Winnetka, IL

Travel Guide

A suburban street with a stone house, a tree, and a clear sky.
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$187 nightly
The price is $222 total per night from Sep 27 to Sep 28
$222 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundable
$179 nightly
The price is $212 total per night from Oct 7 to Oct 8
$212 total
Oct 7 - Oct 8
Total with taxes and 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! (10,168 reviews)
"F"

Reviewed on Sep 19, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$160 nightly
The price is $191 total per night from Sep 29 to Sep 30
$191 total
Sep 29 - Sep 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,266 reviews)
"Vintage gorgeous property. The lounge was awesome. The breakfast was gourmet. The rooftop view was great. The room was incredibly spacious and clean! Too notch!"

Reviewed on Sep 19, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,413 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 ...
9/10 Wonderful! (1,326 reviews)
"The place was expensive, but so are all of the hotels in this part of Chicago."

Reviewed on Sep 19, 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! (910 reviews)
"Very happy with the stay. WiFi went off a couple of times, but was addressed promptly"

Reviewed on Sep 17, 2026

Kasa Magnificent Mile Chicago
Kasa Lake Shore Chicago

Kasa Lake Shore Chicago

4 out of 5
446 East Ontario Street Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Popular attractions Michigan Avenue and Chicago Riverwalk are ...
Kasa Lake Shore 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.

Stay near popular Winnetka attractions

Home Alone House

Enjoy an outing to Home Alone House during your stay in Winnetka. Amble around the area's forest or visit its shops.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

$28
per adult
96% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
LEGOLAND® Discovery Center Chicago

LEGOLAND® Discovery Center Chicago

$26
per adult
92% of travellers recommend
LEGOLAND® Discovery Center Chicago
See all activities in Winnetka

Frequently asked questions

Is Winnetka worth visiting?
Winnetka is worth visiting for its diverse food scene, where travelers can enjoy a range of Latin American and European cuisine. The destination also offers practical transit access, making it easy to explore with convenient train services available.
When is the best time to visit Winnetka?
The best time to visit Winnetka is from May through September, when the weather is generally pleasant for travelers. For fewer crowds and better value, the quieter months of December through March are a good option. During this period, you can expect cooler temperatures and potentially more attractive rates.
What is Winnetka known for?
Winnetka is known for being home to the iconic Home Alone House and the unique Chocolate Box. Travelers can also enjoy Elder Lane Beach, and explore a vibrant Latin American food culture within this city.
What is a good itinerary length for Winnetka?
A good itinerary length for Winnetka is one to two days to see key attractions like the Home Alone House, Chocolate Box, and Elder Lane Beach. An extended stay of three to four days allows you to take a Chicago Movie Locations Tour or a Private Chicago Suburbs Movie Sites Tour, and enjoy local dining options.
How do you get around Winnetka?
Winnetka travelers can easily get around using the local train service. You'll find convenient access at stations such as Winnetka Indian Hill Station and Winnetka Station, connecting you to various points. For broader exploration or specific destinations, rideshare services are also available throughout the area.
What are the top things to do in and around Winnetka?
Winnetka offers unique landmarks, a beautiful beach, and fun tours exploring local movie history:

  • Visit the Home Alone House, a famous landmark.
  • See the Chocolate Box, another notable landmark in the area.
  • Relax at Elder Lane Beach, a scenic spot by the water.
  • Take a Private Chicago Suburbs Movie Sites Tour to explore film locations.

How do I plan a trip to Winnetka?
To plan your trip to Winnetka, search for places to stay and book flights in advance. Explore attractions like the Home Alone House and Elder Lane Beach, and consider a Chicago Movie Locations Tour. You can use train services, or book a rental car for more flexibility. Always have indoor backup plans for outdoor activities.
What cuisines can you find in Winnetka?
In Winnetka you can find French cuisine, with dishes like croissants, coq au vin, and steak frites. Travelers also have options for Latin American (Mexican), Mediterranean, Italian, Asian, and North American fare, plus speakeasy and wine bars, and coffee and dessert shops.
Can I book a refundable hotel in Winnetka?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Winnetka by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Winnetka with Expedia?
Expedia makes it easier to plan your Winnetka trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Winnetka?
The best choice depends on your travel style. Hotels in Winnetka can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Winnetka trip on Expedia?
Once you've booked your Winnetka trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Winnetka trip?
Expedia offers customer support before, during, and after your Winnetka trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Winnetka?
If it's your first trip to Winnetka, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Winnetka hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Winnetka hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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