheer curtains, illuminating potted plants and eclectic wall art.

4.82 out of 5 average rating, 498 reviews

Eclectic Artist Designed Sanctuary Heart of Pilsen

JaideepRating, 5 stars2 weeks ago

Daniel’s place is in the heart of Pilsen, and very close to Downtown, Hyde Park etc, with lots of public transport around. The place is spacious with a nice back facing balcony. Daniel was very communicative, and very kindly allowed us an early check in as we had a lot of luggage. Would highly recommend his place to anyone visiting Chicago!

A private garden area is enclosed by a decorative wrought iron fence, featuring stone paths and lush greenery, including climbing vines. A seating area with metal chairs and a small table is situated near a planter, creating a serene outdoor space. Soft light filters through nearby foliage.

Apartment in Noble Square

4.78 out of 5 average rating, 148 reviews

2 Cozy Bedrooms In a Hidden Wicker Park Gem!

BenRating, 5 stars4 weeks ago

Convenient spot right on the train and good bus access around the city. Grocery store a few blocks away and tons of good restaurants and bars within 15 min walk.

4.76 out of 5 average rating, 72 reviews

A bright living area features a white couch with colorful throw pillows, complemented by a patterned area rug. A modern entertainment center holds a flat-screen TV, while a kitchenette with sleek cabinets and bar seating is visible in the background.

Apartment in Wicker Park

Artsy Chicago Abode: Steps to Shops & Restaurants

ColinRating, 5 stars10 months ago

Had a nice stay. Did the trick as a place to sleep while exploring the city. Good location

Apartment in East Rogers Park

A spacious living room is presented with a comfortable green sofa and two light-colored chairs. A large flat-screen TV is mounted on a wooden media console. A round coffee table sits in the center, surrounded by a soft area rug. Natural light filters through sheer window curtains.

4.8 out of 5 average rating, 10 reviews

3 Bed 3 Bath Lakefront Oasis, Parking Included

NathanRating, 5 stars1 week ago

Great stay. The property is tucked away and is away from all the city noise. It was very clean and everyone was really impressed. Thank you Sally for a great stay.

4.91 out of 5 average rating, 560 reviews

A modern living room features a leather sofa and a stylish armchair with a patterned cushion. A unique fireplace with a decorative bull skull above it serves as a focal point. Colorful artwork decorates the walls, adding vibrancy to the space.

Apartment in River West

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

RyanRating, 5 stars3 weeks ago

Place was as described. Close to great local bars and restaurants and the train. Host was very responsive.

A spacious living area features two light blue sofas with contrasting cushions, arranged on a patterned area rug. Natural light filters through elegant window treatments, enhancing the warmth of the hardwood flooring. A grand staircase is visible in the background, framed by archways.

Apartment in Lincoln Park

4.7 out of 5 average rating, 44 reviews

Huge Lincoln Park 6 Bed Duplex with Free Parking!

RaviRating, 5 stars6 months ago

This place is great for large parties. It’s close to bars, restaurants and the main strip of Lincoln Park. Being close to the hub of things means it’s a bit noisier. Not crazy or anything, but if you’re not use to city noise this can be surprising. The bedrooms are laid in a way that not every room is private (glass doors), shared spaces, etc. more of a heads up when you enter into the unit there’s a flight of stairs to get to the unit. Not a deal breaker, but we had someone in a walker which made it a bit more challenging. Would rent this space again!

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House rentals with a balcony

An open and airy kitchen space features a large island with two red stools. A white refrigerator and stove are positioned against a textured wall. A pink shark sculpture and a vibrant yellow cabinet add playful color, while a large window invites natural light into the room.

4.9 out of 5 average rating, 203 reviews

ALOHA Penthouse in Wicker Park w/Backyard Patio

AlishaRating, 5 stars1 month ago

Liz was a wonderful host. Informative and detailed. She has literally thought of everything you would need for the stay and then some! Fully stocked cleaning supplies, toilet paper, linens and kitchen items. Very clean and neat place that allowed for everyone to have a space of their own and not feel cluttered. Thank you for such a wonderful experience.

4.94 out of 5 average rating, 18 reviews

An open living area features a round dining table with black chairs and a decorative centerpiece. A comfortable seating arrangement with a dark sofa and accent chair is visible, with soft natural light streaming through large windows adorned with sheer curtains.

Home in Uptown

6 Bedrooms In Beautiful Sheridan Park!

JeromeRating, 5 stars3 months ago

Had a great stay over St. Patrick’s day weekend. The apartments are in a very walkable area with great access to public transportation. Fenton was also very quick to communicate and gave clear instructions. 10/10 would recommend to anyone.

A light-filled living room features a neutral-toned sofa and a large marble-top coffee table on a colorful rug. An arc floor lamp and a decorative potted plant add dimension, while framed artwork adorns the walls, creating a relaxed and inviting space that connects to a dining area beyond.

Home in Tri-Taylor

4.65 out of 5 average rating, 43 reviews

Newly Updated Vintage 6 Bedroom Single Family Home

KrisRating, 5 stars3 weeks ago

My stay at this property was exactly as I expected and more. It was as described and was very much a vintage beauty. We felt right at home and had a great time. It accommodated my large party and the icing on the cake was all the great restaurants. We will definitely stay again in the future.

Top guest favorite

A bright dining area features a long wooden table surrounded by six blue chairs. A modern chandelier hangs above, illuminating the space. In the background, a staircase leads to the upper level, while a cozy living area is visible, providing an open and inviting layout.

