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Oct 29 - Oct 30
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Oct 30 - Oct 31
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Oct 31 - Nov 2
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Nov 7 - Nov 9

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Compare 4,481 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3078)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is ￥16,434
￥19,292 total
includes taxes & fees
Nov 27 - Nov 28
Eurostars Magnificent Mile
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2115)
"Great stay "
United States
Melinda
The price is ￥15,704
￥18,435 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4759)
"Great area at a good price. "
United States
Laura
The price is ￥14,651
￥17,200 total
includes taxes & fees
Nov 23 - Nov 24
River Hotel
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2867)
"Had a great stay!"
United States
Josh
The price is ￥16,434
￥19,292 total
includes taxes & fees
Nov 23 - Nov 24
Aloft Chicago Mag Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2229)
"Rooms were clean with a great view of the lake and the city "
United States
Nathan
The price is ￥14,824
￥22,581 total
includes taxes & fees
Nov 25 - Nov 26
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (4019)
"Great place to stay. "
United States
sherry
The price is ￥16,684
￥19,587 total
includes taxes & fees
Oct 30 - Oct 31
citizenM Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
9.0 out of 10, Wonderful, (3195)
"Overall it was a great place to stay."
United States
Edward
The price is ￥16,748
￥19,660 total
includes taxes & fees
Nov 16 - Nov 17
Hilton Chicago/Magnificent Mile Suites
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very Good, (2269)
"Staff was wonderful, property was clean and welcoming. Great amenities for families and great location."
United States
Stephen
The price is ￥17,274
￥24,744 total
includes taxes & fees
Nov 24 - Nov 25
Hilton Chicago
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very Good, (2534)
"Very accessible location and amazing staff. "
United States
Fatima
The price is ￥10,239
￥14,700 total
includes taxes & fees
Nov 11 - Nov 12
Freehand Chicago
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very Good, (9616)
"Area is great and walkable distance to touring areas. "
United States
Alejandro
The price is ￥25,884
￥30,385 total
includes taxes & fees
Nov 2 - Nov 3
Congress Plaza Hotel
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very Good, (4123)
"This hotel had a great location to shopping and several enjoyable restaurants."
United States
laura
The price is ￥17,657
￥20,727 total
includes taxes & fees
Nov 25 - Nov 26
Hilton Garden Inn Chicago Downtown/Magnificent Mile
American cuisine
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1633)
"Staff was friendly upon check in and the premise was very clean."
United States
Kelan
The price is ￥15,521
￥18,220 total
includes taxes & fees
Nov 26 - Nov 27
Crowne Plaza Chicago West Loop by IHG
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1004)
"Great stay"
Australia
Bart
The price is ￥15,392
￥18,070 total
includes taxes & fees
Nov 9 - Nov 10
Best Western River North Hotel
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2679)
"Great place to stay "
United States
Larry William
The price is ￥16,415
￥23,573 total
includes taxes & fees
Nov 25 - Nov 26
Hotel Riu Plaza Chicago
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very Good, (292)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is ￥11,579
￥13,594 total
includes taxes & fees
Nov 10 - Nov 11
FOUND Hotel Chicago River North
Lobby
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (2026)
"Great place to stay "
United States
Cheryl
Silversmith Hotel Chicago Downtown
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG
voco Chicago Downtown - Riverwalk by IHG
3.5 star property
8.8 out of 10, Excellent, (3283)
"Great stay "
United States
shanae
The price is ￥19,781
￥23,221 total
includes taxes & fees
Nov 23 - Nov 24
voco Chicago Downtown - Riverwalk by IHG
Rooftop terrace
Hyatt Centric The Loop Chicago
Hyatt Centric The Loop Chicago
4.0 star property
9.0 out of 10, Wonderful, (2222)
"Beautiful hotel "
United States
Abigail
The price is ￥18,819
￥22,094 total
includes taxes & fees
Nov 25 - Nov 26
Hyatt Centric The Loop Chicago
Exterior
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
8.6 out of 10, Excellent, (2586)
"Very nice for price and location"
United States
Deborah
The price is ￥14,928
￥20,205 total
includes taxes & fees
Nov 23 - Nov 24
La Quinta Inn & Suites by Wyndham Chicago Downtown
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.2 out of 10, Very Good, (3661)
"Excellent location, old style hotel with an independent feel. "
United States
Jose
The price is ￥12,957
￥15,209 total
includes taxes & fees
Nov 24 - Nov 25
The Whitehall Hotel, BW Premier Collection
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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Stay near popular Winnetka attractions

