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Vacation rentals in Chicago

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chicago vacation rentals

Self check-in
Monthly stays
Lake access
Free parking on premises
Gym

Stay near Chicago's top sights

O'Hare International Airport14 locals recommend
Wrigley Field158 locals recommend
United Center50 locals recommend
Millennium Park213 locals recommend
Navy Pier274 locals recommend
University of Chicago14 locals recommend

Chicago fishing vacation rentals

Top guest favorite
A spacious living area features a large gray sectional sofa adorned with yellow accent pillows. A round wooden coffee table sits in front, with decorative items arranged on it. Two framed artworks are displayed on the wall beside a tall green plant, contributing to a modern aesthetic.
Apartment in Near West Side
4.99 out of 5 average rating, 143 reviews

KING bed FREE P-Spot EV EZZY Accessible NO stairs

Top guest favorite
A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.
Apartment in Evanston
4.97 out of 5 average rating, 504 reviews

Charming, Sunny Apartment with Backyard Garden

Guest favorite
A cozy living area features comfortable seating with a dark blue sofa, two armchairs, and a wooden coffee table. Natural light streams through large windows adorned with decorative frames. A small decorative tree and artwork add warmth to the space, complemented by a soft area rug.
Home in Lincoln Park
4.85 out of 5 average rating, 173 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Top guest favorite
A spacious dining area features a large table surrounded by six chairs. Natural light is provided by two windows with sheer curtains. A unique light fixture hangs above, and a vase with flowers is centered on the table, contributing to the room's welcoming ambiance.
Home in Uptown
4.9 out of 5 average rating, 372 reviews

Private 3rd Floor Apartment

Top guest favorite
A comfortable living area is presented, featuring a brown sofa, light teal chairs, and a white coffee table. Soft lighting is provided by two lamps on either side of a teal accent table. Natural light filters through the window shutters, enhancing the cozy ambiance.
Apartment in Lincoln Park
4.98 out of 5 average rating, 376 reviews

Lincoln Pk-parking-wifi-King bd-crib-kid friendly

Top guest favorite
A well-maintained gray exterior with white trim is presented. Surrounded by a wooden fence, the yard features a grassy area and is shaded by trees. A sunny sky with scattered clouds adds to the inviting ambiance of the outdoor space.
Home in Evanston
5 out of 5 average rating, 109 reviews

Larimer Park Carriage House

Guest favorite
The master bedroom features a spacious bed with a tufted headboard and soft, neutral bedding. Two nightstands with lamps are on either side, and a television is mounted on the wall. Natural light filters through the wooden blinds, enhancing the warm wooden floors.
Apartment in Old Town
4.93 out of 5 average rating, 209 reviews

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Superhost
An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.
Apartment in East Rogers Park
4.89 out of 5 average rating, 179 reviews

Executive Apartment on Lake Michigan with parking

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Chicago house rentals

Top guest favorite
A collage of the Mini Golf House showcases the vibrant mini golf area, a cozy lounge with arcade games, a comfortable sleeping space, and a living area featuring a large TV. The layout highlights inviting spaces designed for entertainment and relaxation.
Home in Whiting
4.95 out of 5 average rating, 110 reviews

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

Top guest favorite
Home in Lincoln Park
4.98 out of 5 average rating, 108 reviews

Flat in Lincoln Park 2-Flat Central to Everything

Guest favorite
An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.
Home in Bridgeport
4.96 out of 5 average rating, 124 reviews

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

Top guest favorite
A welcoming living area is presented with a mix of plush seating, including a white chair and a vibrant orange sofa. A wooden shelving unit displays decorative items and books. Soft lighting enhances the wooden floor, while light streams through large windows dressed with sheer coverings.
Home in Lincoln Square
4.98 out of 5 average rating, 117 reviews

Entire first floor in Lincoln Square!

Top guest favorite
The exterior of a restored Victorian house is presented, featuring a striking red front door and large windows that invite natural light. A welcoming porch is adorned with seating, surrounded by meticulously landscaped greenery and plants, creating an engaging atmosphere.
Home in East Rogers Park
4.98 out of 5 average rating, 103 reviews

Victorian House in Heart of Rogers Park

Guest favorite
A modern living area features a dark leather sofa adorned with blue and cream cushions. A stylish coffee table with geometric design sits atop a decorative area rug. A large black and white photograph of a city skyline is displayed on the wall, complemented by a floor lamp and a side table.
Home in Pilsen Historic District
4.95 out of 5 average rating, 402 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

Guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago
4.87 out of 5 average rating, 143 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Guest favorite
A cozy living area is depicted with a plush sofa positioned opposite a wall-mounted television. Natural light streams through large windows, illuminating the space. A coffee table with a candle adds a touch of warmth to the setup, while the walls feature a soft green hue.
Home in Chicago Ridge
4.91 out of 5 average rating, 147 reviews

Quiet cul-de-sac with huge fenced in backyard

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Chicago apartment rentals

Top guest favorite
A spacious kitchen area features a large wooden island with seating at the edge. Cabinets with glass doors store dishware, while a white refrigerator stands against the wall. Sunlight streams through the two large windows, illuminating the warm wooden flooring.
Apartment in Ukrainian Village
4.91 out of 5 average rating, 451 reviews

iKlektik House Chicago / Cardinal

Guest favorite
A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.
Apartment in Hyde Park
4.93 out of 5 average rating, 116 reviews

Spacious 1BR Garden Apt & Parking

Top guest favorite
The living area features exposed brick walls, contributing to a vintage feel. A cozy sofa is positioned next to a wooden coffee table, while a television is mounted on a rustic console. Natural light enters through two windows, covered with light blinds.
Apartment in Logan Square
4.96 out of 5 average rating, 101 reviews

Bucktown Brick Cottage Apartment

Superhost
A dining area features a wooden table with seating for four, positioned against a textured brick wall. Two windows allow natural light to fill the space, with sheer curtains gently framing them. A vibrant green plant and neon 'CHICAGO' sign add character to the room.
Apartment in Wicker Park
4.93 out of 5 average rating, 111 reviews

怐Central怑- Eclectic Fun 1BR APT in Wicker Park

Top guest favorite
An inviting living space features large windows allowing natural light, framed by exposed brick walls. A round dining table is surrounded by modern chairs, while a comfortable sectional sofa is positioned near a cozy fireplace, enhancing the warm ambience. Stylish decor elements add character to the room.
Apartment in Lake View
4.97 out of 5 average rating, 220 reviews

Modern vintage chic steps from Wrigley Field!

Guest favorite
A spacious living area is highlighted by large windows that provide ample natural light. A contemporary sofa faces a round black table, complemented by a vibrant red area rug. A striking mural adorns the wall behind the seating, adding a bold artistic touch to the space.
Apartment in The Loop
4.89 out of 5 average rating, 244 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Guest favorite
A spacious living area features a light-colored sofa and a dark wood coffee table, surrounded by large windows that allow ample natural light. Decorative plants are placed around the room, and a brick fireplace adds a focal point, complemented by framed artwork on the walls.
Apartment in Albany Park
4.9 out of 5 average rating, 183 reviews

Huge Pet Friendly East Albany Park Apartment

Top guest favorite
A cozy seating area features a round table surrounded by two chairs. A potted plant is positioned nearby, contributing to the fresh atmosphere. A glass coffee table rests on a patterned rug, while a comfortable gray sofa with assorted cushions is present against the wall.
Apartment in Ukrainian Village
4.98 out of 5 average rating, 286 reviews

Ukrainian Village Garden Retreat

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Quick stats about vacation rentals in Chicago

  • Total rentals

    11K properties

  • Total number of reviews

    544K reviews

  • Family-friendly rentals

    5.3K properties are a good fit for families

  • Pet-friendly rentals

    3.6K properties allow pets

  • Rentals with a pool

    1.2K properties have a pool

  • Rentals with dedicated workspaces

    6.8K properties have a dedicated workspace

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, thereā€™s a unique aura found in each.

Youā€™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.

The best time to stay in a vacation rental in Chicago

Chicagoā€™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 itā€™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 thereā€™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.

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 cityā€™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 thatā€™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. Itā€™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 ā€œThe Bean.ā€ 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.

Frequently Asked Questions

  • How is the weather in Chicago?

    Chicago experiences a wide range of weather, from hot summers that can reach 95Ā°F (35Ā°C) to chilly winters that can drop to 20Ā°F (-6Ā°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.

  • What are some of the best things to do in Chicago?

    In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.

  • What is the best time of year to visit Chicago?

    Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.

  • What are the best places to stay in Chicago?

    Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.

  • What are the best places to visit in Chicago?

    Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.

  • What are some hiking trails in Chicago?

    While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.

  • What are some family activities to do in Chicago?

    Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.

  • What are some of the best day trip ideas in Chicago?

    For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.

  • What types of vacation rentals are available in Chicago?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chicago. From over 6,420 apartment rentals, over 1,060 condo rentals to over 2,010 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Chicago?

    Yes! Work meets play with ease at over 6,880 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

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