Vacation rentals in Chicago

Apartment in Lincoln Park

A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.

5 out of 5 average rating, 308 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

LocationValueNearby

4.99 out of 5 average rating, 100 reviews

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

Apartment in Chicago

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

FamilyValueBathroom

4.99 out of 5 average rating, 412 reviews

An airy studio bedroom features a spacious bed with white linens and decorative pillows. Large windows allow natural light to fill the room, showcasing a cozy sitting area with a small table and chair. Framed botanical artwork adorns the walls, contributing to a calming ambiance.

Guest suite in Chicago

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

ValueLocationSleep quality

4.96 out of 5 average rating, 242 reviews

An open-concept loft showcases a cozy seating area with a grey couch adorned with yellow and patterned throw pillows. The kitchen, visible in the background, features modern appliances and a bar with two stools. A lofted sleeping area is bordered by a wooden railing.

Loft in Chicago

Lincoln Park Light-Filled Loft

Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows & the conveniences of your own two level suite. A converted store-front, this space is perfect for a couples weekend in Chicago, that friends get-away, or a place to call home for your small family vacation. Walk the neighborhoods & parks, and wonder why you’re not staying longer. We call this our little gem of a find, and are excited to share it with you. We love it, so will you!

FamilyValueBiking

Apartment in Roscoe Village

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.95 out of 5 average rating, 251 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

FamilyValueKitchen

5 out of 5 average rating, 356 reviews

A spacious seating area is defined by a dark upholstered sofa with yellow accent pillows. A modern gold-toned coffee table sits in front, resting on a textured woven rug. Art pieces adorn the walls, contributing to the room's thoughtful design.

Apartment in Lake View

An elegant Chicago Northside Getaway

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

ValueLocationGetting around

4.96 out of 5 average rating, 151 reviews

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Condo in Avondale

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

LocationFamilyCheckout

4.99 out of 5 average rating, 139 reviews

A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.

Loft in South Side

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

FamilyValueWalkability

Superhost

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Dunning

4.92 out of 5 average rating, 169 reviews

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

FamilyLocationQuiet

4.96 out of 5 average rating, 279 reviews

A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.

Home in Wicker Park

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).

FamilyLocationIndoor spaces

4.99 out of 5 average rating, 146 reviews

Home in Wrigleyville

Whole apartment! 2 Bed/2 bath steps from Wrigley!!

Newly rehabbed urban nest among the tree-lined streets of beautiful East Lakeview. Literally 60 seconds to Wrigley Field, close to bars, restaurants, El train/busses, and lakefront. You’ll have loads of space in this 2 bed, 2 bath, plus office and large laundry room with FREE full size W/D. Free parking passes! Owner lives near by and is happy to help with anything you need to make your trip the best it can be. Flexible check in/out times upon request.

FamilyValueIndoor spaces

4.98 out of 5 average rating, 120 reviews

A stately Victorian house is surrounded by a landscaped garden featuring lush greenery and colorful plants. The front porch is framed by pillars and features multiple seating areas. A red front door adds a bold contrast to the dark exterior of the home.

Home in Chicago

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

ValueFamilyAccess

Popular amenities for Chicago vacation rentals

Self check-in

Monthly stays

Lake access

Free parking on premises

Gym

What Airbnb hosts recommend seeing in Chicago

Find unforgettable activities and unique points of interest near you. Our hosts share their favorite things to do and must-visit places to see in Chicago.

Millennium Park

Urban oasis featuring iconic public art, lush gardens, and free cultural events

Summarized by AI

At Millennium Park you can photograph your reflection at Cloud Gate (“the Bean”), cool off in Crown Fountain, wander the Lurie Garden, and explore public art, Wrigley Square, and the pine forest along the walking paths. Catch free concerts, movies, festivals, and classical performances at the Frank Gehry–designed Jay Pritzker Pavilion, or join free outdoor workouts like tai chi, yoga, Pilates, and Zumba on summer Saturdays. In winter, skate the ribbon; in warmer months, enjoy rock climbing and kid-friendly play areas, with Maggie Daley Park just across the pedestrian bridge.

