Winnetka

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.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is P8,165 per night from May 26 to May 27
P8,165
P9,707 total
May 26 - May 27
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! (10,218 reviews)
Great location for a good price. Staff was helpful and the place was nice. It’s a little older building and shows a bit of wear here and there but not a bad spot at all. Overall worth the price!e

Reviewed on May 12, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is P9,108 per night from May 25 to May 26
P9,108
P12,570 total
May 25 - May 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,119 reviews)
El desayuno estuvo bien

Reviewed on May 12, 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is P9,137 per night from May 25 to May 26
P9,137
P10,863 total
May 25 - May 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,300 reviews)
Beautiful Hotel great location

Reviewed on May 12, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,558 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! (1,159 reviews)
It’s a Travel family trip

Reviewed on May 10, 2026

Sentral Michigan Avenue
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 ...
9.4/10 Exceptional! (752 reviews)
Ideal location in downtown. Clean well equipped nice views

Reviewed on May 11, 2026

Kasa Magnificent Mile Chicago
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! (474 reviews)
Check in requires an online form including a background check at your expense. It’s a nice place. Unbelievable 8th floor of recreation, spa w sauna and steam room w showers, tv, pool, ping pong, tvs everywhere, the backyard includes half court ncaa size backboard bball, bags, dog park, multiple outdoor ...

Reviewed on May 6, 2026

Level Chicago – Old Town
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

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Soldier Field

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Millennium Park

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

P1,624
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

P2,646
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

P2,405
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

P2,303
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

P2,436
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

P1,477
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Winnetka