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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winnetka apartments

Terrace/patio

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (57 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is AED 555
AED 1,157 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Terrace/patio

2. Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
South Evanston
10.0 out of 10, Exceptional, (9 reviews)
"It was a great experience! Very nice and clean place. Advertised exactly as seen. Parking was very easy and the location was great. Overall, would definitely stay again!"
United States
Sophia P.
The price is AED 430
AED 993 total
includes taxes & fees
18 Oct - 19 Oct
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
Exterior detail

3. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (288 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
The price is AED 255
AED 307 total
includes taxes & fees
23 Sep - 24 Sep
King Bed Non-Smoking
Interior

4. 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 AED 309
AED 658 total
includes taxes & fees
18 Oct - 19 Oct
Stunning & Stylish Downtown Studio - Highland Park
Interior

5. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
Downtown Evanston
9.8 out of 10, Exceptional, (39 reviews)
"This is by far the best experience I’ve had with Abnbs! The place was as advertised, the host was very friendly, prompt and accommodating. "
United States
Brian W.
The price is AED 676
AED 1,347 total
includes taxes & fees
22 Sep - 23 Sep
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
TV, offices

6. Charming 1BR Apt in Evanston

Charming 1BR Apt in Evanston
South Evanston
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful rooms with hardwood floors and lots of natural light. Close to fun coffee shops and restaurants. Overall a great place to stay when you're in Evanston!"
United States
Kim B.
The price is AED 316
AED 917 total
includes taxes & fees
23 Sep - 24 Sep
Charming 1BR Apt in Evanston
TV, offices

7. Perfectly Located 1-Bedroom Unit

Perfectly Located 1-Bedroom Unit
South Evanston
10.0 out of 10, Exceptional, (4 reviews)
"The apartment was very clean and the bed was super comfortable. We slept great. We didn’t spend much time at the apartment but for our trip it was exactly what we needed. "
United States
V S.
The price is AED 338
AED 943 total
includes taxes & fees
12 Oct - 13 Oct
Perfectly Located 1-Bedroom Unit
1 bedroom, iron/ironing board, WiFi (free), bed sheets

8. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (97 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
The price is AED 281
AED 573 total
includes taxes & fees
5 Oct - 6 Oct
Cozy studio in Andersonville Chicago
Exterior detail

9. Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
7.4 out of 10, Good, (6 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is AED 220
AED 545 total
includes taxes & fees
22 Sep - 23 Sep
Chic Studio in Downtown Highland Park near Metra
1 bedroom, iron/ironing board, WiFi (free), bed sheets

10. Chic Studio - In Downtown Highland Park, by Metra

Chic Studio - In Downtown Highland Park, by Metra
Highland Park
8.4 out of 10, Very good, (16 reviews)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
United States
Deborah
The price is AED 327
AED 638 total
includes taxes & fees
5 Oct - 6 Oct
Chic Studio - In Downtown Highland Park, by Metra
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

11. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (25 reviews)
"We had a great time it was an awesome place and we would definitely stay there again! The host was great the place was well equipped and in a great location for us!!"
United States
Wendy T.
The price is AED 433
AED 1,496 total
includes taxes & fees
22 Sep - 23 Sep
The Lincoln Square Hideaway
Dining

12. "Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (17 reviews)
"Great spot to stay in Evanston, definitely recommend!"
United States
Surath G.
The price is AED 779
AED 1,515 total
includes taxes & fees
27 Sep - 28 Sep
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
1 bedroom, desk, iron/ironing board, WiFi

13. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.4 out of 10, Very good, (10 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is AED 322
AED 872 total
includes taxes & fees
28 Sep - 29 Sep
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Dining

14. Walk to the Beach • Private Office • 5BR

Walk to the Beach • Private Office • 5BR
Rogers Park
8.0 out of 10, Very good, (13 reviews)
"This 5-bedroom Chicago apartment was an exceptional find for our group, offering a rare combination of ample space, safety, and convenience. The location is incredibly walkable and just a short distance from the beach, which made for wonderful morning walks and beautiful views. The neighborhood has a vibrant, welcoming atmosphere with a large student population, giving the area a lively yet entirely safe energy. One of the biggest highlights was the excellent, hassle-free parking, which is an...
United States
Joanna K.
The price is AED 344
AED 1,911 total
includes taxes & fees
23 Sep - 24 Sep
Walk to the Beach • Private Office • 5BR
Microwave, oven, stovetop

15. Chic apartment with fitness room and AC in beautiful Chicago

Chic apartment with fitness room and AC in beautiful Chicago
Rogers Park
6.4 out of 10, (7 reviews)
"Everything was smooth and efficient "
United States
Brande M.
The price is AED 551
AED 1,382 total
includes taxes & fees
22 Sep - 23 Sep
Chic apartment with fitness room and AC in beautiful Chicago
Property grounds

16. 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
9.8 out of 10, Exceptional, (102 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
The price is AED 467
AED 1,179 total
includes taxes & fees
27 Sep - 28 Sep
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
TV

17. Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.8 out of 10, Exceptional, (7 reviews)
"Great stay for a family weekend - we were within easy uber distance of our family and downtown - where we went to watch the Chicago marathon."
United States
Surya B.
The price is AED 613
AED 1,240 total
includes taxes & fees
20 Oct - 21 Oct
Relaxing 3BR Getaway Close to Dining & Shopping
Room

18. Cozy 1-Bedroom Apartment

Cozy 1-Bedroom Apartment
Portage Park
Cozy 1-Bedroom Apartment
Smart TV, computer monitors

19. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (5 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
The price is AED 318
AED 1,704 total
includes taxes & fees
22 Sep - 23 Sep
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
TV

20. 2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
The price is AED 240
AED 1,356 total
includes taxes & fees
14 Oct - 15 Oct
2BR • Newly Furnished Modern Apt • Near O'Hare
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 Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Great location"
SEAN 1-night trip
Posted 5 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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 5411 lodging choices including 1749 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's a favorite apartment for a stay in Winnetka?
Below are some of the top apartments in the area: Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley: Located in Chicago, 11 mi/17.7 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Bella Villa on Taylor Street Chicago's Little Italy 1 mile west the Loop & UIC: Located 16.9 mi/27.2 km away in Chicago. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. King Bed Non-Smoking: It's located in Des Plaines, 8.9 mi/14.3 km from Winnetka. Includes Smart TVs.
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 get outside and enjoy nature. Wrigley Field and Navy Pier 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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