Search Condos Rentals in Winnetka from CA $173

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Browse Select Winnetka Condo Rentals

Historic Gold Coast Condo - Half Block From Beach & Major Attractions

Historic Gold Coast Condo - Half Block From Beach & Major Attractions

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (166)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK

Cozy 3BR on Chicago's North Side & Free Parking On-premises!

10.0 out of 10, Exceptional, (1)
"Rogers Park is a richly diverse and fascinating neighborhood and this place gives great access to what the neighborhood has to offer. It has good transportation to the rest of the north side and downtown. Expect urban funky and fun. "
Cozy 3BR on Chicago's North Side & Free Parking On-premises!

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (35)
"Fantastic! Great location, parking spot available, very clean! "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

Wrigleyville Inn AllStar Unit

9.4 out of 10, Exceptional, (18)
"Enjoyed a dinner party with friends Place was perfect Management helpful "
The price is CA $521
CA $1,287 total
includes taxes & fees
Jun 29 - Jun 30
Wrigleyville Inn AllStar Unit

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (70)
"We had a great stay at the rental. Stacy was an amazing host. We would definitely stay there again. "
Classic Lincoln Park 2 bedroom condo- parking included

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (201)
"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,

10 min walk to Stevenson Convention Center

8.4 out of 10, Very good, (6)
"Very good location and clean. "
10 min walk to Stevenson Convention Center

Guild #1 | Gold Coast Mag Mile Best Location

9.8 out of 10, Exceptional, (46)
"My friend and our kids rented this place for a long weekend in Chicago. The property is great, in a fabulous location, and the owners are so kind and easy to get in touch with."
Guild #1 | Gold Coast Mag Mile Best Location

MICH AVE #23 2bd/2ba Downtown, Museums w/ Views

9.6 out of 10, Exceptional, (22)
"We thoroughly enjoyed our stay here. The condo was clean, the beds were comfortable and everything we needed was available. The owners were very communicative, friendly and helpful. The view was amazing, especially at sunset. "
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views

Urban Chicago Escape ~ 1 Mi to Local Beaches!

9.4 out of 10, Exceptional, (17)
"The place was clean and fit our needs. Great location near the lake and close to the train stop."
Urban Chicago Escape ~ 1 Mi to Local Beaches!

Huge Projector and Designated Workspace - Near Wrigley!

The price is CA $173
CA $508 total
includes taxes & fees
Jul 14 - Jul 15
Huge Projector and Designated Workspace - Near Wrigley!

Entire 2 bedroom with Office & Deck!

9.2 out of 10, Wonderful, (11)
"Good stay"
Entire 2 bedroom with Office & Deck!

Spacious 3-bedroom, 2-bath condo, free parking/Oak Park

9.0 out of 10, Wonderful, (29)
"It was nice"
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (18)
"This spacious condo was perfect for our family of 7. Having a parking spot was a huge help and the location was incredibly convenient for use of public transport throughout our stay. We'd definitely stay there again!"
Gorgeous 3BR River North Condo - Free Parking

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (13)
"Place was perfect, clean and comfortable. Location is fantastic!"
Spacious, Clean and Steps from Wrigley Field!

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

9.6 out of 10, Exceptional, (26)
"Everything was good and it was in a great location. Renters were kind and frequently checked in. "
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!

9.6 out of 10, Exceptional, (22)
"The whole trip was so awesome but the room was so perfect. Being lifelong Cubs fans it was amazing to open the blinds and see wrigley field right there. Thank you so much for letting us have early arrival. It really was needed. We will check on using this property in the future."
The price is CA $658
CA $1,473 total
includes taxes & fees
Jul 7 - Jul 8
Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!

Downtown Mich Ave #7| Park View Penthouse +gym

10.0 out of 10, Exceptional, (5)
"Great location...host quick response..."
Downtown Mich Ave #7| Park View Penthouse +gym

Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago

10.0 out of 10, Exceptional, (24)
"Awesome stay!"
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to 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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Frequently asked questions

How much do condos in Winnetka cost?
Condos in Winnetka range from CA $173 to CA $658 per night. This will give you lots of room for your entire crew at a price that won't stretch the budget. 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?
Choose from 229 condos in Winnetka. Whether you're traveling with the family or organizing a weekend break with your buddies, Expedia can help you find the right space for your whole crew.
Why book your condo in Winnetka with Expedia?
Expedia will help you find your ideal condo in Winnetka. After a luxury escape? Make the most of our filters to search for properties that have a 5-star rating. If you're sticking to a budget, select how much you want to spend and then browse our fabulous options. We'll help you find the right place whatever your vacation looks like.