Chicago vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chicago

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Rental unit in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
A vintage lovers dream! This loft was designed with a love for the past. Starting in the kitchen, you’ll see the beautiful zinc alloy countertops are complemented by gorgeous antique mirror backsplashes. You’ll have access to a stovetop, microwave, coffeemaker, as well as basic tools and kitchen supplies. There is a lovely throwback SMEG 50’s refrigerator and the shelves are all reclaimed wood. This antique lumber detail can be found throughout the loft, from the floors all the way to the night stands. The bathroom door may be recycled wood and the mirrors antique, but the shower fixtures are all Grohe. There is also a hair-dryer as well as complimentary toiletries and clean towels for your use. At the end of the day, you can sit on our funky wicker swing chair and think of all the chic guests who may have used the closet doors that were brought in from NY’s Plaza hotel! You’ll surely have the sweetest of dreams when you go to sleep on the memory foam mattress following a quick binge using the complimentary netflix. Additional amenities include self-controlled A/C and closet space with hangers, an iron and ironing board. This loft is very well kept, professionally cleaned and sanitized after each and every use. When booking this studio you will have full and private access to the entire apartment. There is a shared deck and lounge area you are welcome to use. For your convenience, we have arranged luggage drop-off/storage before and after your stay at the restaurant right down stairs - do note this is a courtesy. Our check-in and check-out process is automatic and seamless, once you book you will receive a private entry code ahead of your stay. Check-in any time after three pm as late as you'd like, check-out on or before 11 am. Due to our cleaning schedule we cannot accommodate early check-ins or late check-outs. The provided free parking spot is located a block away from the Airbnb unit Someone who’s offsite will be available as needed Set between South Old Irving and Kilbourn parks, the studio is located in one of Chicago's most historical neighborhoods. Sample the craft beer taverns and cocktail bars lining North Milwaukee Avenue. Wrigley Field is about 10 minutes away by car. The quickest and most inexpensive way to get around is via Uber or Lyft. If reaching the apartment by vehicle, there is free street parking in the surrounding neighborhood (please follow the local laws and signs). Public Transportation guide to the apartment: From Chicago O'Hare Int'l Airport: Take the Blue Train line to Irving Park Station and then transfer to the CTA #53 Milwaukee bus line to reach the apartment. You can also take the Blue Train line to Jefferson Park Station and then transfer to the CTA #56 Milwaukee bus line to reach the apartment. To/From Downtown Chicago: The CTA #56 Milwaukee bus is a very convenient and direct way to reach the Downtown Chicago Loop with a station just below the apartment. To/From Wrigley Field: Easily catch a game via the 77 or 152 buses, with a station just close by the apartment. Train and bus maps can be found and downloaded here: https://www.transitchicago.com/maps/ Please note that the provided free parking spot is located a block away from the Airbnb unit.
$60 per night
PLUS
Condo in Little Italy
Private hot tub and king bed suite
Welcome to this historic yet chic 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 entertainment, museums, shopping, food and nightlife the city has to offer. At the end of your day, enjoy a relaxing soak in your private outdoor patio hot tub before sinking in to your Tempur-Pedic king bed for a restful night's sleep.
$116 per night
SUPERHOST
Condo in Logan Square
Bucktown high-end condo w/outdoor patio /APT 1
This freshly remodeled condo decorated in the Japandi style is set in the trendy yet peaceful neighborhood of Bucktown - a perfect base for exploring Chicago. A short walking distance to 2 Blue line CTA stops (Western and Damen), it is surrounded by quaint neighborhood bars, restaurants, and coffee shops as well as grocery stores and trendy shopping.
$102 per night
SUPERHOST

Stay near Chicago's top sights

Photo of Millennium Park
Millennium Park1,244 locals recommend
Photo of Navy Pier
Navy Pier927 locals recommend
Photo of Wrigley Field
Wrigley Field1,004 locals recommend
Photo of Lincoln Park
Lincoln Park175 locals recommend
Photo of United Center
United Center199 locals recommend
Photo of Magnificent Mile
Magnificent Mile598 locals recommend

