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Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

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Our top choices for Winnetka hotels

Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (3,033 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is ฿2,902
฿4,031 total
includes taxes & fees
25 May - 26 May
Freehand Chicago
Lobby

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,002 reviews)
"All around great stay. "
United States
Nicholas
The price is ฿4,206
฿5,001 total
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Exterior

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,510 reviews)
"Clean room, excellent staff and concierge, great location."
United States
Terri
The price is ฿3,228
฿4,795 total
includes taxes & fees
25 May - 26 May
Claridge House Chicago, Tapestry Collection by Hilton
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,239 reviews)
"Nice place to stay"
United States
Jimmie
The price is ฿4,532
฿5,388 total
includes taxes & fees
25 May - 26 May
Aloft by Marriott Chicago Mag Mile
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,146 reviews)
"Great place! Would stay again!"
United States
Tasha
The price is ฿3,575
฿4,250 total
includes taxes & fees
26 May - 27 May
Central Loop Hotel
Lobby sitting area

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,303 reviews)
"Excellent location and friendly staff."
United States
Radhika
The price is ฿3,777
฿4,491 total
includes taxes & fees
26 May - 27 May
Club Quarters Hotel Wacker at Michigan, Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (2,606 reviews)
"Staff was friendly and helpful.. location was great"
United States
Amber
The price is ฿3,668
฿4,361 total
includes taxes & fees
25 May - 26 May
Travelodge by Wyndham Downtown Chicago
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,504 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is ฿6,183
฿8,474 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,712 reviews)
"Amazing place"
United States
Rodolfo
The price is ฿2,830
฿4,360 total
includes taxes & fees
25 May - 26 May
Hotel Felix River North/Magnificent Mile
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,785 reviews)
"Very clean room, nice breakfast and really nice hotel restaurant"
United States
Hugo
The price is ฿4,532
฿5,962 total
includes taxes & fees
25 May - 26 May
La Quinta Inn & Suites by Wyndham Chicago Downtown
Restaurant

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very good, (2,696 reviews)
"we've stayed there many times for years & have always been very satisfied ."
United States
cheri
The price is ฿3,786
฿4,501 total
includes taxes & fees
26 May - 27 May
Best Western Grant Park Hotel
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,210 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is ฿5,184
฿7,093 total
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,452 reviews)
"Great stay"
United States
Ontario
The price is ฿3,959
฿4,707 total
includes taxes & fees
25 May - 26 May
The Chicago Hotel Collection - Magnificent Mile
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,128 reviews)
"Nice clean hotel downtown."
United States
Richard
The price is ฿4,355
฿5,177 total
includes taxes & fees
25 May - 26 May
Congress Plaza Hotel
Nightclub

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,506 reviews)
"Definitely In going to this hotel again soon Very nice hotel staff and clean and the location was great "
United States
Mary
The price is ฿4,206
฿5,001 total
includes taxes & fees
26 May - 27 May
Club Quarters Hotel, Central Loop, Chicago
Lobby

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,187 reviews)
"excellent stay"
United States
Jaeyoung
The price is ฿4,129
฿4,909 total
includes taxes & fees
25 May - 26 May
River Hotel
Indoor pool

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,072 reviews)
"Great location ,service and staff "
United States
Tamar
The price is ฿7,629
฿10,212 total
includes taxes & fees
25 May - 26 May
InterContinental Chicago Magnificent Mile by IHG
Exterior

Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,931 reviews)
"Was a great stay- all you need and great location!"
United States
Sharon
The price is ฿4,567
฿5,429 total
includes taxes & fees
25 May - 26 May
Hilton Garden Inn Chicago Downtown Riverwalk
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,845 reviews)
"Best hotel breakfast around...for free! Excellent buffet, and cook to order omelets are restaurant quality"
United States
Michael
The price is ฿5,283
฿7,236 total
includes taxes & fees
25 May - 26 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,335 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is ฿5,712
฿7,939 total
includes taxes & fees
25 May - 26 May
Swissotel - Chicago
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.
See properties

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 theatre.

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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"."
Jeff 3-night trip
Posted 1 hour ago
Hilton Chicago/Magnificent Mile Suites

More cheap stays in Winnetka

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

22 West Algonquin Road Arlington Heights IL
The price is ฿1,878 per night from 5 Jun to 6 Jun
฿1,878
฿2,103 total
5 Jun - 6 Jun
includes taxes & fees
5.4/10 (1,002 reviews)

Frequently asked questions

What's the best place to stay in Winnetka?
Located 17.1 mi (27.5 km) from the heart of Winnetka, Congress Plaza Hotel is a top choice for your stay, based on our traveller data. Other good choices for your trip to the area are Hotel Riu Plaza Chicago and The Chicago Hotel Collection - Magnificent Mile. See all available top hotels, or vacation rentals in Winnetka.
If I need to cancel my hotel reservation in Winnetka, will I receive a refund?
Yes! The majority of hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winnetka.
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 coffee shops. Top sights around the area include Wrigley Field, Naval Base Great Lakes and Navy Pier. In Winnetka, there are 2 hotels and other accommodation options to choose from. Find out more about Winnetka.
What should I see while I'm in Winnetka?
Favourite 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. Take a look at what more there is to see and do in Expedia's Winnetka guide.
How can I get around Winnetka?
To venture out into 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 in Winnetka?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Winnetka is 1216 mm.

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