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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Winnetka condo rentals

Exterior detail
Chic Urban Retreat Near Wrigley Field w/Parking

Condo in Lakeview

Chic Urban Retreat Near Wrigley Field w/Parking
10.0 out of 10, Exceptional, (44)
"Great spot in a wonderful location!"
United States
Jasson R.
The price is AED 551
AED 1,663 total
includes taxes & fees
2 Jan - 3 January 2026
Chic Urban Retreat Near Wrigley Field w/Parking
Fridge, microwave, oven, stovetop
Chic Suite/Mins to L Train /Laundry/Free Parking

Condo in Oak Park

Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (57)
"Super convenient if you want to see the Frank Lloyd wright house - walked to studio and train and great cafes. Perfect location "
United States
Travis S.
The price is AED 236
AED 712 total
includes taxes & fees
6 Jan - 7 January 2026
Chic Suite/Mins to L Train /Laundry/Free Parking
Private kitchen
Wrigley Field MVP Suite 1 Bedroom Apartment

Condo in Lakeview

Wrigley Field MVP Suite 1 Bedroom Apartment
9.6 out of 10, Exceptional, (14)
"Great location. 30 steps to Wrigley field. Clean. Safe. Very clean apt."
United States
Curt M.
The price is AED 657
AED 2,466 total
includes taxes & fees
2 Jan - 3 January 2026
Wrigley Field MVP Suite 1 Bedroom Apartment
Exterior
1 Bedroom | Free Breakfast Buffet, Indoor Pool

Condo in Glenview

1 Bedroom | Free Breakfast Buffet, Indoor Pool
2.0 star property
The price is AED 507
AED 651 total
includes taxes & fees
2 Jan - 3 January 2026
1 Bedroom | Free Breakfast Buffet, Indoor Pool
Exterior
1 Bedroom | Free Breakfast, Indoor Pool Access

Condo in Half Day

1 Bedroom | Free Breakfast, Indoor Pool Access
The price is AED 491
AED 623 total
includes taxes & fees
16 Jan - 17 January 2026
1 Bedroom | Free Breakfast, Indoor Pool Access
Fridge, microwave, oven, stovetop
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

Condo in South Evanston

MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.6 out of 10, Exceptional, (25)
"Good place to stay, comfortable and quiet."
United States
Andrew N.
The price is AED 1,149
AED 2,295 total
includes taxes & fees
2 Jan - 3 January 2026
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Exterior
Wrigley Field All Star Suite 3 Bedrooms 2 Bath

Condo in Lakeview

Wrigley Field All Star Suite 3 Bedrooms 2 Bath
9.4 out of 10, Exceptional, (22)
"Everything was excellent. Highly recommended!!!"
United States
Donald S.
The price is AED 1,392
AED 3,481 total
includes taxes & fees
2 Jan - 3 January 2026
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Private kitchen
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Condo in Lakeview

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
9.6 out of 10, Exceptional, (27)
"The location was amazing! Comfortable beds and easy access. "
United States
Donald N.
The price is AED 1,759
AED 4,034 total
includes taxes & fees
2 Jan - 3 January 2026
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Private kitchen
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms

Condo in Lakeview

Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
9.0 out of 10, Wonderful, (15)
"The apartment is literally across the street from the ballpark. Very clean, easy to check in, big space, everything we needed was there, couldn't have asked for more."
United States
vince h.
The price is AED 1,759
AED 4,034 total
includes taxes & fees
2 Jan - 3 January 2026
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Private kitchen
Wrigley Field Home Run 4 Bedroom, 2 Bathroom

Condo in Lakeview

Wrigley Field Home Run 4 Bedroom, 2 Bathroom
9.6 out of 10, Exceptional, (19)
"Would definitely stay there again "
United States
Enrique
The price is AED 1,759
AED 4,034 total
includes taxes & fees
2 Jan - 3 January 2026
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Private kitchen
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Condo in Lakeview

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
10.0 out of 10, Exceptional, (22)
"Perfect for a small group attending a Wrigley event. Very comfortable beds. Very open great room with view of the stadium across the street. Would absolutely rent again."
United States
Anonymous traveler
The price is AED 1,759
AED 4,034 total
includes taxes & fees
2 Jan - 3 January 2026
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Staff are really nice and responsible for all the things, clean and big room"
Sumin 3-night trip
Posted 8 hours ago
Hyatt Regency Chicago

Frequently asked questions

How much do condos in Winnetka cost?
Condos in Winnetka range from AED 623 to AED 4,034 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 242 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.
How can I find cheap condos in Winnetka?
The best way to locate cheap condos in Winnetka is with Expedia's nifty filter tool. Fine-tune your search results by amenities, budget and star rating to secure unbeatable rates in a couple of clicks.