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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 1782 Apartments in Winnetka with updated reviews, rates, and availability.

Cozy studio in Andersonville Chicago
Iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.6 out of 10, Exceptional, (5)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is AED 239
AED 512 total
includes taxes & fees
9 Jun - 10 Jun
Cozy studio in Andersonville Chicago
Luxurious 3 Bedroom Apartment in Chicago
Microwave, oven, stovetop, dishwasher

Luxurious 3 Bedroom Apartment in Chicago

9.6 out of 10, Exceptional, (4)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (19)
"This place was perfect for our overnight stay in Chicago! Thank you to the owners for making everything super easy and smooth. "
The price is AED 426
AED 1,098 total
includes taxes & fees
9 Jun - 10 Jun
2-bedroom apartment just 2 minutes drive to Wrigley Field
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Fridge, microwave, oven, stovetop

Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!

9.2 out of 10, Wonderful, (21)
"The stay was amazing I enjoyed myself "
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Exterior

North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

10.0 out of 10, Exceptional, (106)
"Really enjoyed our stay. Parking was easy and we could walk to restaurants. Felt very safe and the neighborhood was welcoming. Would stay again."
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (53)
"This property was clean, and the host provided clear instructions for access. I reached out to the host/owner and they were immediately responsive. Overall a great experience."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (22)
"This place was perfect for us, and right where we needed it to be. "
Charming Wrigleyville Home Close to the Cubs!
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Fridge, microwave, oven, stovetop

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

10.0 out of 10, Exceptional, (111)
"Fantastic location and wonderful stay. The host was wonderful and great communication. Highly recommend staying here for a Chicago visit!!!"
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (23)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is AED 389
AED 999 total
includes taxes & fees
16 Jun - 17 Jun
Bright Garden Studio
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
3 bedrooms, WiFi, bed sheets

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

9.0 out of 10, Wonderful, (88)
"Nice property, enjoyed the stay."
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Luxury Loft Collection 703 - Terrace - River North
Property grounds

Luxury Loft Collection 703 - Terrace - River North

2.0 star property
9.8 out of 10, Exceptional, (10)
"This property was perfect for our mother-daughter weekend. It was clean, a great location, and just the space we needed to play games, watch a movie, eat together, and sleep well."
Luxury Loft Collection 703 - Terrace - River North
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Cozy, Comfortable and Convenient apartment. Close to everything!
Smart TV, books

Cozy, Comfortable and Convenient apartment. Close to everything!

9.8 out of 10, Exceptional, (63)
"Amazing place and clean"
The price is AED 533
AED 1,200 total
includes taxes & fees
24 Jun - 25 Jun
Cozy, Comfortable and Convenient apartment. Close to everything!
Spacious loft in the heart of West Town, Noble Square Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Spacious loft in the heart of West Town, Noble Square Chicago

10.0 out of 10, Exceptional, (4)
"We recommend this listing."
Spacious loft in the heart of West Town, Noble Square Chicago
New Garden Studio near Wrigley/DePaul/Dwtn
Miscellaneous

New Garden Studio near Wrigley/DePaul/Dwtn

9.4 out of 10, Exceptional, (13)
"We had a great stay. Very clean and spacious, well supplied kitchen that we were able to use to make meals. Fantastic communication with management. Absolutely will stay again. Easy walk to coffee, restaurants and transportation. Thank you!"
New Garden Studio near Wrigley/DePaul/Dwtn
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Fridge, microwave, oven, stovetop

Perfect 4 Bedroom/3 Bath in the HEART of Old Town

10.0 out of 10, Exceptional, (60)
"Fantastic location in Old Town. Very spacious rental, check-in was easy, would definitely stay again and recommend!! "
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Chic 1-bedroom apartment,15mims from downtown
Living area

Chic 1-bedroom apartment,15mims from downtown

10.0 out of 10, Exceptional, (1)
"Stayed here to work C2E2 for the weekend. Great big space with everything I needed to rest up after a long day of work."
Chic 1-bedroom apartment,15mims from downtown
Bright & Modern Apt | Steps to Lake, Train, Food
Fridge, microwave, oven, stovetop

Bright & Modern Apt | Steps to Lake, Train, Food

10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised with easy (albeit somewhat tight) parking, minimal house rules and clean-up required, and a reasonable price. I would gladly stay again on a future trip to Chicago."
The price is AED 657
AED 1,204 total
includes taxes & fees
16 Jun - 17 Jun
Bright & Modern Apt | Steps to Lake, Train, Food
Serene 3-bedroom apartment in Chicago
Smart TV

Serene 3-bedroom apartment in Chicago

10.0 out of 10, Exceptional, (2)
"I wish we had stayed longer!"
Serene 3-bedroom apartment in Chicago
Animal House Near Sox Stadium
Terrace/patio

Animal House Near Sox Stadium

9.4 out of 10, Exceptional, (3)
"We had a very nice time with no issues! We would absolutely stay here again."
Animal House Near Sox Stadium
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

What's it like to stay at an apartment in Winnetka?
There are plenty of places to stay with in the Chicago area, with 5256 lodging choices including 2614 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.