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Vacation rentals with a patio in Chicago Loop

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Top-rated patio rentals in Chicago Loop

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Apartment in Chicago

4.86 out of 5 average rating, 29 reviews

The Metropolitan Retreat (2BD/2BA)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Guesthouse in Chicago

4.92 out of 5 average rating, 13 reviews

Private Coach House / Easy Commute

Located in the vibrant neighborhood of Logan Square, known for its hip atmosphere, tree-lined streets, and diverse dining scene, this private apartment is a perfect home away from home for your visit to the Windy City. Whether you're a culinary enthusiast or just looking to whip up a quick snack, you'll find everything for your cooking needs. Convenient public transportation, you can access all that Chicago has to offer. 10 mins walk to the train to get to either downtown Chicago or O’Hare.

Apartment in Oak Park

4.92 out of 5 average rating, 106 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!

Apartment in West Town

5.0 out of 5 average rating, 28 reviews

Wicker Park Walk-Up Condo

Enjoy the best of what Chicago has to offer. Located in the West Town/Wicker Park Neighborhood, steps away from the exciting Division St. and Milwaukee Ave. lined with great neighborhood bars, restaurants, boutiques, etc. Centrally located steps from public transit (The "L" Train/Bus), the expressway, Goose Island, Lincoln Park, & More. Experience one of Chicago's best and most interesting neighborhoods! This apartment is fully furnished with modern touches, a private rear deck & front patio.

Condo in Little Italy

4.96 out of 5 average rating, 121 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.

Apartment in Roscoe Village

4.91 out of 5 average rating, 34 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

Apartment in Edgewater

4.8 out of 5 average rating, 5 reviews

Lovely Lake Side Apartment

Enjoy a stylish experience at this centrally-located place. My studio apartment is right off of Lake Shore Drive. Across the street from Hollywood beach, a 4 minute walk. The 147 bus stop is right outside the apartment, which gets you downtown in 30 mins and the red line is a short 5-7 minute walk. The apartment is on the 12th floor with an amazing view of the city. The space is equipped with coffee station, records, books, art, and a great pantry of spices for those that enjoy cooking.

Condo in West Loop

4.96 out of 5 average rating, 178 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!

Apartment in Chicago

4.86 out of 5 average rating, 188 reviews

Perfect Lincoln Park Retreat - Walk to Depaul!

This perfectly located 2 BD/2 BA unit is waiting for you to call it home for your trip to gorgeous Lincoln Park! Make yourself comfortable in the sleek and modern interior of this newly renovated garden unit. Enjoy all of the comforts of home, as well as some cool features you don't see every day– such as LED-lit mirrors in both bathrooms! Walk to famous attractions like the historic Kingston Mines blues bar and the Lincoln Park Zoo, as well as the DePaul campus & 'El' train stop.

Apartment in Lincoln Park

4.83 out of 5 average rating, 212 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!

Home in Chicago

4.96 out of 5 average rating, 202 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).

Apartment in Cicero

4.98 out of 5 average rating, 204 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

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Popular amenities for Chicago Loop patio rentals

Free parking on premises

Air conditioning

Apartment rentals with a patio

Apartment in Wicker Park

4.96 out of 5 average rating, 102 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Apartment in Logan Square

4.98 out of 5 average rating, 64 reviews

Colorful & Peaceful Boho-Chic Unit in Logan Square

Apartment in Forest Park

4.99 out of 5 average rating, 93 reviews

Sunny 1 bedroom apartment 1 block from restaurants

Apartment in Chicago

4.97 out of 5 average rating, 35 reviews

Fulton House #1 - Studio Only

Apartment in Hermosa

4.93 out of 5 average rating, 40 reviews

Cozy 2BR, Own Entrance, Gated Free Parking Spot

Apartment in Logan Square

5.0 out of 5 average rating, 10 reviews

Paradise on the Boulevard!

Apartment in Chicago

5.0 out of 5 average rating, 5 reviews

Fantastic West Loop 2 bedroom

Apartment in Oak Park

4.98 out of 5 average rating, 66 reviews

Cheerful Oak Park Apartment

House rentals with a patio

Home in Chicago

4.91 out of 5 average rating, 89 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Home in Jefferson Park

4.88 out of 5 average rating, 64 reviews

Chicago getaway for two!

Home in Chicago

5.0 out of 5 average rating, 12 reviews

Cubby Blue home - Wrigley ~Free Parking~

Home in Chicago

4.95 out of 5 average rating, 19 reviews

Spacius unit in historic gem

Home in Chicago

4.93 out of 5 average rating, 71 reviews

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

Home in Chicago

5.0 out of 5 average rating, 31 reviews

NEW! 3BR/2.5B Duplex in Noble Sq

Home in Lake View

4.98 out of 5 average rating, 56 reviews

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

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

Condo rentals with a patio

Condo in Chicago

5.0 out of 5 average rating, 100 reviews

Spacious 4 Bedroom Condo

Condo in Chicago

4.95 out of 5 average rating, 111 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Condo in Lake View

4.98 out of 5 average rating, 105 reviews

Interior designer duplex 2bd 2bath w/ prvt office

Condo in Chicago

4.96 out of 5 average rating, 102 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Condo in Wrigleyville

4.83 out of 5 average rating, 178 reviews

Can't Beat This 2min Walk to Wrigley!

Condo in Chicago

4.82 out of 5 average rating, 188 reviews

Chicago River West 4 Bedroom / 3 Bathroom

Condo in Chicago

4.95 out of 5 average rating, 129 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Condo in Wicker Park

4.82 out of 5 average rating, 310 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Quick stats about vacation rentals with a patio in Chicago Loop

Total rentals
230 properties
Rentals with a pool
170 properties have a pool
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
7.3K reviews
Nightly prices starting at
R739 ZAR before taxes and fees

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