Find Extended Stay Hotels in Winnetka, IL

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Top Winnetka Extended Stay Hotels | Reserve now, pay later

River Hotel
4.0 star property
8.8 out of 10, Excellent, (4750)
"Staff friendly and helpful..and accommodations just right..great location! "
Adrienne
$123 nightly
The price is $144
Nov 11 - Nov 12
Total with taxes and fees
River Hotel
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very Good, (278)
"Perfect location! Tons of restaurants and shopping nearby! "
MaryJane
$76 nightly
The price is $89
Nov 10 - Nov 11
Total with taxes and fees
FOUND Hotel Chicago River North
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.8 out of 10, Excellent, (3356)
"Great location, nice rooms"
David
$122 nightly
The price is $144
Nov 16 - Nov 17
Total with taxes and fees
Club Quarters Hotel, Central Loop, Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very Good, (4092)
"Clean room , staff were friendly, a lot of restaurants in the area."
Carmen
$139 nightly
The price is $164
Nov 11 - Nov 12
Total with taxes and fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
8.4 out of 10, Very Good, (2197)
"Very clean accommodations and great customer service from the staff!!"
Steve
$121 nightly
The price is $142
Nov 9 - Nov 10
Total with taxes and fees
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Loews Chicago Hotel
4.5 star property
9.4 out of 10, Exceptional, (1569)
"Great stay, comfy beds!"
Brea
$256 nightly
The price is $301
Oct 24 - Oct 25
Total with taxes and fees
Loews Chicago Hotel
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (959)
"Great location and cleanliness of rooms. Staff was extremely helpful "
Amy
$160 nightly
The price is $188
Nov 10 - Nov 11
Total with taxes and fees
Sentral Michigan Avenue
Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
8.8 out of 10, Excellent, (2087)
"Beautiful place loved everything about this hotel"
Joel
$131 nightly
The price is $154
Nov 11 - Nov 12
Total with taxes and fees
Homewood Suites by Hilton Chicago Downtown South Loop
Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
8.4 out of 10, Very Good, (1015)
"Excellent staff, very helpful and welcoming."
Shane
$140 nightly
The price is $165
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn & Suites Chicago - Downtown by IHG
theWit Chicago, a Hilton Hotel
4.5 star property
9.0 out of 10, Wonderful, (1013)
"Really great location. Accessible to train lines, shopping area close by, plenty of places nearby to eat. Hotel was great and clean. "
Andrea
$237 nightly
The price is $278
Nov 9 - Nov 10
Total with taxes and fees
theWit Chicago, a Hilton Hotel
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.

Find out more about Winnetka

Discover top Winnetka attractions

Winnetka, Illinois, offers an enticing blend of charm and adventure for the discerning traveler. Begin your exploration at the stunning Lighthouse Beach, where families can relax on the sandy shores, enjoy a picnic, or take a dip in Lake Michigan’s refreshing waters. Next, immerse yourself in local history at the Winnetka Historical Society, housed in a charming Victorian home, where you can learn about the area’s rich heritage through engaging exhibits. For a delightful shopping experience, stroll down Elm Street, dotted with boutique shops and artisanal cafes that cater to every taste. Families will appreciate the lush greenery of Crow Island Woods, an expansive nature preserve with trails perfect for hiking and bird-watching. Finally, don’t miss the opportunity to indulge your taste buds at local favorite, The Grille on Laurel, known for its seasonal menu and inviting atmosphere. For accommodations, consider staying in the heart of downtown Winnetka, where you’ll find boutique hotels offering personalized service and easy access to all these local treasures. After a day of exploration, unwind in luxurious surroundings that make you feel pampered and appreciated.

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Most booked related extended stays in Winnetka in 2025

Frequently asked questions

Why book an extended stay hotel in Winnetka through Expedia?
From our special offers to our rewards programs, you'll save big bucks when you reserve your extended stay in Winnetka through Expedia. Enter your travel dates to view our long-term rentals, then narrow your search using the filters to find your ideal pad. Our extended stay hotels in Winnetka come with amenities like kitchens, gyms and recreational facilities to help make your long-term stay more comfortable. Whether you're seeking a hotel for a few days or somewhere with excellent weekly rates, Expedia will help you find your dream getaway.
What can I expect from an extended stay hotel?
With amenities such as kitchens, dining areas and laundries, extended stay hotels in Winnetka can be a comfortable and cost-effective alternative to standard accommodations. Make home-cooked meals and save on laundry services. Sometimes offering discounted weekly rates, extended stay hotels range from simple studios to spacious options with several bedrooms. They also have many of the amenities you'd find in a standard hotel, like recreational facilities or 24/7 guest services. If you're looking for flexibility, privacy and a comfortable retreat for a while, an extended stay hotel is an excellent choice.

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