Search Apartments in Winnetka

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Compare 1596 Apartments in Winnetka with updated reviews, rates, and availability.

1F Chicago's Little italy Graystone nearDowntown
Enjoy the Linden trees from the sunny bay window.

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (118)
"Great location walking distance of restaurants and some nightlife. Good neighborhood very safe college kids walking the streets not occasion. Are you really lazy lots of amenities more than usual in places like this and enjoyed our state would stay there again"
1F Chicago's Little italy Graystone nearDowntown
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Exterior detail

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

9.8 out of 10, Exceptional, (121)
"Had a really nice time. Great location."
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Living area

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

3.0 star property
8.2 out of 10, Very Good, (13)
"The property was excellent, for my stay "
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Open Concept Living Room

Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (211)
"Enough room for 2 kids and parents qith room to spare"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Living Room

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

10.0 out of 10, Exceptional, (264)
"This was a fantastic find. Loved the area - let’s hear it for yummy Italian food! The unit was well stocked with everything a guest might need. Highly recommend!"
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Cozy, Comfortable and Convenient apartment. Close to everything!
Living area

Cozy, Comfortable and Convenient apartment. Close to everything!

9.8 out of 10, Exceptional, (51)
"We really enjoyed our stay at this apartment. The apartment was nicely decorate, the couch was super comfortable and the bathroom was clean (the whole apartment was). It was just street parking which was fine. And it was in a great location as it was near the expressway. The only thing that makes this a 4 and not a 5 is the stairs to the apartment. They are extremely shallow and narrow. If you have any sort of mobility issues, I don't think I would recommend this listing. If that isn't a problem...
The price is SAR 451
SAR 1,024 total
includes taxes & fees
1 Dec - 2 Dec
Cozy, Comfortable and Convenient apartment. Close to everything!
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio

N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio

9.8 out of 10, Exceptional, (11)
"This is a clean and new-looking cozy mansard on the 2 story building. We liked the large kitchen, spacious bathroom, side-loading washer/dryer and a sizable bedroom. The biggest hurdle was finding parking after 10-11 pm. There might be more parking during day time. Freddy (host) nicely provided the daily parking passes, but we had to park on the adjacent street one of our 3 nights risking to get a parking ticket for the wrong location. On our last night there was a loud music/party in the...
The price is SAR 203
SAR 822 total
includes taxes & fees
1 Dec - 2 Dec
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio
Historic Oak Park Residence
Exterior

Historic Oak Park Residence

2.0 star property
9.4 out of 10, Exceptional, (6)
"This was quite a charming home. The access to public transportation was great. One mile walk or drive to parking garage. We ventured into the city every day but could have easily stayed in Oak Park."
The price is SAR 818
SAR 1,273 total
includes taxes & fees
26 Nov - 27 Nov
Historic Oak Park Residence
Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago
Interior

Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

9.2 out of 10, Wonderful, (17)
"Really nice place and the host was super helpful (he even answered when we called at almost 3 in the morning). It has almost every kitchen utensils except for a comal (us mexicans use it a lot lol) "
Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago
Charming Garden Apartment - Perfect for a Family Getaway by AllSet Turnover
Our bright living room is decorated with objects inspired by our love of Chicago - and traveling out of Chicago! Maybe you'll find some ideas here for your next vacation...

Charming Garden Apartment - Perfect for a Family Getaway by AllSet Turnover

8.6 out of 10, Excellent, (17)
"Basic unit with everything you need. "
Charming Garden Apartment - Perfect for a Family Getaway by AllSet Turnover
Large 3 bdrm / dining in the heart of Logan Square mins to DOWNTOWN
Interior

Large 3 bdrm / dining in the heart of Logan Square mins to DOWNTOWN

9.6 out of 10, Exceptional, (10)
"This is an older city home with updated bathroom and kitchen. The photos represent the property well. Plentiful street parking. We felt safe walking in the neighborhood. The owner was easy to contact and responsive. Would definitely come back!"
Large 3 bdrm / dining in the heart of Logan Square mins to DOWNTOWN
3BR Luxury Modern Apartment

