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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 200 Condo Rentals in Winnetka with updated reviews, rates, and availability.

Stunning 3 BR in prime Chicago location
Living area

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (88)
"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."
Stunning 3 BR in prime Chicago location
Wrigleyville Inn - Unit 3
1

Wrigleyville Inn - Unit 3

10.0 out of 10, Exceptional, (24)
"We took the MLK weekend to get away to Chicago to do some brewery hopping and exploring neighborhoods away from the usual downtown attractions. This was the perfect location for walking around and getting to Wrigley Field. The unit is fresh, clean and very comfortable. "
Wrigleyville Inn - Unit 3
Wrigleyville Inn - Garden Unit
1

Wrigleyville Inn - Garden Unit

10.0 out of 10, Exceptional, (22)
"The garden apartment was perfect for our family gathering. The location is convenient and in a nice neighborhood. The layout provided all of us privacy when we needed it and plenty of room for celebrating! "
Wrigleyville Inn - Garden Unit
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Furniture,Indoors,Living Room,Home Decor,Couch

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

10.0 out of 10, Exceptional, (22)
"We were visiting our nephew, who lives around the block from this rental, so we didn't spend a lot of time in the rental, but it was absolutely sparkling clean, well-appointed, and lovely. We will definitely book it again. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
NEW LUXURY CONDO WITH PATIO DECK
Room

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (155)
"We love this well stocked condo. The location, off street parking and amenities make it a great home away from home for us. "
NEW LUXURY CONDO WITH PATIO DECK
Classic Lincoln Park 2 bedroom condo- parking included
Exterior

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (63)
"The condo was well equipped including dishwasher and washing machine. Location was convenient to Fullerton bus and Metra line to Evanston. We enjoyed our stay!"
Classic Lincoln Park 2 bedroom condo- parking included
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena
Living Room with 2 sofa beds

3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena

9.6 out of 10, Exceptional, (22)
"Pics didn’t really line up with the place, but that’s okay. Area was pretty safe, easy to drive around. Hard to get ahold of owners at times, but besides that, it was a good time."
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena
Walking distance to restaurants, shops and Lake Michigan,
Stunning open floor plan is perfect for entertaining and gatherings.

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (196)
"Great property and easy process to check in/out. Lots of space and privacy. It was easy to get around and explore the city. "
Walking distance to restaurants, shops and Lake Michigan,
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Home Decor,Furniture,Indoors,Living Room,Table

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.6 out of 10, Exceptional, (24)
"The place was super nice, very clean, and quiet. It was perfectly located for our needs. We were visiting my daughter and brand new granddaughter, and hope to make it our new home away from home when we visit."
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Gorgeous 3BR River North Condo - Free Parking
Living area

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (9)
"Great location. Central to everything. I will stay here again the next time I visit Chicago. "
Gorgeous 3BR River North Condo - Free Parking
Spacious, Clean and Steps from Wrigley Field!
Dining Room

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (7)
"Great host, very responsive "
Spacious, Clean and Steps from Wrigley Field!
The Inn at Wrigleyville, Beautiful New 4 Bedroom Sleeps 9
Room

The Inn at Wrigleyville, Beautiful New 4 Bedroom Sleeps 9

9.8 out of 10, Exceptional, (20)
"We had a wonderful time meeting friends for the weekend. The proximity to the stadium is the best. "
The price is AED 1,759
AED 3,936 total
includes taxes & fees
28 Feb - 1 Mar
The Inn at Wrigleyville, Beautiful New 4 Bedroom Sleeps 9
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Living area

"Melody of Evanston" 3BD, 2BA UrbanLux Condo

2.0 star property
10.0 out of 10, Exceptional, (7)
"The property was wonderful! It was clean and located perfectly for getting around the north shore. We enjoyed our visit!! "
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Chic 2-bedroom Condo near McCormick Pl with Parking Spot
Living area

Chic 2-bedroom Condo near McCormick Pl with Parking Spot

Chic 2-bedroom Condo near McCormick Pl with Parking Spot
Experience Chicago living near United Center
Interior

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (13)
"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."
Experience Chicago living near United Center
Downtown Park VIEWS Mich Ave, Museums 2bd/2ba
Welcome to our newly renovated 2bd/2ba apt on Mich Ave w/ Lake Michigan views!

Downtown Park VIEWS Mich Ave, Museums 2bd/2ba

9.8 out of 10, Exceptional, (32)
"Highly recommend! Great location. Beautiful view. Responsive owner. "
Downtown Park VIEWS Mich Ave, Museums 2bd/2ba
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
Furniture,Couch,Table,Rug,Coffee Table

Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover

9.6 out of 10, Exceptional, (18)
"My daughter and I had a girls weekend in Chicago and loved the location and neighborhood. The property was updated and clean yet maintained the flavor of city living."
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
Downtown Penthouse Huge Patio with Great View
Living area

Downtown Penthouse Huge Patio with Great View

2.0 star property
Downtown Penthouse Huge Patio with Great View
The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown
Dining

The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown

9.8 out of 10, Exceptional, (26)
"Great location and nice accommodations. I would recommend but one thing to be aware of are the wooden floors, which is charming, but are squeaky."
The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown
Chic Urban Retreat Near Wrigley Field w/Parking
Private kitchen

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (9)
"Clean, comfortable, professional, smooth and helpful transactions. A wonderful place I look forward to returning to very soon. "
The price is AED 367
AED 1,398 total
includes taxes & fees
24 Feb - 25 Feb
Chic Urban Retreat Near Wrigley Field w/Parking
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
Pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (682)
"This is a great hotel. The rooms have a kitchenette and the staff is wonderful! Beautiful hotel, great amenities. "
The price is AED 403
AED 581 total
includes taxes & fees
25 Feb - 26 Feb
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (433)
"Loved the app and process for checking-in and out. The property itself could use some TLC, there were lots of scuff marks and scratches in the walls due to prior tenants. Our unit could have used a painting. There also wasn't a space to get extra toiletries per the app, would take this out if it's not really an option. "
The price is AED 349
AED 409 total
includes taxes & fees
23 Mar - 24 Mar
Sonder South Wabash
Found Chicago powered by Sonder
Room

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is AED 493
AED 578 total
includes taxes & fees
5 Mar - 6 Mar
Found Chicago powered by Sonder
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

How much do condos in Winnetka cost?
Prepare to pay from AED 367 to AED 1,759 per night for condos in Winnetka. No matter your budget, an ideal stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winnetka?
Winnetka has 200 condos. To help you find a place that’s right for you, use our filters to search for the must-have hotel conveniences.
Why book your condo in Winnetka with Expedia?
Reserving a condo in Winnetka is as easy as entering your travel dates and selecting a place that suits your style. Seeking something luxurious or affordable, or a property that also has a pool and a hot tub? Use Expedia’s search filters to narrow your results even further and find the perfect fit.
How can I find cheap condos in Winnetka?
The best way to get cheap condos in Winnetka is with Expedia’s easy-to-use filter tool. Refine your search by budget, amenities and star rating to access unbeatable bargains in just a few keystrokes.