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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Winnetka apartments

TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is CA $184
CA $358 total
includes taxes & fees
May 26 - May 27
Sunlit 1BR Apartment | Warm & Welcoming Space
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is CA $364
CA $828 total
includes taxes & fees
May 26 - May 27
River North Rooftop With In and Out Parking 3
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is CA $184
CA $358 total
includes taxes & fees
May 26 - May 27
West Loop Living – Bright 1BR
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is CA $155
CA $307 total
includes taxes & fees
May 25 - May 26
Chic Studio in the Heart of the Gold Coast
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is CA $183
CA $356 total
includes taxes & fees
May 26 - May 27
Chicago-Themed 1BR in a Central Spot near Downtown
Property grounds

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (74 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is CA $197
CA $470 total
includes taxes & fees
May 21 - May 22
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is CA $521
CA $1,058 total
includes taxes & fees
May 24 - May 25
River North Rooftop With In and Out Parking 6
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is CA $497
CA $1,187 total
includes taxes & fees
Jun 17 - Jun 18
Modern West Loop Gem-City Views & Prime Location 6
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is CA $175
CA $239 total
includes taxes & fees
May 21 - May 22
LIVN Millennium Park Downtown Chicago Studio
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is CA $225
CA $305 total
includes taxes & fees
May 25 - May 26
LIVN West Loop Chicago 2 BR City View
Fridge, microwave, oven, stovetop

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is CA $126
CA $310 total
includes taxes & fees
Jun 16 - Jun 17
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is CA $191
CA $367 total
includes taxes & fees
May 26 - May 27
1BR Modern Luxe Apt with In-Unit Laundry
Dining

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Berwyn
9.0 out of 10, Wonderful, (17 reviews)
"It's a great place to stay, honestly, the hosts are nice and there to help you as well.The place is big, it has good A/C, and lots of space for different activities.Finally, there's lots of parking available in case you are using a car."
United States
Juan Pablo T.
The price is CA $74
CA $212 total
includes taxes & fees
May 21 - May 22
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Interior

Stunning & Stylish Downtown Studio - Highland Park

Stunning & Stylish Downtown Studio - Highland Park
Highland Park
8.4 out of 10, Very good, (7 reviews)
"Great location, quiet area, easy walking into town for breakfast etc"
United States
Tom B.
The price is CA $163
CA $304 total
includes taxes & fees
May 21 - May 22
Stunning & Stylish Downtown Studio - Highland Park
Terrace/patio

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (48 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is CA $142
CA $333 total
includes taxes & fees
May 26 - May 27
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Interior

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

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (100 reviews)
"Everything was good!"
United States
Brio
The price is CA $172
CA $387 total
includes taxes & fees
Jun 2 - Jun 3
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Smart TV

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is CA $132
CA $237 total
includes taxes & fees
May 21 - May 22
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is CA $582
CA $1,168 total
includes taxes & fees
May 24 - May 25
Spacious 4BR Central Apartment w/ Skyline Views
Fridge, microwave, oven, stovetop

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
8.0 out of 10, Very good, (10 reviews)
"Cozy, private, clean. A quick walk to the train and busses. Would stay again."
United States
John D.
The price is CA $227
CA $551 total
includes taxes & fees
May 21 - May 22
Cozy apartment with AC and WiFi in awesome Chicago
TV, offices

1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
7.8 out of 10, Good, (9 reviews)
"Great location, very clean. Easy check in and check out. Great communication."
United States
Thomas L.
The price is CA $122
CA $275 total
includes taxes & fees
May 26 - May 27
1BR/1BA City Comfort
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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Top Winnetka Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"It was very clean and met standards "
Natalia 2-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Winnetka

Winnetka Apartments information

Number of reviews
346
Accommodation
1324 Apartments
Lowest Price
CA $212
Highest Price
CA $1,187

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 5552 lodging choices including 1684 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 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.

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