Vacation rentals in Chicago

Book unique homes, vacation rentals, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

O'Hare International Airport122 locals recommend
Wrigley Field1,004 locals recommend
Boystown92 locals recommend
Logan Square174 locals recommend
United Center200 locals recommend
Millennium Park1,243 locals recommend

Chicago fishing vacation rentals

Top guest favorite
An inviting living area showcases a light-colored sectional sofa paired with a matching ottoman. A dark coffee table sits nearby, and a warm area rug lies underfoot. A bookshelf filled with books lines the wall, while soft lighting highlights the natural warmth of the wood flooring.
Home in Lake View
4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars6 months ago
Lovely place in a good location.
Guest favorite
A cozy living area is highlighted by a red accent wall and brick details. A comfortable blue sofa faces a mounted television, with a striped chair nearby. A mirror and decorative plant are positioned against a stylish cabinet, complementing the space's inviting layout.
Apartment in Lake View
4.83 out of 5 average rating, 442 reviews

Lakeview Charmer -with parking!

LisaRating, 5 stars3 weeks ago
Great location! Felt safe and easy to get around. Close to the Vic Theater and the El. The space was very comfortable for 3 of us. Once we figured out the codes/keys, it was easy enough. I would definitely stay again. Cathy is super easy to talk to and very responsive. Thank you, Cathy!
Superhost
A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.
Apartment in Evanston
4.83 out of 5 average rating, 178 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

SkylarRating, 5 stars3 weeks ago
Craig was extremely nice and accommodating when it came to my birthday weekend. He responds quickly to all questions asked and makes sure we’re comfortable at all times. This home was clean, accurately described, and had the perfect “home feeling”. Overall, when visiting the area I will be booking here again !
Top guest favorite
A cozy living room features a warm fireplace with a flat-screen TV mounted above. Comfortable leather chairs and a plush sofa surround a coffee table, while large windows allow natural light to fill the space. Potted plants add a touch of greenery.
Bungalow in Lake View
4.95 out of 5 average rating, 113 reviews

Chicago Bootlegger House Sleeps 10-20

MikeRating, 5 starstoday
This location exceeded our expectations. The location was great. Restaurants, bars, groceries, etc were really close by. We weren’t able to take advantage of the location as much as we wanted only due to the cold, windy weather. We would have done more on the lakefront and on their rooftop.
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, 166 reviews

Executive Apartment on Lake Michigan with parking

DebraRating, 5 stars1 month ago
This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!
Guest favorite
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
4.84 out of 5 average rating, 152 reviews

The Spa of Downtown Whiting

SantiagoRating, 5 stars6 days ago
a really awesome place. I highly recommend this place.
Top guest favorite
The living room features warm pine walls, offering a cozy atmosphere. A dark, spacious sofa is positioned alongside a wooden coffee table. Two lamps illuminate the space, framed artwork adorns the walls, and potted plants are placed on the windowsill, adding a touch of greenery.
Guest suite in Andersonville
4.98 out of 5 average rating, 125 reviews

Cozy Andersonville Cabin

CydneyRating, 5 stars2 weeks ago
Loved staying here! Super cozy, easy to find, and Matt was always responsive and gracious letting me check in early and check out late. There’s a bathtub, a desk by a window perfect for working, and lots of great books. The hosts even left a complimentary bottle of wine and bag of chips! 10/10
Superhost
A contemporary living area is highlighted by a soft sofa and a round side table, topped with a small potted plant. A tall plant adds a touch of greenery, while a doorway leads to the bedroom area in the background, enhancing the spacious feel of the space.
Apartment in Whiting
4.84 out of 5 average rating, 163 reviews

NEW! |Studio Apartment Whiting IN, United States#2

JoeRating, 5 stars4 weeks ago
We were in town for a show at the Casino, this place was tremendous. Very easy to find, super close to the Casino and the room was quite nice. Would definitely book again if we find ourselves in that area again 😁

Dog friendly vacation rentals in Chicago

Guest favorite
A modern kitchen features sleek gray cabinetry and a spacious countertop. Stainless steel appliances, including a refrigerator and microwave, are visible. Natural light enters through a window above the sink, where a small flower arrangement is placed. The wood-inspired flooring complements the contemporary design.
Apartment in Joliet
4.95 out of 5 average rating, 203 reviews

*The Belltower Haven*Large*Family Friendly*Wi-Fi

RockyRating, 5 stars1 day ago
Great spot to stay and James was awesome, would highly recommend this place to any of my friends, thanks again!
Guest favorite
A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.
Guest suite in Portage Park
4.94 out of 5 average rating, 157 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

JulieRating, 5 stars1 week ago
Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!
Guest favorite
Townhouse in Old Town
4.85 out of 5 average rating, 169 reviews

