
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
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Chic retreat near the best of Lakeview & Wrigley
Absolutely 5/5 everything looks exactly like the photos! The space is big, spotless, and feels incredibly cozy. The location is perfect…!!surrounded by everything you need, including Target, Whole Foods, Starbucks, Sephora, and a variety of restaurants and shops.

*The Belltower Haven*Large*Family Friendly*Wi-Fi
James is exactly the kind of airbnb owner you look for! House was extrmely clean and comfortable with lots of amenities! Highly recommend!

Bright two bedroom garden apartment
Were I in the Chicago area I wouldn’t hesitate to stay there again.

Comfortable Vintage North Side Retreat for 8
The space exceeded our expectations! It was quite large for an apartment with plenty of space for our large family of 6. We chose this place to be in proximity to Lincoln Square and be close to public transportation. I was initially concerned about being able to find parking, but even if we couldn’t find a spot right out front we still found something nearby. We absolutely loved how walkable the area is. We also enjoyed spending time reading in the front nook area by the windows and having a cup of coffee. Everything was great! The host checked in on us to make sure we were all good which I appreciated. Would definitely recommend this place and would 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.
Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.

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
Really lovely, cozy place near tons of cool neighborhood spots and transit. Felt right at home and really comfortable. Nikka was very proactive and kind. Would absolutely stay here again.

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!
We had a great stay in Kerilyn’s place. The unit is spacious, clean, and well-located near transit and a number of food options. Kerilyn was a great host as well. She responded quickly and was very helpful when we reached out to her for anything. It was very easy to check in and check out. I enjoyed my stay and would definitely stay again if visiting the Logan Square area again in the future!

CitySlickers Crash Pad /Free Parking /No Clean Fee
Kevin’s air bnb was great. Very clean and organized. We had available parking lot. Only the shower pressure was a little bit slower and could be better specially for washing the hair. All the rest was perfect.

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
Jenny went above and beyond! She was super communicative & very friendly. She even let me check in before checkin time, which I greatly appreciated. The apartment has literally everything you need. All the little details and small things you could want, are there. I would highly recommend staying here for a longer extent of time, as you would feel as if you’re in your own home.

Flexible Apt. for 8 by Oak Park-CHI
Lois is a great host! The accommodations were perfect for what we needed. Her space was clean and essentially everything you need from your airbnb. I will mention the beds are very uncomfortable:/ but that's the only thing I could complain about! thanks for having us :]

Family Friendly 3BR Duplex in Roscoe Village
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.

Vintage sunlit 2.5 BR apt. Perfect for families!
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.

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
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Skokie Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Odyssey Fun World
- Flossmoor Golf Club
- Moraine Hills State Park
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