Apartments in Winnetka for Rent

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Our top choices for Winnetka apartments

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"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
$149 nightly
The price is $166
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sleek 1BR Apt w/ Laundry

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
West Loop Living – Bright 1BR

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
2.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
$325 nightly
The price is $366
Dec 29 - Dec 30
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stylish 1BR in West Loop

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"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.
$153 nightly
The price is $168
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sun-Drenched 1BR Apartment

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
2.0 star property
Downtown Chicago
$308 nightly
The price is $345
Jan 4 - Jan 5, 2026
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 3

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
$288 nightly
The price is $320
Jan 8 - Jan 9, 2026
Total with taxes and fees
South Loop Rooftop With In & Out Parking 1

Your Chicago get Away

Your Chicago get Away
Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
$358 nightly
The price is $387
Dec 15 - Dec 16
Total with taxes and fees
Your Chicago get Away

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
$187 nightly
The price is $206
Dec 16 - Dec 17
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
$328 nightly
The price is $370
Dec 22 - Dec 23
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Complete 1BR Home Sum

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
$343 nightly
The price is $388
Dec 18 - Dec 19
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
$363 nightly
The price is $413
Dec 30 - Dec 31
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2

Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING
Near West Side
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
$271 nightly
The price is $334
Dec 16 - Dec 17
Total with taxes and fees
Spacious 3-bedroom apartment near downtown, FREE PARKING

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
2.0 star property
Lawndale
8.0 out of 10, Very Good, (2)
"While it was a great price, you get what you pay for. "
United States
Deya R.
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
2.0 star property
Downtown Chicago
$339 nightly
The price is $383
Dec 23 - Dec 24
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 5

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
Cozy Boho Chicago - 10 Minutes to Downtown 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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Top Winnetka Hotel Reviews

Find out more about Winnetka

Winnetka Apartments information

Number of reviews
63
Accommodation
2241 Apartments
Lowest Price
$166
Highest Price
$413

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 5612 lodging choices including 1709 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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