Book Exclusive Winnetka Vacation Packages
Winnetka flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
21c Museum Hotel Chicago
Downtown Chicago
per person
Jun. 20 - Jun. 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Jun. 22 - Jun. 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Silversmith Hotel Chicago Downtown
Downtown Chicago
Save 100% on your flight
per person
Jul. 15 - Jul. 20
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
Level Chicago Fulton Market
Downtown Chicago
per person
Jul. 3 - Jul. 6
just found
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Top Winnetka hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $208 total
May 12 - May 13
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
Free WiFi
Restaurant
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $235 per night
CA $235
CA $276 total
May 21 - May 22
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 staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $242 per night
CA $242
CA $284 total
May 26 - May 27
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Breakfast included
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $219 per night
CA $219
CA $298 total
May 26 - May 27
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Spa
Pet-friendly
River Hotel
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
CA $194 total
May 27 - May 28
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2, Chicago, IL
Free cancellation
The price is CA $245 per night
CA $245
CA $287 total
May 26 - May 27
includes taxes & fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pool
Free WiFi
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
4.5/5(158 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.
Six Flags Great America
4.5/5(5 reviews)
Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.
Michigan Avenue
4.5/5(19 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.
Winnetka Vacations
A memorable, hassle-free adventure begins with getting to know a bit of information about your destination. It's time to discover the basic details about Winnetka!
Around 16 miles (26 kilometers) northwest of central Chicago, Winnetka is one of the neighborhoods that make this city so charming.
Ready to rub shoulders with the locals? 2,700,000 people live in Chicago.
Places to visit in Winnetka
Everyone knows that being around animals can help reduce stress. So, if always being on the move is tiring you out, why not make your way to Wagner Farm? But that's not all there is. Theater can challenge our world views and asks us to aspire to higher things. Catch a play at Writers Theatre and open your mind to some new ideas.Where do you fly into for Winnetka?
Flying into O'Hare International Airport (ORD)? Get through security, step out of the terminal and you'll be 12 miles (19 kilometers) southwest from the heart of Winnetka.Photos of local treasures
Browse Winnetka vacation photos for more inspiration
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