Chicago Vacation Rentals

Areas near Chicago

• Illinois (113)

Explore Chicago Vacation Rentals

One of the largest, busiest, and most cosmopolitan cities in the United States, Chicago, Illinois, is an exciting place to visit. If you're planning a trip, summer in Chicago is ideal. With warm and balmy weather, crowds gather on the lakefront beaches during the day, turning out for dancing and revelry at night. Like all of IL, winters are cold and blustery in Chicago but the chilly months shouldn't be considered off-limits to travelers. During the winter, there are plenty of cultural activities to keep you busy and the Christmas lights along Michigan Avenue are a beautiful sight to behold as you do your holiday shopping.

A sophisticated city, there is an ever-increasing number of gourmet restaurants in Chicago's varied neighborhoods, as well as a fabulous nightlife. Live music is common, with something to suit every taste, from jazz to folk to hard rock. Among the many music and art festivals in town, the renowned Chicago Blues Festival is held every June in Grant Park. Chicago also maintains some of the best live theater venues in the United States. Be sure to visit the renowned Steppenwolf Theater in Lincoln Park if you wish to see famous names live on stage.

For kids, Chicago offers more than its famous deep-dish pizza. There are family-friendly attractions throughout the city, from Adler Planetarium to Shedd Aquarium. In the summer, the beach is a great place to enjoy the gentle surf and fresh water of Lake Michigan. The Navy Pier is another ideal family destination, offering shopping, entertainment, and great views of Chicago's beautiful skyline.

When in Chicago, don't miss:

-Magnificent Mile: Lined with fashionable boutiques and huge department stores, this busy stretch of Michigan Avenue is the best place for shopping in Chicago.

-Art Institute of Chicago: This is a wonderful fine art museum with a top-notch exhibit of Impressionist art and American art.

-Millennium Park: The northwest region of Grant Park is home to Frank Gehry's Pritzer Pavilion, as well as some lovely public sculptures.

-Lincoln Park Zoo: This excellent wildlife park is free to visitors and exhibits exotic animals from all over the world.

-Sears Tower: Ascend the elevators to the famous Sears Tower Skydeck, a panoramic observatory located on the 103rd floor of the building.

-Oak Street Beach: Chicago's famous stretch of sand is located on the north side of the city.

A vacation rental gives you the opportunity to stay in any of Chicago's charming residential neighborhoods. In the summer, an apartment rental with lake views and a short walk from the shore is an ideal choice. A trendy condo is best for those who'd like to stay close to the action downtown, while a small cabin in North Chicago can be a more peaceful choice during the winter months. See more...

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Additional Resources

• Lollapalooza
• Summerfest
• Chicago Marathon