Chicago apartment rentals
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Top-rated places to stay in Chicago
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
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Popular amenities for Chicago places to stay
Chicago house rentals
Home in West Lawn
4.92 out of 5 average rating, 24 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
The home was clean & exactly as shown in pics! Would recommend to a friend. Stayed with 5 people and still had plenty of space. Location was quiet! I lovvved the spiral staircase in the home.
Home in Lincoln Park
4.94 out of 5 average rating, 122 reviewsWrigley Retreat - Full Home w/ Chicago Charm
Dustin was a great host! Super quick response to a few questions we had while we were there. The space was outstanding! Plenty of room for all 7 of us and everything was there that we needed-and then some!! We thoroughly enjoyed our stay.
Home in Roscoe Village
4.94 out of 5 average rating, 252 reviewsDuplex Home RoscoeVillage/Wrigley Free St Parking
Sharleen was a great host and very responsive. She mentioned there being a lingering smell from the previous tenants, which my party and I definitely noticed upon arrival, but left the windows open while we were there to air it out. The location is great and very walkable to locals shops and cafes/restaurants .
Home in Blue Island
4.81 out of 5 average rating, 182 reviewsWarm and comfortable inviting Suburban home !
Rich's place was the perfect location for us. We needed to get to the city for the Chicago Marathon, but didn't want to stay IN the city. Check in and check out were easy. The place was clean, spacious, and comfortable. Thank you!!
Home in Bolingbrook
4.92 out of 5 average rating, 116 reviewsThe Sunshine Spot
House was perfect all around. Location was amazing being so close to stores and major highways!
Home in Homer Glen
5 out of 5 average rating, 3 reviews4 bedroom home rental in quiet neighborhood
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Home in Itasca
5 out of 5 average rating, 46 reviewsRANCH, House-tel: updated full kitchen, comfy beds
What a great place! Quiet street with lots of large beautiful trees, great for a walk with the stroller. House back up on a community park with playground and tennis court, close to everything. Will absolutely stay again.
Home in Homewood
4.91 out of 5 average rating, 118 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
this place was great!! we will be back!!
Chicago places to stay
Rental unit in Oak Park
4.87 out of 5 average rating, 270 reviewsCosmopolitan Nest in Oak Park North Side
A great place for 1-2 people looking for a place to stay while exploring Oak Park. Bed was comfortable, bathroom had plenty of space, and the mini fridge + microwave was greatly appreciated. Would definitely recommend!
Rental unit in Chicago Ridge
4.83 out of 5 average rating, 6 reviewsSmart Crib Stay
we had a fantastic stay at this property, the house was exactly as described, very clean, comfortable, and well maintaned. the host was estremely welcoming and responsive. the location was perfect
Home in Maywood
4.81 out of 5 average rating, 98 reviewsMaywood Relaxation
My friends and I had an amazing weekend in Chicago. this home had everything it says in the description. Robert was very helpful and made are staying very comfortable and relaxing would be staying here in the future:)
Home in Joliet
4.92 out of 5 average rating, 171 reviewsThe Garden House - Murals and more
No problem checking in, even late at night. Clean and cozy
Rental unit in Wicker Park
4.88 out of 5 average rating, 34 reviewsPierce Place in Wicker
My husband and I stayed at Jacqueline's house for a weekend and would definitely come back. The house is on a beautiful and quiet side street that is in walking distance to the blue line, great restaurants, shopping, coffee shops, etc. The house itself is perfectly homey, very clean, well stocked, and has a really comfortable bed. I especially appreciated that there were coffee beans/creamer in the cupboard and fun coffee mugs to choose from. I highly recommend staying here for the house itself as well as the great neighborhood. It made me feel like a local staying here.
Home in Wood Dale
4.91 out of 5 average rating, 32 reviewsCozy 2 bedroom home in a wonderful neighborhood.
Joanna’s Airbnb was in a quiet, safe location. It was clean and tidy and quite a cute place to stay. Super comfortable and close to Ohare!
Townhouse in Bronzeville
4.79 out of 5 average rating, 14 reviewsBronzeville 10minsdowntown SelfCheckin WasherDryer
Very nice and comfortable stay! Close to downtown Chicago so easy transportation. The inside is very cozy and overall, no complaints!
Rental unit in Berwyn
4.87 out of 5 average rating, 23 reviewsLa Casita Near Midway&Downtown
This is my 2nd airbnb I have rented from Teresa and she is such a pleasure to communicate with and is a great host
Chicago fishing apartment rentals
Rental unit in East Rogers Park
4.88 out of 5 average rating, 114 reviewsRock Star Beach Pad on Lake Michigan with parking
Fabulous place to stay with parking included. Comfortable beds, great showers all with peaceful views of Lake Michigan. 4 nights flew by. Easy walking around the local area and access to train into downtown. A memorable and enjoyable end to our trip from Australia. If we are ever lucky enough to be back in Chicago this is where we will stay.
Rental unit in Lincoln Park
4.71 out of 5 average rating, 108 reviewsThe Biddle House (#1)
The property was exactly as described! The location in excellent! It's a beautiful neighborhood and a quiet street. This is my second time staying on the property and I'll definitely be back again! Thanks Elizabeth
Rental unit in Evanston
4.97 out of 5 average rating, 452 reviewsCharming, Sunny Apartment with Backyard Garden
This is a beautiful old home that has been lovingly maintained. It is extremely clean and it’s comfortable and cozy both inside and out. Susan is very friendly and responsive. I felt well taken care of. I hope to be back. Highly recommended!
Rental unit in Evanston
4.82 out of 5 average rating, 164 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
We have been multiple stay guests, and wouldn't consider staying anywhere else but here, when whenever traveling to the area! We are already booked in both units this coming week as well! 😊
Rental unit in Andersonville
4.93 out of 5 average rating, 418 reviewsAndersonville Living
Joseph’s place is in a quiet neighborhood but so so close to a bunch of awesome shops and restaurants! You’ll feel at home but in a city. Joseph is also super nice.
Rental unit in Skokie
4.97 out of 5 average rating, 131 reviewsCharming Apt.Fully Equipped Prk.Inc 12 min 2 Lake
Loved the place. Was very well stocked with all the essentials. Very conveniently located. Lots of cute restaurants nearby.
Rental unit in Near North Side
4.93 out of 5 average rating, 138 reviews*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
GREAT HOST AND GREAT LOCATION.
Rental unit in Whiting
4.85 out of 5 average rating, 140 reviewsNEW! |Studio Apartment Whiting IN, United States#2
A nice place to stay for a night or two. It was a quick drive to Chicago for us. Marlen was a very responsive host and communicated well throughout our entire stay.
Quick stats about vacation rentals in Chicago
Total rentals
11K properties
Total number of reviews
514K reviews
Family-friendly rentals
5K properties are a good fit for families
Pet-friendly rentals
3.4K properties allow pets
Rentals with a pool
1.1K 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 6,100 apartment rentals, over 1,080 condo rentals to over 1,900 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 6,910 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.
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