Mentioned by 1,649 local hosts

Wrigley Field

Historic baseball stadium featuring ivy-covered walls, a hand-turned scoreboard, and lively surrounding bars

Summarized by AI

At Wrigley Field you can catch a Chicago Cubs game, eat a classic Chicago hot dog or a memorable sausage from Hot Doug’s, and take in the ivy-covered brick walls, iconic red marquee, and manually operated scoreboard. Join an in-season or behind-the-scenes tour to visit the press box, locker rooms, batting cages, dugouts, and even up by the scoreboard. In summer, come for occasional concerts, and in colder months check out the Christmas Market and Winter Wonderland. Afterward, linger in Wrigleyville’s bars and Gallagher Way to keep the game-day energy going.

Mentioned by 2,185 local hosts

United Center

Premier sports and entertainment venue home to the Bulls, Blackhawks, and major concerts

Summarized by AI

Step into Chicago’s largest indoor arena to watch the Chicago Bulls and Chicago Blackhawks play on their home court and ice, or catch major concerts, Disney on Ice, the circus, and other large-scale shows. Inside, look up at the 58 championship banners and visit the 12-foot bronze statue of Michael Castro for a photo with #23. The United Center also hosts big events like political conventions, college tournaments, and world-famous tours. After your event, you can grab a Cheezborger at nearby Billy Goat Tavern.

Mentioned by 345 local hosts

Navy Pier

Vibrant waterfront destination with attractions, dining, and stunning views of Lake Michigan

Summarized by AI

At Navy Pier you can ride the 150-foot Centennial Ferris wheel, historic carousel, and other carnival rides, explore the Chicago Children’s Museum and indoor glass maze, see a show at Chicago Shakespeare Theater, or catch a film at the IMAX theater. Stroll through the Crystal Gardens indoor botanical garden, browse shops, and try multiple Chicago restaurants, bars, dessert spots, and the large rooftop bar at the end of the pier. In summer, enjoy lake cruises, sightseeing and dinner boats, live bands, and fireworks every Wednesday and Saturday night. Seasonal events like Winter WonderFest add indoor rides, giant slides, ice skating, and holiday décor for families.

Mentioned by 2,027 local hosts

Soldier Field

Historic stadium hosting Chicago Bears games, concerts, and major events

Summarized by AI

Catch a Chicago Bears NFL game or a Chicago Fire soccer match at Soldier Field, where the energy from passionate fans, team colors, and loud chants fills this open-air stadium. Enjoy major concerts and festivals here too—everyone from Beyoncé to the Rolling Stones has performed in this iconic venue. Built in 1924 and later modernized, it combines historic colonnades with views of Lake Michigan and the skyline. Even on non-game days, it’s a landmark for soaking up Chicago sports history and taking memorable photos.

Mentioned by 336 local hosts

Humboldt (Alexander Von) Park

Expansive park with lagoons, sports fields, a boathouse, and cultural attractions

Summarized by AI

At Humboldt Park you can walk or run miles of trails, relax on the grass, or set up a picnic by the lagoons, inland beach, or waterfall. Rent giant swan paddle boats at the historic boathouse, play tennis, soccer, or baseball, let kids loose on multiple playgrounds, or watch birds and other wildlife in the bird sanctuary and prairie-style gardens. In summer, look for Puerto Rican food trucks around the park, then head to nearby Division Street for jibaritos and other Puerto Rican dishes.

Mentioned by 299 local hosts

Private Chicago vacation rentals

4.92 out of 5 average rating, 181 reviews

The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.

Apartment in Wicker Park

Stylish 2BR stunner w/ unbeatable location

LocationValueLong stay

4.86 out of 5 average rating, 285 reviews

An airy open living space features polished concrete floors and high wooden ceilings with exposed beams. Large windows illuminate the room, which includes a dining table with white chairs, a cozy seating area with green and neutral furnishings, and a decorative plant in the corner.

Apartment in West Loop

Chic Penthouse Corner 3BR Loft In Fulton Market |

LocationFamilyCheckout

4.97 out of 5 average rating, 131 reviews

The exterior of a historic building showcases large glass windows framed by green trim. Natural light streams into the space, illuminating various items displayed inside. The backdrop features a view of a nearby architectural structure, adding visual interest to the streetscape.

Condo in Chicago

Private Lincoln Park Condo with 2 Parking Spots

LocationFamilyGetting around

Guesthouse in Little Italy

A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.

4.99 out of 5 average rating, 927 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

LocationFamilyDecor

5 out of 5 average rating, 100 reviews

A charming three-story building is framed by lush greenery and blooming daffodils at its base. The stone façade features decorative columns and a welcoming front entrance, complemented by a wrought iron fence surrounding the landscaped front yard.