3BR Luxury Modern Apartment

2.0 star property
10.0 out of 10, Exceptional, (3)
"Short sightseeing trip to Chicago."
3BR Luxury Modern Apartment
Adorable/Comfy/Free Parking/15min 2 DT Chicago/Apt
Living area

Adorable/Comfy/Free Parking/15min 2 DT Chicago/Apt

6.6 out of 10, (7)
"Excellent time in family in the apartment. 20 minutes to the Downtown of Chicago. We spent a great time in family. "
Adorable/Comfy/Free Parking/15min 2 DT Chicago/Apt
Chic & Historic Apartment Steps from Mag Mile
Living area

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (26)
"Very nice neighborhood, walking distance to Michigan Avenue, great food options, place has everything you need, I’ll stay there again, "
Chic & Historic Apartment Steps from Mag Mile
Chic, Cozy home, by Blue Line Train Stop + Free parking
Private kitchen

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.6 out of 10, Exceptional, (35)
"Very nice apartment. Could use more pillows (or fluffier). Just as advertised. "
Chic, Cozy home, by Blue Line Train Stop + Free parking
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!
Living area

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

9.0 out of 10, Wonderful, (70)
"Cozy duplex a short walk away to anything. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!
Oak Park Queen
Interior

Oak Park Queen

9.2 out of 10, Wonderful, (9)
"I was mostly confused about how to go about checking in so i had to call. We were told we would get an email soon telling us everything we needed to know which is fine, but we didnt know that till almost check in time. A minor inconvenience but not serious. Loved the area!"
The price is SAR 507
SAR 971 total
includes taxes & fees
26 Nov - 27 Nov
Oak Park Queen
The Roscoe Village Brownstone
Point of interest

The Roscoe Village Brownstone

9.8 out of 10, Exceptional, (11)
"Great location and we enjoyed our stay. Very clean code to food drink and train. Stairs were only challenge. We would come back"
The Roscoe Village Brownstone
Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!
Immaculate & bright extra-wide open entertainment lofted living room

Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!

10.0 out of 10, Exceptional, (81)
"Stayed for a reunion of friends after 20 yrs. Great location in Wrigleyville. Extremely well stocked kitchen. Plenty of comfortable beds and couches. Easy and quick communication from owners."
Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winnetka

Sentral Michigan Avenue
Garden

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is SAR 405
SAR 585 total
includes taxes & fees
26 Nov - 27 Nov
Sentral Michigan Avenue
Sonder Market Hall
Living area

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is SAR 240
SAR 281 total
includes taxes & fees
1 Dec - 2 Dec
Sonder Market Hall
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"This property was in a good location - walked to Shedd Aquarium, Soldier Field, and good restaurants on South Michigan. Asked a few questions via text with prompt responses. No complaints with this clean property exactly as advertised."
The price is SAR 465
SAR 546 total
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What's it like to stay at an apartment in Winnetka?
There are plenty of places to stay with in the Chicago area, with 4879 lodging choices including 2430 apartments. Top sights to discover during your visit include Lake Michigan.
How do you know if an apartment is the best choice for your stay?
An apartment is often more spacious than a traditional hotel room and comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples looking for something with a more local feel.
What's a favorite apartment for a stay in Winnetka?
Here’s a top apartment in the area: Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place: It’s located in Chicago, 16.7 mi/26.9 km from Winnetka. Includes free WiFi and Smart TVs.
What can I expect from the weather in Winnetka?
Though weather is just one factor, it can really affect your travel plans, especially if you’re planning an extended stay in Winnetka. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Winnetka is 48 inches.
What should I see in Winnetka?
Lake Michigan and Maple Street Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. Wrigley Field and Naval Base Great Lakes are other popular places to visit in the area.
What's the best way to get to and around Winnetka?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Chicago, IL (PWK-Chicago Executive), which is located 8.4 mi (13.5 km) from the city center. Otherwise, look for flights into Chicago O’Hare Intl. Airport (ORD), which is 12.5 mi (20.2 km) away. To explore the surrounding area, ride one of the trains from Winnetka Station or Winnetka Indian Hill Station.