Winnetka, IL

Travel Guide

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.
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.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is AED 496 per night from Feb 14 to Feb 15
AED 496
AED 582 total
14 Feb - 15 Feb
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,832 reviews)
Yes perfectly clean

Reviewed on 24 January 2026

Congress Plaza Hotel
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
The price is AED 389 per night from Feb 5 to Feb 6
AED 389
AED 456 total
5 Feb - 6 Feb
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.4/10 Very Good! (5,616 reviews)
The room was clean. The staff was courteous! The breakfast was ok, the parking is charged extra-absolutely worth it!

Reviewed on 26 January 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is AED 479 per night from Feb 3 to Feb 4
AED 479
AED 670 total
3 Feb - 4 Feb
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,585 reviews)
My stay was truly amazing. Thank you and appreciate the hotel hospitality

Reviewed on 25 January 2026

Hilton Chicago
See all 4,675 properties in Winnetka
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.
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
9.2/10 Wonderful! (1,061 reviews)
Excellent

Reviewed on 23 January 2026

Sentral Michigan Avenue
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street Chicago IL
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our ...
9/10 Wonderful! (416 reviews)
Property was clean, welcoming, pet friendly

Reviewed on 18 January 2026

Level Chicago – Old Town
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (679 reviews)
Everything was very simple. Parking structure connected to building. Building was very good service wise. Safe, quiet, clean. Will be returning

Reviewed on 26 January 2026

Kasa Magnificent Mile Chicago
See all properties in Winnetka
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.

Popular places to visit

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(1,805 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

McCormick Place
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Navy Pier
Soldier Field featuring a skyscraper, modern architecture and a city

Soldier Field

4.5/5(1,256 reviews)

Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Soldier Field
Beautiful autumn colors surround modern architecture in Millennium Park, Chicago during a sunny day

Millennium Park

4.5/5(7,198 reviews)

After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Millennium Park