Vacation Rentals in Winnetka

Sentral Michigan Avenue

808 SOUTH MICHIGAN AVENUE, Chicago, IL

Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...

Kasa Magnificent Mile Chicago

One Superior Place, Chicago, IL

Stay at this 4-star aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular ...

Level Chicago – Old Town

1140 North Wells Street, Chicago, IL

Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our ...

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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.

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Popular places to visit

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.

Magnificent Mile - River North showing night scenes, a city and signage

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.

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 theater scene.

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.

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 entertainment choices in this vibrant area.