4.97 out of 5 average rating, 36 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

JohnRating, 5 stars2 weeks ago

Great place and stay! Location is amazing!

A spacious living room features a comfortable gray sectional sofa facing a wall-mounted television. A round coffee table sits on a textured area rug, surrounded by two accent chairs. Natural light filters through sheer curtains, complemented by indoor plants near the windows.

Home in Des Plaines

4.29 out of 5 average rating, 24 reviews

Spacious Retreat Near Convention Centers

Adil KhanRating, 5 stars1 month ago

Really nice home in a great location. Everything checked out. The only thing you need to worry about is that there’s just one restroom in the house. Apart from that everything was great!

4.95 out of 5 average rating, 152 reviews

Home in Logan Square

The Grand Kimball Lodge, Logan Square, Sleeps 14

AlexRating, 5 stars3 weeks ago

Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!

4.87 out of 5 average rating, 129 reviews

A stylish living area features a combination of striped and solid-color chairs, a plush area rug, and a modern coffee table. Large windows provide natural light, while a decorative fireplace adds to the cozy ambiance of the space.

Home in Lake View

Soak Up Mid-Century Style in Wrigleyville and Boystown

ShelbyRating, 5 stars4 weeks ago

My family and I really enjoyed staying here. It is in a really cute neighborhood and looks like the photos described. Very walkable to things. Everything we needed for our stay was in the house and accessible to us. It is mentioned in the listing that street parking is available but not reserved spaces. Since we knew this, we planned ahead and found parking in the neighborhood which I strongly recommend doing. The street parking was hard to come by on a weekend. Again, this was not an issue for us but do plan ahead. Matt was a great host and if we ever are in town for a cubs game, we would absolutely stay at this place again. It has so much character and they have very clearly maintained the space well. Also we appreciated how extremely clean everything was.

A spacious dining area features a large wooden table surrounded by ten blue upholstered chairs. Bright lighting illuminates the room, enhanced by a contemporary chandelier. Large glass doors provide an inviting view of the outdoor space, framed by greenery and patio furniture.

4.6 out of 5 average rating, 10 reviews

Wicker Park 4bd/3ba, Steps from Cta, Parking Incl

TylerRating, 5 stars3 months ago

Had a great stay at this Airbnb! The house was fantastic, located in a perfect spot, and the host was very responsive and helpful. Highly recommend!

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Condo rentals with a balcony

4.92 out of 5 average rating, 37 reviews

An open living area features a modern design with a gray sofa and two accent chairs. A wooden coffee table is centered on a light-colored floor. Large windows bringing in natural light are dressed with sheer curtains, complementing a decorative stone wall and wall-mounted television.

Condo in West Town

Newly Designed 3bd In Heart of Ukrainian Village

TeriRating, 5 stars1 week ago

The host was excellent at communicating and very responsive! I greatly appreciated her flexibility. Our kids loved the park in the back yard.

4.83 out of 5 average rating, 362 reviews

A living area features two tufted gray sofas and a glass coffee table atop a patterned rug. The space is illuminated by natural light from large windows, with decorative accents including throw pillows and a cozy ottoman.

Condo in North Side

Chic and Charming Vintage Condominium in Lincoln Park

PatrickRating, 5 stars2 weeks ago

We had a terrific stay and would definitely recommend it to others. Great location, especially if you are doing anything around Lincoln Park, DePaul, etc. The dedicated parking space was really helpful (there are 2 of them, but we only had one car). We had six people and were very comfortable. Colin is very responsive as well.

4.84 out of 5 average rating, 186 reviews

An open layout living area showcases exposed brick walls and a modern kitchen. A dark green sofa with orange accent pillows is featured, accompanied by two black chairs. A round area rug sits beneath a glass table, with a large vintage map of Chicago adorning one wall.

Condo in Wicker Park

Loft-Like Wicker Park Condo Steps from the Cta!

LaurenRating, 5 stars1 month ago

Tom’s place was exactly what we needed for a weekend in Wicker Park! The location was perfect to enjoy restaurants and stores, and the ease of access with the keypad was great for check-in and coming/going. The unit was very clean and spacious, and having a dedicated parking spot was amazing! Would definitely stay here again.

A warm living area features exposed brick walls and hardwood flooring. A comfortable leather sofa faces a wall-mounted TV, with a stylish round coffee table in the center. Soft light filters through sheer curtains, and a potted plant adds a touch of greenery.

Condo in Tri-Taylor

4.87 out of 5 average rating, 382 reviews

3 Bedroom Vintage Hideaway In Little Italy/uic

AlyssaRating, 5 stars1 month ago

We had a great time staying at Matt and Christy’s place. The neighborhood was quiet, providing space to rest after busy days. The apartment had a lot of charm and was a comforting place to return to. It took us about fourteen minutes to walk to the closest metro station, but overall was centrally located for our purposes. The hosts are helpful and were quick to respond when we needed additional supplies.

4.83 out of 5 average rating, 170 reviews

A modern living area features rich purple tufted sofas arranged around a glass coffee table. A large flat-screen TV is mounted on the wall, while windows allow ample natural light, framing views of the cityscape. Decorative artwork adds color to the neutral walls.

Condo in Little Village

Modern, Spacious 3br Apt Minutes to Downtown!

AnthonyRating, 5 stars2 weeks ago

A great host who responded promptly and was welcoming !