Downtown Chicago vacation rentals

Rental unit in West Town
Cute Designer Touch Minimal Loft,Blue Line
$51 per night
Private room in Lake View
Queen Bed with Private Bathroom in Boystown
$34 per night
SUPERHOST
Guesthouse in Wicker Park
Unwind in the Bath at a Hip, Historic Coach House
$91 per night
PLUS
Rental unit in Wicker Park
1-Bedroom Unit with Free Garage Parking
$99 per night
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
$87 per night
Private room in West Town
Stylish & Ample 1PBR TWO Miles From Downtown
$43 per night
SUPERHOST
Rental unit in Logan Square
Lofted 2nd Floor Apartment with Spiral Staircase
$60 per night
Rental unit in Lake View
Uplifting Studio Apartment in Belmont
$44 per night
Condo in Wicker Park
Modern Izakaya Studio in Wicker Park
$126 per night
SUPERHOST
Rental unit in Near North Side
52nd Floor MagMile Penthouse Views Fireplace Pool
$173 per night
SUPERHOST
Rental unit in Lake View
Well-furnished 1BR Home in Lakeview w/ Free Wi-Fi
$57 per night
Rental unit in Lake View
Lux 1BR/1BA Apartment in Belmont
$50 per night

Chicago summer vacation rentals

Rental unit in Humboldt Park
(No Cleaning fees) Cozy North Side Oasis
$78 per night
Rental unit in Lake View
Beautiful Belmont 1BR Apt w/ In-Unit Washer/Dryer
$46 per night
Rental unit in Irving Park
Modern Chicago Loft with a Complimentary Garage Spot
$60 per night
PLUS
Rental unit in Uptown
Vibrant studio at Uptown by Red Line (02)
$49 per night
SUPERHOST
Private room in West Town
Stylish & Bright 1PBR TWO Miles From Downtown
$43 per night
SUPERHOST
Rental unit in Little Italy
UIC / Little Italy - Adorable 2 Bed 1 Bath Apt.
$98 per night
Rental unit in Lake View
Studio Alluring & Secure Apt with Wi-Fi Included!
$48 per night
Rental unit in Magnificent Mile
Steps to MI Ave Shops | View, Beach, Gym | Zencity
$83 per night
Private room in The Loop
Downtown/Lake/Soldier Field Paradise Haven
$109 per night
SUPERHOST
Rental unit in Lake View
10% Winter Promo! Comfy Studio Close to Boystown
$45 per night
Private room in Chicago
New Queen bed near Downtown Chicago Chinatown
$30 per night
Rental unit in Lake View
Splendid 1BR Apt in Lakeview
$46 per night

Chicago holiday vacation rentals

Private room in West Town
Stylish & Bright 1PBR 2 Miles From Downtown
$43 per night
SUPERHOST
Rental unit in Lake View
Best Value 1-Bedroom Chicago Apartment!
$54 per night
Private room in McKinley Park
Downtown Chicago 8 minutes away New Queen Bed
$34 per night
Rental unit in Uptown
Stylish 1 bdr close Downtown|Wrigley|Andersonville
$47 per night
SUPERHOST
Rental unit in Portage Park
Mesmerizing Studio with a free Parking Spot!
$51 per night
SUPERHOST
Rental unit in Lake View
Adorable Studio Apartment in Lakeview
$47 per night
Private room in Bridgeport
The Modern Bedroom in Bridgeport Chicago
$28 per night
Rental unit in Uptown
Modern studio at Uptown by Red Line,Aragon,Riviera
$49 per night
SUPERHOST
Private room in Bridgeport
Luxury Stay near Downtown Chicago New Queen bed
$35 per night
Rental unit in Lake View
1BR Attractive Rental Unit in Chicago
$46 per night
Condo in Oak Park
Lavish Executive Suite w/free prkng near DT Oak PK
$81 per night
SUPERHOST
Rental unit in Irving Park
Cozy and Stylish Studio with Free Parking in Irving Park
$52 per night
PLUS

Your guide to Chicago

All About Chicago

Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.

You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.


When is the best time to stay in a vacation rental in Chicago?

Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.


What are the top things to do in Chicago?

The Art Institute of Chicago

The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.

Willis Tower

The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.

Millennium Park

Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.

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