Home in Wrigleyville

WrigleyRoost <5 min to Cubs/train/lake!

FamilyLocationBathroom

Apartment in Near North Side

The bedroom features two twin-size beds, each dressed in crisp white linens. A table lamp provides soft illumination between the beds, which are flanked by framed abstract artwork on the walls. Large windows allow natural light to fill the space.

4.84 out of 5 average rating, 188 reviews

Kasa | Walk Magnificent Mile | River North

ValueFamilyLaundry

4.96 out of 5 average rating, 533 reviews

A stylish living area features a white sofa with bright yellow cushions, set against exposed brick walls. A flat-screen TV is positioned above a modern fireplace. A wooden staircase leads to the upper level, while a kitchen bar with dark countertops is visible on the left.

Condo in Lincoln Park

Unique Lincoln Park Duplex Apt

FamilyLocationLayout

4.87 out of 5 average rating, 110 reviews

A modern living area is illuminated by natural light from large floor-to-ceiling windows. A comfortable gray sofa sits against one wall, accompanied by a coffee table. The open kitchen features a sleek marble countertop and stainless steel refrigerator, with minimalistic decor enhancing the ambiance.

Apartment in River North

River North | Private Balcony With In&Out Parking

FamilyLocationTV

Vacation rentals with jacuzzis in Chicago

4.88 out of 5 average rating, 371 reviews

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

Guesthouse in Chicago

Private Coach house near Lincoln Square!

ValueFamilyHospitality

4.85 out of 5 average rating, 333 reviews

A spacious living area features a blend of warm wall colors and modern decor. Comfortable seating includes a light-colored sofa and a wooden chair. A fireplace is highlighted on one wall, accompanied by a ceiling fan and natural light from large windows.

Home in River West

Lux Urban 3BR/3BA Duplex + Parking!

ValueLocationAmenities

Condo in Ukrainian Village

The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.

4.98 out of 5 average rating, 110 reviews

Ukrainian Village 3BR/3BA • Jet Tub, Private Patio

FamilyLocationTV

4.95 out of 5 average rating, 164 reviews

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

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

LocationValueSleep quality

4.96 out of 5 average rating, 294 reviews

A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.

Loft in Wicker Park

Tea Studio in Wicker Park Spring Factory

FamilyLocationLong stay

4.97 out of 5 average rating, 172 reviews

An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.

Condo in West Town

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

FamilyValueCheck-in

4.86 out of 5 average rating, 174 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

FamilyLocationHot tub

Apartment in Humboldt Park

An open and spacious living area features a white sectional sofa and unique cow print coffee table. The dining space is equipped with round chairs, and a modern kitchen is visible in the background. Light streams through frosted glass block windows, enhancing the airy atmosphere.

4.86 out of 5 average rating, 519 reviews

Checkerboard Studio, Private Outdoor Hot Tub, Yard

ValueLocationQuiet

Pet-friendly vacation rentals in Chicago

Apartment in Noble Square

A modern living area is shown featuring a light-colored sectional sofa and a wall-mounted television. Natural light enters through large windows, and a small indoor plant adds a touch of greenery. A low coffee table sits in front of the seating area, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 120 reviews

Wicker Park Walk-Up Condo

FamilyLocationPets

4.98 out of 5 average rating, 123 reviews

A spacious kitchen features sleek black countertops and a large central island. Stainless steel appliances include a refrigerator and a gas range. Natural light enters through the windows, illuminating decorative plants and kitchen essentials arranged on shelves.

Home in North Side

Flat in Lincoln Park 2-Flat Central to Everything

FamilyLocationNearby

4.91 out of 5 average rating, 404 reviews

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 Lake View

Private 3rd Floor Apartment

LocationFamilyHospitality

4.98 out of 5 average rating, 241 reviews

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

Condo in Lake View

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

FamilyValueWifi

4.97 out of 5 average rating, 478 reviews

A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.

Condo in Chicago

Lincoln Square Gem!

LocationValueParks

Superhost

A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.

Loft in Brookfield

4.89 out of 5 average rating, 163 reviews

1920s fully updated unique open artist loft space

ValueFamilyLayout

4.83 out of 5 average rating, 105 reviews

Home in Chicago

Private Roofdeck! Location! Parking! Amazing home!

ValueLocationComfort