Downtown Elegance ✨ Private Yard Parking

JohnRating, 5 stars3 days ago
Alex was great at communicating and following up. We had some questions and she was responsive. Also goes beyond expectations on things like forgetting coats :0) - thank you! The location is great. Short walk to a Main Street of bars and restaurants, kid friendly too - happy campers pizza joint was a great reco! Also close to the brown line train station and not too far into town - we walked it with children and it was fine. House is really large, spacious. I know some have mentioned about hearing the train, but that is part of city living, it was more than fine. Enjoyed the stay, would recommend it and would go back again if visiting Chicago. Thanks Alex!
Top guest favorite
A cozy living space features a light gray sofa adorned with decorative pillows, beside a small wooden table. A striking artwork is displayed above a shelf, while greenery is provided by potted plants near the window, enhancing the natural light in the room.
Apartment in Logan Square
4.98 out of 5 average rating, 130 reviews

Newly-renovated historic home in Logan Square

LynnRating, 5 stars2 weeks ago
I had a wonder stay at this charming flat in Chicago. Danny's home is a beautiful historical building full of character, and the interior was clean, comfortable and well maintained. One of my favorite parts was the cozy backyard-such a peaceful spot to relax on a warm morning or unwind in the evening. You're right in the center of activity, but have plenty of privacy. Danny was friendly, responsive and made everything super easy. I'd definitely stay here again and highly recommend it to anyone, and their dog, visiting Chicago!
Top guest favorite
A spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.
Condo in Logan Square
4.91 out of 5 average rating, 340 reviews

Susie's Space. 2BR easy parking & pet friendly

MegRating, 5 stars3 days ago
We loved our stay here. The place was very comfortable and spacious. The area was close to restaurants either walking distance or a short drive. Parking was super easy and Susan was very accommodating with us having 2 cars. Would highly recommend this place!
Superhost
A spacious backyard is surrounded by a wooden fence, featuring a well-maintained lawn. A large tree offers shade, while a set of red outdoor chairs is positioned around a small firepit. A children's playset is visible in a corner, enhancing the family-friendly atmosphere.
Home in Naperville
4.85 out of 5 average rating, 119 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Amanda RRating, 5 stars1 month ago
This home was absolutely beautiful and exactly what I wanted. I was looking for a large backyard to allow my dogs to run in while I stayed there. The yard is probably 3/4 of an acre and was excellent for the dogs. The driveway even extends beyond the privacy gate where you can pull your car right into it and let the dogs right out. It was perfect for loading the guys up early in the morning and letting them out late at night. I double checked the fence and she definitely reinforced a lot of it. There’s chicken wire on the bottom so the dogs can’t dig underneath it. The home itself is absolutely beautiful with a king size bed in the main bedroom, which has a window right to the backyard. It’s exactly what I needed for my 10 day stay Liz was also super responsive and super helpful for any questions that I had. I’m definitely gonna be able to stay here again.
Superhost
A cozy living area features a comfortable sofa against a sloped wall, complemented by two dark blue armchairs. Skylights above provide ample natural light, illuminating a patterned area rug beneath a wooden coffee table. Framed artwork hangs on the adjacent wall.
Apartment in Austin
4.82 out of 5 average rating, 179 reviews

Reno btrm; Big family escape, W/parking, love pets

LaurynaRating, 5 stars4 months ago
Very friendly and responsive hosts, thank you so much for accommodating us with our cat! Beautiful house and great location.
Guest favorite
A charming residential street is lined with historic brick buildings, showcasing architectural details such as rounded bay windows and decorative cornices. Lush trees provide shade along the sidewalk, with parked cars and softly glowing street lamps contributing to a serene atmosphere in the early evening light.
Townhouse in Lake View
4.84 out of 5 average rating, 114 reviews

Wrigleyville townhome two blocks from ballpark

GeoffRating, 5 stars3 weeks ago
The townhouse was amazing. We could have spent the whole time looking at the art and collectibles on the shelves and walls. The location couldn't have been more convenient to Wrigleyville and was a great neighborhood to walk the dogs around in.

Family friendly vacation rentals in Chicago

Guest favorite
The exterior of a charming Victorian house is showcased, featuring a white facade, large windows, and a decorative entryway. An American flag hangs from the porch, surrounded by greenery and a well-maintained pathway leading to the entrance.
Apartment in Lake View
4.9 out of 5 average rating, 183 reviews

Clean, spacious, walk to Wrigley! Self check-in!

