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Holiday rentals with a patio in Downtown Chicago

Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb

Top-rated Holiday Accommodation with Outdoor Verandahs in Downtown Chicago

Guests agree: These Holiday Homes with Outdoor Verandahs are highly rated for location, cleanliness and more.

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Apartment in Chicago

4.87 out of 5 average rating, 108 reviews

Idyllic Lakefront Sanctuary W/ Unforgettable Vista

From the moment you step into the living room of my lakefront home, your breath will be taken away by the incredible scenery outside of the huge windows. Let the gentle sounds of the lake relax you and clear your mind during your tranquil stay. The interior is just as stunning with professionally designed decor, completely new appliances, & thoughtfully provided amenities. You will want for nothing during your stay and may not want to leave! Don't miss out on a true lakefront gem, book today!

Guest favourite

Apartment in Oak Park

4.92 out of 5 average rating, 108 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Guest favourite

Apartment in Chicago

4.97 out of 5 average rating, 37 reviews

Fulton House #1 - Studio Only

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced studio has the business-travel amenities you want: ultra speed wifi, work station, top tier dining options within steps, Nespresso coffee maker, bottled water and more. Paid parking next door $20/day, subject to avail - inquire in advance.

Guest favourite

Condo in Chicago

4.96 out of 5 average rating, 125 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.

Guest favourite

Apartment in Forest Park

4.88 out of 5 average rating, 102 reviews

Home in Forest Park upstairs.

In this cozy newly renovated apartment you will have a fully equipped kitchen, in unit laundry, super fast WiFi connection and a large back yard.. Conveniently located 30 minutes from O'Hara International Airport, 20 minutes from Downtown Chicago via I-290, and 40 minutes away from Midway International Airport. Forest Park is a very safe, vibrant and diverse suburb of Chicago. You will be within walking distance of many different restaurants, boutiques, bars, parks, and public transit.

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 38 reviews

Private City Hideaway

Park in the private garage and walk to restaurants, coffee, bars , cafes and shopping. 10 minutes to the train! All outside your front door from this entirely private extra large one bedroom city apartment. Well appointed kitchen, free laundry, wi-fi, heat and air cond. No parking worries with included garage parking!! Click SHOW MORE - for detailed location information - Click SHOW MORE Wrigley Field 8 minutes Uber 15 public transport 30 walking NOTE: no smokers no visitors

Guest favourite

Apartment in Berwyn

4.88 out of 5 average rating, 145 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Guest favourite

Condo in Chicago

4.96 out of 5 average rating, 179 reviews

Updated Designer Duplex In Fulton Market W/parking

UPDATE: We just completed our luxury renovation March 2023! New kitchen, bathrooms, and patio with a firepit. 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!

Guest favourite

Apartment in Chicago

4.83 out of 5 average rating, 213 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!

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 206 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).

Guest favourite

Home in Bridgeport

4.86 out of 5 average rating, 51 reviews

Cozy Bright Quiet Boho-Chic House in Bridgeport

Kick back & relax in your home away from home in our modern, quaint, cozy & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & playful artwork, the coach house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Halsted Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Guest favourite

Apartment in Chicago

4.97 out of 5 average rating, 35 reviews

Serene Escape with King Sleep Number Bed, No Fees!

Welcome to our meticulously designed oasis! Relax in luxury on a king-sized Sleep Number bed, refresh in the marbled bathroom with a rain shower, and indulge your culinary passions in the farmhouse-inspired chef's kitchen. Bright, airy, and inviting, our space offers a serene escape. Conveniently located near Belmont CTA Blue Line Station and bus stops, it's the perfect base for your Chicago adventure. Book now for sophistication and comfort!

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Popular amenities for Downtown Chicago Holiday Houses with Outdoor Verandahs

Free parking on premises

Air conditioning

Apartment rentals with a patio

Guest favourite

Apartment in Chicago

4.87 out of 5 average rating, 276 reviews

Historic Old Town Flat - Minutes from Downtown!

Apartment in Logan Square

4.86 out of 5 average rating, 73 reviews

Logan’s Cozy Inn.

Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 20 reviews

Funky Logan Lair

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 30 reviews

Wicker Park Walk-Up Condo

Guest favourite

Apartment in Forest Park

4.99 out of 5 average rating, 96 reviews

Sunny 1 bedroom apartment 1 block from restaurants

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 8 reviews

Lovely Uptown Haven

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Apartment in Illinois Medical District

4.94 out of 5 average rating, 16 reviews

Claremont Cottage Tri-Taylor/UIC/UnitedCenter

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Apartment in Near South Side

4.87 out of 5 average rating, 31 reviews

The Metropolitan Retreat (2BD/2BA)

Holiday House Rentals with a Verandah

Home in Bolingbrook

4.92 out of 5 average rating, 100 reviews

The Sunshine Spot

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 90 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

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Home in Chicago

4.98 out of 5 average rating, 57 reviews

2BD/1 BA with summer patio in quiet Roscoe Village

Guest favourite

Home in Chicago

4.85 out of 5 average rating, 68 reviews

Chicago getaway for two!

Guest favourite

Home in Wrigleyville

5.0 out of 5 average rating, 12 reviews

Cubby Blue home - Wrigley ~Free Parking~

Home in Chinatown

4.78 out of 5 average rating, 41 reviews

Cozy 1BR Apt, mins to DWTN/McCormick, in ChinaTwn

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 73 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Guest favourite

Home in Chicago

5.0 out of 5 average rating, 53 reviews

Architect's Urban Oasis | 4bd/3ba I Luxe

Holiday condos with a patio

Guest favourite

Condo in Chicago

5.0 out of 5 average rating, 102 reviews

Spacious 4 Bedroom Condo

Guest favourite

Condo in Wicker Park

4.96 out of 5 average rating, 112 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Guest favourite

Condo in Chicago

4.82 out of 5 average rating, 311 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Guest favourite

Condo in Chicago

4.98 out of 5 average rating, 108 reviews

Interior designer duplex 2bd 2bath w/ prvt backyd

Guest favourite

Condo in Chicago

4.96 out of 5 average rating, 104 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Condo in Chicago

4.86 out of 5 average rating, 100 reviews

Tri-Taylor/Medical Dist. near West Loop

Condo in Chicago

4.83 out of 5 average rating, 181 reviews

Can't Beat This 2min Walk to Wrigley!

Guest favourite

Condo in Chicago

4.95 out of 5 average rating, 132 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

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