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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Elder Lane Beach

This lakefront sanctuary offers a serene escape with pristine sandy shores and Lake Michigan views. Enjoy a peaceful afternoon in the adjacent park with its well-maintained picnic areas and playground.
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Learn more about Winnetka

Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theater.

See all hotels in Winnetka
Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Top Winnetka Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"Excellent place to stay. Easy access to “L” train. In the middle of all the musical theatres. Soldier Field and Navy Pier are walking distance from the hotel."
Mark Tavis 2-night trip
Posted 10 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop

More cheap stays in Winnetka

Motel 6 Schiller Park, IL - Chicago O'Hare

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue, I-90 at Kennedy Expwy, Exit 79-A S., Schiller Park, IL
The price is ￥8,216 per night from Nov 11 to Nov 12
￥8,216
￥9,365 total
Nov 11 - Nov 12
includes taxes & fees
6.4/10 (1,800 reviews)

Frequently asked questions

What's the best place to stay in Winnetka?
Located 15.9 mi (25.5 km) from the heart of Winnetka, Embassy Suites by Hilton Chicago Downtown River North is a top choice for your stay based on our traveler data. Two other options for your visit to the area are Congress Plaza Hotel and Freehand Chicago. See all available top hotels, or vacation rentals in Winnetka.
What are some of the best vacation home rentals that Winnetka has to offer?
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: Visitors like this Winnetka vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. See all vacation rentals in Winnetka.
If I need to cancel my hotel reservation in Winnetka, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winnetka.
Where can I learn more about changing or cancelling my trip to Winnetka?
For additional details about rescheduling or cancelling your trip to Winnetka, click here.
What's the best place to stay close to Elder Lane Beach?
DoubleTree by Hilton Chicago - North Shore Conference Center is one of the top choices for your stay based on our traveler data, and this 4-star hotel offers a restaurant and an outdoor pool. It's located 3.5 mi (5.6 km) from Elder Lane Beach. Other good options within 5 miles include Hampton Inn & Suites Chicago-North Shore/Skokie and Residence Inn by Marriott Chicago Wilmette/Skokie.
What's the best accommodation near O'Hare International Airport (ORD)?
Hilton Chicago O'Hare Airport is a popular 4-star hotel featuring 2 restaurants and 2 bars. It's located a short 0.1 mi (0.1 km) from O'Hare Intl. Airport. Other good options close to the airport are Edward Hotel Chicago and Best Western At O'Hare.
What is staying in Winnetka like?
Visitors can enjoy all that Winnetka has to offer including the shopping, forests, and sporting events. Tourists can also enjoy the city's restaurants and coffeehouses. Top sights around the area include Wrigley Field, Naval Base Great Lakes, and Michigan Avenue. In Winnetka, there are 2 hotels and other accommodations to choose from. Find out more about Winnetka.
What should I do while I'm visiting Winnetka?
Favorite places to visit include Lake Michigan, Chocolate Box, and Maple Street Beach. Additionally, you'll find Wrigley Field and Naval Base Great Lakes in the area. Check out what more to see and do in Expedia's Winnetka guide.
What's the best way to get around Winnetka?
To see more of the surrounding area, hop aboard a train at Winnetka Station or Winnetka Indian Hill Station. If you want to venture out around the area, you may want a rental car in Winnetka for your journey.
What's the seasonal weather like 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.

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