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Check prices for these dates

Next weekend
Mar 21 - Mar 23
In two weeks
Mar 28 - Mar 30
In one month
Apr 11 - Apr 13
In two months
May 9 - May 11

Browse Select Winnetka Apartments

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!
3 bedrooms, WiFi, bed sheets

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

9.2 out of 10, Wonderful, (73)
"Loved this location near Wrigley Stadium. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Point of interest

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (225)
"Best vrbo host ive ever had"
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

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

9.4 out of 10, Exceptional, (44)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (16)
"Really nice location and a good place to stay. There's not a full kitchen but there is a kitchenette. We were out and about most of the time so that was no problem for us. Great neighborhood. "
Charming Wrigleyville Home Close to the Cubs!
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Aerial view

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

10.0 out of 10, Exceptional, (278)
"The apartment was very cute and clean, had all the necessities we needed and then more! We really appreciated the set up. The neighborhood is great and safe as well! "
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Beach

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

9.8 out of 10, Exceptional, (132)
"Couldn’t have asked for a better experience. I was looking for a place to stay while visiting my daughter who lives in the dorms at DePaul, after figuring out there really aren’t hotels close by. The space was clean, well maintained and nicely updated, check in was seamless and communication was great, plenty of space for my daughter and I to hang out and enjoy some carryout together. The location was ideal, a few minutes to walk to multiple coffee options, 15 minutes to my daughters dorm so we...
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (32)
"I didn’t realize when I booked this unit that I would have to carry my luggage up two flight of stairs. Unit is spacious, bathroom is a little tight the only issue I experienced was NOISE, first two nights it was the heater (I think) the last night I could hear foot steps from above and on the early morning of Monday it sounded like construction. Location is great if you want to be steps from high end shopping and restaurants. "
Chic & Historic Apartment Steps from Mag Mile
One half block from Lincoln Park and the zoo
Exterior detail

One half block from Lincoln Park and the zoo

9.8 out of 10, Exceptional, (106)
"Clean and a perfect location for you in Chicago! Book it. This is my second time and everything was perfect."
One half block from Lincoln Park and the zoo
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Smart TV, DVD player, books, stereo

Stylish, Inviting 2-BR near Logan Square and Wrigley Field

10.0 out of 10, Exceptional, (44)
"Loved the art, books, games, comfy mattresses, clean linens… this place has it all!"
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Experience Chicago in Hip Logan Square
Exterior

Experience Chicago in Hip Logan Square

9.2 out of 10, Wonderful, (5)
"Very clean townhome with all the necessary amenities. Owner was quickly responsive to all communications. Relatively quiet neighborhood. Next door neighbor had a Halloween party on a Sunday night that lasted until 3am. Wasn’t horribly loud but could hear enough noise that I needed to use my noise canceling headphones to sleep. The other nights were very quiet and peaceful. Would stay there again in the future. "
Experience Chicago in Hip Logan Square
Remodeled West Loop Apartment Near United Center
Interior

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (34)
"Everything was nice and neat. They were super easy to communicate with. We had a little issue with the main building door keyless entry. Other than that everything was great."
Remodeled West Loop Apartment Near United Center
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.8 out of 10, Exceptional, (6)
"My wife and I were attending a show and stayed for a night. It's fairly close to the Aragon Ballroom and has lots of dining options nearby. The host was attentive and easy to reach. He even shoveled the snow at 11pm; as it had snowed during the show and when it was over several inches had fallen. Well done sir, cleanest walk in the neighborhood.Everything in the apartment was clean and comfortable."
The price is CA $142
CA $380 total
includes taxes & fees
Mar 11 - Mar 12
2-bedroom apartment just 2 minutes drive to Wrigley Field
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Pool

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (93)
"Great place for me to stay for work travel! Bed is cozy and Jamie does a fantastic job making guests feel welcome and comfortable. Location was super cute as well. I would definitely stay here again. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Beach

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

10.0 out of 10, Exceptional, (214)
"Beautiful property.. very responsive host .. above and beyond what we expected.. and Peefect location for us .. near our daughter’s new Roger’s park apartment !! Highly recommen "
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Entire Below Level Studio w/ Private Sauna
Property grounds

Entire Below Level Studio w/ Private Sauna

10.0 out of 10, Exceptional, (34)
"A good small apartment in a great area of town. Would have loved to have the heater thermostat control downstairs, to control the temperature as we came int the apartment. As it turns out, the weekend we stayed was frigid cold and we needed the apartment to be warmer throughout. Everything else was perfect."
Entire Below Level Studio w/ Private Sauna
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Point of interest

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

9.6 out of 10, Exceptional, (78)
"Ali is a terrific host! He responds immediately whenever there is an issue or question.The apartment is perfect. Walking distance to shopping, restaurants, parks. Very secure and love the off street parking.I have visited this property 6 times snd it is always great!"
The price is CA $183
CA $356 total
includes taxes & fees
Mar 12 - Mar 13
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Fridge, microwave, oven, stovetop

Perfect 4 Bedroom/3 Bath in the HEART of Old Town

10.0 out of 10, Exceptional, (55)
"Quiet, fun place to stay. The apartment was clean, and exactly what we were looking for. Didn't see a single neighbor during our stay. There are a lot of stairs, just in case you overpack and have a gigantic suitcase. The beds were comfortable. One of the queen bedrooms does not have exterior windows, there's a window above the door, but that just made it the quietest room in the place. Very cute, we'll be back!"
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Oak Park Queen
Exterior

Oak Park Queen

9.4 out of 10, Exceptional, (12)
"Wonderful place. Stayed four nights and went in and out to visit family in Oak Park and nearby neighborhoods. Everything you will need when looking for a place to stay. Clean, roomy, comfy and had everything we needed!Consider staying here!"
The price is CA $194
CA $369 total
includes taxes & fees
Mar 11 - Mar 12
Oak Park Queen
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Fridge, microwave, oven, stovetop

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

10.0 out of 10, Exceptional, (104)
"It was exactly as expected. Clean and easy check in and check out well supplied!"
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
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
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (695)
"Amazing and clean experience I highly recommend "
The price is CA $182
CA $256 total
includes taxes & fees
Mar 11 - Mar 12
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (447)
"A great stay! I’d definitely come back."
The price is CA $136
CA $160 total
includes taxes & fees
Apr 1 - Apr 2
Sonder South Wabash
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (145)
"⭐️⭐️⭐️⭐️⭐️ Had a fantastic stay at Sonder Chicago West Loop during my business trip! The location was perfect for meetings, and I loved having the extra space. The studio felt more like an apartment—super clean, spacious, and well-appointed with stylish decor. The kitchen was fully stocked and well-maintained, making the stay even more comfortable. The reception area was great for getting work done before check-in, and the luggage room lockers were a huge plus. The app-based entry system was...
The price is CA $180
CA $212 total
includes taxes & fees
Mar 11 - Mar 12
Sonder The Burnham Apartments
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 5080 lodging choices including 2577 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?
Listed below are some of the top apartments in the area: Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!: Situated in Chicago, 12 mi/19.4 km from the heart of Winnetka. Includes Smart TVs. Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago: It’s situated in Chicago, 16.1 mi/26 km away. Includes free WiFi, separate dining areas, and Smart TVs. Experience Chicago in Hip Logan Square: 13.3 mi/21.4 km away in Chicago. 3F Vintage Graystone in Little Italy near 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.