Winnetka Holidays from AU$963

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Your Winnetka Holiday

When a city stay is calling, answer it with a holiday package to Winnetka. With all your travel needs in place before you leave, all you have to do here is focus on having the time of your life. Northwestern University, Chicago Botanic Garden and The Glen Club are just some of the many sights worth exploring during your trip to Winnetka. Expedia can help you escape your daily routine. Tailor your holiday to Winnetka to suit your style of travel, whatever that may be!

The Latest Winnetka Holiday Deals

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$1,181, price is now AU$963 per person
AU$963
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!

Reviewed on 7 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,361, price is now AU$1,027 per person
AU$1,027
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on 11 Oct 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was AU$1,295, price is now AU$977 per person
AU$977
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on 4 Oct 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,263, price is now AU$971 per person
AU$971
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was AU$1,290, price is now AU$1,062 per person
AU$1,062
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Fabulous suite overlooking Millenium Park and Lake Michigan. Clean, attentive staff, and good amenities. Walk to everything.

Reviewed on 10 Oct 2025

Winnetka Holiday

Winnetka Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
12,500
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Rosemont Theatre, Riviera Theatre and Parkway Bank Park Entertainment District

Our pick of the best Winnetka Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,333 reviews)
"Very clean"

Reviewed on 7 Oct 2025

Get rates
Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 12 Nov to 13 Nov
AU$149
12 Nov - 13 Nov
includes taxes & fees
7.8/10 Good! (2,425 reviews)
"Excellent location, clean and good room partners"

Reviewed on 6 Oct 2025

Freehand Chicago
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
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 9 Nov to 10 Nov
AU$276
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"

Reviewed on 7 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,399 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Winnetka

Navy Pier

Navy Pier

4.5/5(64 reviews)

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

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

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

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Winnetka

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Winnetka

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