Vacation rentals with a patio in Old Town, Chicago

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Top-rated patio rentals in Old Town, Chicago

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Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 70 reviews

English garden apt. in the heart of Lincoln Park

Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

Sep 14 – 21

G$41,693 GYD per night

Guest favorite

Apartment in Wicker Park

4.96 out of 5 average rating, 101 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.

Aug 23 – 30

G$48,889 GYD per night

Superhost

Apartment in Chicago

4.88 out of 5 average rating, 64 reviews

Family-Friendly 2BD/2BA in the heart of Old Town

Getaway to this authentic Old Town apartment! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Privacy is hard to beat in this beautiful courtyard! - Luxurious interior design - Master en-suite w/ all the bells/whistles! - Extremely Fast WiFi - Pillow-top Bamboo mattresses - Charming neighborhood - 5-10 minute walk from red line (CTA L) We look forward to hosting you!

Jun 24 – Jul 1

G$87,564 GYD per night

Guest favorite

Condo in Chicago

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!

Jan 8 – 15

G$105,167 GYD per night

Superhost

Apartment in Lincoln Park

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.

Jan 21 – 28

G$35,400 GYD per night

Guest favorite

Condo in West Town

5.0 out of 5 average rating, 100 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Feb 16 – 23

G$80,968 GYD per night

Guest favorite

Apartment in Lincoln Park

4.83 out of 5 average rating, 211 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!

Nov 18 – 25

G$32,682 GYD per night

Guest favorite

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).

Aug 3 – 10

G$105,205 GYD per night

Guest favorite

Condo in Lincoln Park

4.96 out of 5 average rating, 102 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Just steps from the lively center of Chicago's Lincoln Park and poised above the quiet, tree-lined streets of the coveted Arlington-Deming neighborhood, this residence on the top floor of a three-story walkup is the perfect for families that want to be close to it all! Lake Michigan, Lincoln Park Zoo, multiple parks, transportation, dining, nightlife, and more. We provide one daily parking permit per night of your stay so you can access free street parking.

Sep 1 – 8

G$72,571 GYD per night

Guest favorite

Apartment in Lincoln Park

4.94 out of 5 average rating, 17 reviews

Beautiful Lincoln’s Guestplace

Enjoy a stylish experience at this brand new apartment in the heart of Lincoln Park and right to the Lake with wonderful, clean and safe beach! This gorgeous, just renovated place has a private entrance, 1 bedrooms and luxury kitchen with a shared front yard. we're surrounded by the best shops and restaurants in CHI. I provide all the essentials to make your stay comfortable. Toilet paper, soaps, shampoos, towels, linens and Nespresso coffee!

Jan 11 – 18

G$70,581 GYD per night

Guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 35 reviews

Stylish 2 BDR Coach House Steps From The Lake

Welcome to our stylish coach house located in the heart of the city, just moments away from the picturesque shores of Lake Michigan and the charming Old Town neighborhood. With two bedrooms, one bathroom, and an inviting ambiance, this is the perfect retreat for your stay in our vibrant city. Very close to upscale shopping, in a very central location. Enjoy two full bedrooms and a full bath. You will be awed at the interior design.

Jun 12 – 19

G$72,586 GYD per night

Guest favorite

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.

Feb 7 – 14

G$25,873 GYD per night