JinnaRating, 5 stars1 week ago
We loved our stay. Amy was an excellent communicator. The space was clean, open and very inviting. I loved the location. I would definitely stay there again!
Superhost
A wooden deck features a large, rectangular table surrounded by matching chairs, accommodating several guests. A large blue umbrella provides shade, while the surrounding area showcases rooftops and greenery under a bright sky.
Apartment in North Center
4.85 out of 5 average rating, 266 reviews

Family Friendly 3BR Duplex in Roscoe Village

LanRating, 5 stars3 weeks ago
John was a very kind and responsive host. Answered any questions we had very quickly. Home was exactly as pictured and described. Very comfortable place to stay. Everything was clean. Appreciated the family and kid friendliness of the home--not a lot of decorative items in reach that could be broken, no tables with sharp edges, low bed in the upper guest room that was easy to get in and out. Location was close to several restaurants and grocery stores, and not too far a drive from all the major tourist attractions.
Guest favorite
A spacious living room features large windows draped with light curtains, allowing natural light to fill the space. A comfortable sofa and loveseat are positioned around a decorative area rug, with a television mounted on a cabinet. A rocking chair adds additional seating.
Apartment in Evanston
4.94 out of 5 average rating, 140 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

PreetiRating, 5 stars1 month ago
The place was clean and well kept .Letitia was very helpful and personable with local recommendations. I checked in late and there was a banana and apple waiting for me which really helped as it was too late for dinner but I was hungry. The kitchen is well equipped and the place is exactly as described. I had a wonderful stay.
Guest favorite
A bright, open living area features a gray sectional sofa, a coffee table, and a light-colored rug. Large windows provide ample natural light, while a ceiling fan adds comfort. A dining area and kitchen are visible in the background, enhancing the spacious feel.
Townhouse in Edgewater
4.95 out of 5 average rating, 259 reviews

The Nancy’s gorgeous , Spacious Urban Getaway

PeterRating, 5 stars2 weeks ago
Host is very accommodating and responsive. Felt just like home. We’ll be back!!
Guest favorite
A cozy living area features a spacious orange sectional sofa and a light blue armchair, complemented by a round coffee table with decorative items. A colorful area rug adds warmth, while wall art and woven baskets create visual interest. A TV and entertainment area are included.
Apartment in Oak Park
4.92 out of 5 average rating, 182 reviews

Large sunny 3BR apt. in downtown Oak Park

CraigRating, 5 stars1 month ago
This was a beautiful place! it had everything we needed. Oak Park downtown is walkable and has everything you could want. It is an upstairs unit so be prepared for some steps. Parking was easy. Michelle was great! Downtown Chicago is only 15m (if there's no traffic.). We would definitely come back!
Top guest favorite
A sunlit living area features large windows framed by wooden accents, allowing natural light to illuminate the space. A comfortable futon is positioned alongside an armchair and a glass coffee table on a textured rug, with a small television and simple wooden furniture completing the layout.
Apartment in Logan Square
4.95 out of 5 average rating, 509 reviews

2nd floor of 1908 brick two-flat in Logan Square

KathlynRating, 5 stars6 days ago
Thank you for sharing your wonderful space. It was perfect to spend time as a family while moving our daughter in Logan Square. The park nearby was so easy to manage for our dog who joined us. Paul was responsive and helpful. Got to meet his pup who was adorable. Will definitely stay here again
Guest favorite
The kitchen features modern appliances, including a stove and microwave, alongside a smooth countertop. A textured rug runs down the hallway, leading to a circular table situated in a well-lit space, characterized by warm brick accents on the walls.
Apartment in Lake View
4.93 out of 5 average rating, 204 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

HeatherRating, 5 stars1 week ago
The hosts were very responsive to any questions. They live in the same building and helped with any concerns right away. The space was very homey and comfortable, with convenient bus stops nearby. There were plenty of books, movies, and games if you have time to kill at the apartment. You can hear a lot of footsteps from upstairs neighbors, but usually it wasn't too loud and the provided earplugs were helpful. The neighborhood felt safe and family-friendly. It felt like we were staying with good friends. We highly recommend this place and would stay there again.
Guest favorite
The entrance to the vintage home is framed by lush greenery, showcasing a well-maintained front yard. A charming porch features seating near the steps, inviting relaxation. Large windows provide plenty of natural light, enhancing the home's welcoming appearance.
Apartment in East Rogers Park
4.84 out of 5 average rating, 211 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

ElijahRating, 5 stars1 month ago
Holly and Mark are great hosts. Very responsive and went above and beyond to offer additional help and recommendations for travel, food, etc during our stay.

Quick stats about vacation rentals in Chicago

  • Total rentals

    11K properties

  • Total number of reviews

    542K reviews

  • Family-friendly rentals

    5.2K 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

    6.9K 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, 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.


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.


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.

Frequently Asked Questions

  • How is the weather in Chicago?

    Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°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 2,010 house rentals, over 6,420 apartment rentals to over 1,060 condo 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago