
Apartment vacation rentals in Chicago
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Top-rated apartment rentals in Chicago
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals

Chic retreat near the best of Lakeview & Wrigley
Nice and clean 1 bed unit for a week of comfortable stay. Thank you for hosting us!!

*The Belltower Haven*Large*Family Friendly*Wi-Fi
Great spot to stay and James was awesome, would highly recommend this place to any of my friends, thanks again!

Bright two bedroom garden apartment
We had a wonderful stay at this charming city apartment. It was clean, well decorated, and stocked with all one could need. The location was ideal for exploring the city, with great restaurants, shops, and public transportation nearby. Parking our vehicle was never an issue with off street parking. The hosts were incredibly friendly, responsive, and accommodating - going out their way to make us feel at home. This was one of the smoothest and most enjoyable Airbnb experiences we have had. We would absolutely stay here again and highly recommend it to anyone visiting the area.

Comfortable Vintage North Side Retreat for 8
A great neighborhood spot! A cozy classic Chicago apartment with gorgeous midcentury accents. Extremely walkable and easy to access the Montrose brown line. The kids loved the trundle beds in the back sunroom. They have very smartly added blackout shades to the room to really create a child friendly sleeping space- a real gift! Loved the whole place, would love to stay there again!

Vibrant Lg Chicago 2BR Close 2 Everything & Nature
Tiffany’s place is so comfortable and charming. Beautifully decorated, with comfortable furniture/beds and a fantastically appointed kitchen, you won’t regret booking this spotlessly clean gem. As a coffee snob, the electric kettle and French press were a dream come true. The plants everywhere make it feel warm and inviting and the turntable was a delightful surprise that we really enjoyed. We could not have been more pleased with this beautiful and cosy home.

*Comfortable & Spacious Home Close to Downtown*
This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.

Oasis Collection's Mid-Century 3 Bd Wicker Park.
This is a very clean and comfortable unit. The beds are very comfy, the comforts are wonderfully soft. Basic toiletries and kitchen essentials are provided. The location is excellent for us, as we have young grandchildren and a dog, both enjoyed wicker park. Many restaurants are close enough for walking.

BERNARD CHATEAU - LOGAN SQUARE
it was my first Airbnb experience and it was very pleasant. The location is perfect to get to the place, but perfectly peaceful in the night.
Apartment rentals with air conditioning

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Happy I found this listing and stayed. great Host, cummicated and was exactly as advertised. good location a few blocks from downtown 10-15 minutes walking. would definitely stay again.

Lovely 2bedroom 1bath Apt and outdoor seating.
A very nice and welcoming place to stay!

New apartment
Loved the walkability and great access to transit and chinatown restaurants. amazing stay! thank you!

Cozy 1BR in the heart of Logan Square
Nikka’s place was clean, cozy, well decorated. Easy to find parking on that street. Bed was very comfortable and lots of extra linens if you get chilly. It was a very quiet building. Really enjoyed walking in the neighborhood and being so close to great restaurants and fun things to do.

Huge Pet Friendly East Albany Park Apartment
Hugh's place was nice! It's in a cute, quiet neighborhood with most things you need within a ten minute walk. The spot itself was big with lots of plants and nice touches, and both check in and communication were great. We needed an early check in coming from another Airbnb and it was no problem. Overall, it's a good spot to explore the northern side of Chicago from. I'd stay again!

Pelotoning while Airbnb'ing in Chicago!
Can't say enough good things about this place! This was our first visit back to Chicago after moving away last year, and we already can't wait to go back (and stay here). I cannot stress this enough -- you CANNOT beat this location. I'm a Logan Square evangelist for life, and this is one of those perfect little side streets that's quiet, tree-lined, with plenty of parking, but also steps away from plenty of things to eat, drink, and do. Other things I loved: the apartment was very clean, the beds were super comfy, and there were lots of board and table games available for us to play. We were there as a family of four and it was just the right amount of space. One of the bedrooms is big enough to comfortably fit a travel crib on the floor (which we did). The kitchen is well appointed and we were able to make most of our meals there. Kerilyn and co were extremely responsive and friendly hosts. We can't wait for our next visit!!

CitySlickers Crash Pad /Free Parking /No Clean Fee
Just what I needed to get away. Perfect place. It was so peaceful and the bed was extremely comfortable. Loved everything about it. I Will definitely be back.

Great Location Studio
This was a great spot. Clean and in a central location to downtown with easy access to transit. Would stay gain next time I’m in town.
Family-friendly apartment rentals

Cozy Garden-Subterranean Apartment
This is the perfect place for a cozy Chicago getaway, very clean, peaceful, great location, and probably the most well-stocked Airbnb I’ve ever stayed in. Jenny is very friendly and responsive. I would stay here again in a heartbeat!

Flexible Apt. for 8 by Oak Park-CHI
We had a wonderful stay! Lois was very responsive and made everything easy from start to finish. The house was cozy, clean, and well-equipped with everything we needed. Parking was super convenient, and the neighborhood felt safe and quiet. It was a perfect spot to relax after a day out. Highly recommend!

Family Friendly 3BR Duplex in Roscoe Village
It was really good. It's an older building so it had old-building problems (creeky floors kinda thing). Other than that it was perfect for our family of four: enough room to do our own thing, enough room to be together.

Vintage sunlit 2.5 BR apt. Perfect for families!
I enjoyed my stay at Letitia's place. I was traveling between the city and northern burbs, and Letitia's place provided a nice centralized location with easy access to both. Letitia's place is clean, charming, and comfortable. Letitia responded quickly to any questions. I recommend this as a comfortable place to explore the greater Chicagoland area.

Garden Apartment in captivating Hyde Park
Nice location with nearby supermarket, cafes and restaurants. The nearby busstop to go downtown is also very nice and near. Great apartment with all the necessary amenities for short stay. 😁

Adorable 1BR apartment near Northwestern
Nice place to stay in a good neighborhood! Would stay here again, thank you!

Bright, Cheery Logan Square Getaway
Great location! The place was very easy to find and within walking distance some really good restaurants. Loved our stay!

2nd floor of 1908 brick two-flat in Logan Square
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
Quick stats about apartment rentals in Chicago
Total rentals
6.4K properties
Total number of reviews
306K reviews
Family-friendly rentals
3.1K properties are a good fit for families
Pet-friendly rentals
2.2K properties allow pets
Rentals with a pool
840 properties have a pool
Rentals with dedicated workspaces
3.9K properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Lincoln Park
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Flossmoor Golf Club
- Brookfield Zoo
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
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