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Oct 4 - Oct 5
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Featured Winnetka 5 Stars Hotels

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
15.52 mi from city center
$144 nightly
The price is $170 total per night
$170 total
Nov 3 - Nov 4
Total with taxes and fees
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a business center, express check-out, and a porter/bellhop.
Pet friendly
Free WiFi
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
15.79 mi from city center
$113 nightly
The price is $133 total per night
$133 total
Nov 3 - Nov 4
Total with taxes and fees
At Warwick Allerton - Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 72 per day. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this family-friendly hotel include a conference center, a 24-hour business center, and a computer station.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
15.86 mi from city center
$174 nightly
The price is $205 total per night
$205 total
Nov 4 - Nov 5
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
15.89 mi from city center
$112 nightly
The price is $132 total per night
$132 total
Nov 4 - Nov 5
Total with taxes and fees
Guests of Freehand Chicago enjoy features like a 24-hour gym, free WiFi in public areas, and express check-in. Self parking is offered for USD 49 per night. Multilingual staff at the 24-hour front desk can assist with tours or tickets, dry cleaning/laundry, and luggage storage. Additional amenities include express check-out, laundry facilities, and a fireplace in the lobby.
Pet friendly
Free WiFi
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
15.94 mi from city center
$179 nightly
The price is $210 total per night
$210 total
Oct 19 - Oct 20
Total with taxes and fees
Guests staying at Hilton Garden Inn Chicago Downtown/Magnificent Mile enjoy an indoor pool, a gym, and free WiFi in public areas. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Additional amenities include meeting rooms, express check-out, and a porter/bellhop.
Pool
Pet friendly
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
16.04 mi from city center
$301 nightly
The price is $348 total per night
$348 total
Oct 30 - Oct 31
Total with taxes and fees
At InterContinental Chicago Magnificent Mile by IHG, guests enjoy an indoor pool, a gym, and a steam room. Valet parking is offered for USD 88 per day. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and securing valuables. Other amenities at this luxury hotel include free WiFi in public areas, express check-out, and a reception hall.
Pool
Spa
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
16.29 mi from city center
$173 nightly
The price is $204 total per night
$204 total
Nov 4 - Nov 5
Total with taxes and fees
At citizenM Chicago Downtown, guests have access to a gym, free WiFi in public areas, and a 24-hour business center. The 24-hour front desk has staff standing by to help with securing valuables and luggage storage. Additional amenities include coffee/tea in a common area, a computer station, and express check-in.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
16.31 mi from city center
$176 nightly
The price is $207 total per night
$207 total
Nov 2 - Nov 3
Total with taxes and fees
Guests of The Allegro Royal Sonesta Hotel Chicago Loop enjoy a 24-hour gym, WiFi in public areas, and conference space. Valet parking is offered for USD 77 per night. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a ballroom, a fireplace in the lobby, and an ATM.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
17.07 mi from city center
$145 nightly
The price is $170 total per night
$170 total
Nov 2 - Nov 3
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
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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.

Best 5 star hotels in Winnetka

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Winnetka. After all, treating yourself to the finer things is what vacations are about. 

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Winnetka hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Winnetka 5 star hotels and resorts typically offer luxury amenities such as:

  • Gourmet restaurant
  • Full-service fitness center with pool
  • Luxury spa 
  • Welcome gifts upon arrival
  • Top-of-the-line beds and linens 
  • Designer personal care products
  • Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Winnetka with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place: 

  • Search hotels by price, ranging from $132 to $348
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 4,402 5 star hotels in Winnetka!

Winnetka hotels essential information

Accommodation
4,402 hotels
Lowest Price
$132
Highest Price
$348
Popular hotels
Congress Plaza Hotel, Freehand Chicago, Embassy Suites by Hilton Chicago Downtown River North, Hilton Chicago/Magnificent Mile Suites, Hilton Garden Inn Chicago Downtown/Magnificent Mile, InterContinental Chicago Magnificent Mile by IHG, citizenM Chicago Downtown, The Allegro Royal Sonesta Hotel Chicago Loop, Warwick Allerton - Chicago

Recent Reviews

Freehand Chicago

Freehand Chicago

5/5 Excellent
"(Private queen room) the room was small but very comfortable. Everyone was very nice and friendly. Would absolutely stay again. "
A verified traveler stayed at Freehand Chicago
Posted 3 days ago
Freehand Chicago

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