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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
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Living area
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
9.4 out of 10, Exceptional, (10)
"Place is what was advertised. It was everything i needed. It was 5 mins from family. Parking in yard was great! Host called to check on us!! He was very responsive before arriving and after!! Would stay again. "
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Charming Chicago Retreat with Modern Comforts - Spa Bath
Outdoor dining
Charming Chicago Retreat with Modern Comforts - Spa Bath
9.8 out of 10, Exceptional, (19)
"Stayed 3 nights to explore the Logan Square area. Listing was just like the pictures and there was plenty of space for 2. Property manager was very quick to respond to questions and we had no trouble accessing the parking. Would absolutely stay again. "
Charming Chicago Retreat with Modern Comforts - Spa Bath
New Garden Studio near Wrigley/DePaul/Dwtn
New Garden Studio near Wrigley/DePaul/Dwtn
9.6 out of 10, Exceptional, (7)
"All good"
New Garden Studio near Wrigley/DePaul/Dwtn
Beautiful apartment in peaceful Elk Grove
Lobby
Beautiful apartment in peaceful Elk Grove
Beautiful apartment in peaceful Elk Grove
Cozy modern unit w/ easy access to downtown Chi
Living area
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (33)
"Clean, exactly as described and reasonably priced. Also a great location to access public transit & lots of restaurants nearby. Had a great stay!"
Cozy modern unit w/ easy access to downtown Chi
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Private kitchen
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (163)
"The location is close to the bus, and then easy to the Metro. It was about a 40ish min travel to the Art Institute when we were there. Roscoe Village is picturesque. There is a Starbucks at the end of the street if you want your pumpkin spice latte, but they've also got plenty of local talent- the owner of Rudy's Bakery (try the butter cookies YUM!!)-was lovely. There were plenty of other places--we just didn't have time! We arrived on Halloween; the entire neighborhood came out on their front...
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Chic & Historic Apartment Steps from Mag Mile
Living area
Chic & Historic Apartment Steps from Mag Mile
9.8 out of 10, Exceptional, (25)
"This property was perfect for our weekend in Chicago. The surrounding area was cute and had lots of restaurant options. We were in town for the marathon so I appreciated being close by to a grocery store and the red line. The stop to the red line was a short walk and made getting to the start line a breeze."
Chic & Historic Apartment Steps from Mag Mile
Beautiful Unit CHI in Prime River North - 3
Living Room / Dining Room with Fully stocked kitchen
Beautiful Unit CHI in Prime River North - 3
10.0 out of 10, Exceptional, (12)
"I had an amazing stay! The place was exactly as described—spotlessly clean, beautifully decorated, and super comfortable. The host was incredibly welcoming and provided excellent local recommendations. The location was perfect, with easy access to restaurants and attractions. I couldn’t have asked for a better experience. I’ll definitely be back!"
Beautiful Unit CHI in Prime River North - 3
Wrigley/Southport Corridor Garden Oasis +parking!
Living area
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (65)
"Property was very clean and well maintained. Great location! "
Wrigley/Southport Corridor Garden Oasis +parking!
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, (34)
"The house & the apartment were very clean & cute. Neighborhood was nice & felt safe. My only complaints were that we would’ve liked more than 2 bath towels for two people for 3 days. Also, it was very warm in the apartment (no air conditioning), but who could’ve known it would be 80 degrees in mid-October. Thank goodness there was one fan provided."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
Bright, open-concept living space and kitchen
Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
8.0 out of 10, Very Good, (10)
"10 min walk from nearest train station"
Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
Walk to Wrigley Field/Monthly Discounts Available
Panoramic view of Living room with 50 inch flatscreen TV!
Walk to Wrigley Field/Monthly Discounts Available
9.6 out of 10, Exceptional, (122)
"Location was perfect, mostly clean, just needed wash cloths, some papertowels & at least an extra roll of TP. Louder group up top but expected that being in an apartment. Overall we would stay again. "
Walk to Wrigley Field/Monthly Discounts Available
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
20 Nov - 21 Nov
Oak Park Queen
Sunny Coach House in Historic Oak Park
Living area
Sunny Coach House in Historic Oak Park
9.8 out of 10, Exceptional, (47)
"Hosts were great place check on easy! Would stay again."
Sunny Coach House in Historic Oak Park
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover
Flooring,Chair,Furniture,Living Room,Room
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover
8.4 out of 10, Very Good, (16)
"The apartment suited our needs. We were in town to take care of some family business. Apartment was spacious and the location was perfect for us. Plenty of shopping and restaurants nearby."
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Living room offers comfortable chair, loveseat and a sofa that turns into a bed.
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
9.6 out of 10, Exceptional, (70)
"Booked this place for my family who visited for my wedding. Everything was clean and just as described. The location was super easy to find and instructions were clear. Good location close to Downtown Oak Park and close enough to talk to the train station if needed. Ali was very nice and available via message. Thank you so much!!"
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Breathtaking Downtown Penthouse B - Sleeps 11
Breathtaking Downtown Penthouse B - Sleeps 11
8.8 out of 10, Excellent, (18)
"Roof deck was great. Awesome location. Would stay there again"
Breathtaking Downtown Penthouse B - Sleeps 11
Experience the Best Sites in Chicago & Rest Easy at the End of the Day by AllSet Turnover
Plenty of room to relax in my top floor Wrigleyville apartment!
Experience the Best Sites in Chicago & Rest Easy at the End of the Day by AllSet Turnover
10.0 out of 10, Exceptional, (7)
"Great place. Clean, well stocked with coffee, tea, ample paper products (tp, tissues, paper towels). Also shower products. Quiet neighborhood and close to the places we wanted to be. Rooms were as described. "
Experience the Best Sites in Chicago & Rest Easy at the End of the Day by AllSet Turnover
Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO
Lovely living room with sofa sleeper.
Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO
8.4 out of 10, Very Good, (10)
"It was a good place to stay for fanexpo "
Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO
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, (586)
"It was beautiful,clean and quiet "
The price is SAR 485
SAR 679 total
includes taxes & fees
8 Dec - 9 Dec
Sentral Michigan Avenue
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (203)
"Overall, we really enjoyed our stay! The area was lovely and quiet, so nice to sit at the park right beside! I was worried about the noise when it came to sleeping, but I was able to sleep soundly (i did have noise cancelling headphones on though). The bed was super comyfy! The walls are thin though, we could hear conversations and music. This place was very accommodating! They have everything as stated in their listing. The kitchenette is so great! Staff was very friendly whenever I had...
The price is SAR 258
SAR 303 total
includes taxes & fees
10 Dec - 11 Dec
Sonder Market Hall
Sonder South Wabash
Living area
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (389)
"Clean and well located. We had access to the green and red line trains a few stops away from the loop. Entering the building was easy and convenient. Apartment was clean and spacious!! "
The price is SAR 480
SAR 563 total
includes taxes & fees
11 Dec - 12 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 4859 lodging choices including 2426 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 popular apartment in the area: Wrigley/Southport Corridor Garden Oasis +parking!: 12 mi/19.3 km away in Chicago. Amenities include 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.