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Spending the Weekend in Chicago

Planning a trip to the Windy City for a weekend jaunt? Here’s what to know…

Chicago

Chicago

Chicago, while it typically pales in comparison to New York City or Los Angeles, is a fascinating, cosmopolitan and exciting city to visit. The architecture if phenomenal, with three of the world’s tallest structures including the AON Center, the Sears Tower, and John Hancock. It also has attractions such as the Shedd Aquarium.

If you really want to get an authentic feel for Chicago, summer is a great time to visit. The winters can be pretty harsh in this Midwestern Metropolis, which isn’t necessarily conducive to sight-seeing. Another reason Chicago is great in the summer is because of the access to Lake Michigan. You can see Chicago at its finest during the summer months when residents and visitors gather on the beach shores of the lake, go boating and just enjoy an active waterside lifestyle.

The Highlights

One of the most notable and convenient features of Chicago is the L train. You can take it from O’Hare airport and get right to downtown inexpensively and quickly. You can also access many Chicago hotels from the looping train.

If you love architecture, consider taking the Chicago Architecture Foundation’s tour, aboard the First Lady. It’s a ninety-minute tour along the Chicago River, and you’ll get in-depth views and information about over 50 iconic Chicago buildings, as well as some lesser known ones.

If you’re a shopping visit the Magnificent Mile, which is an enormous row of shopping, from high-end designers to smaller and local boutiques. Here’s where you’ll find the original Marshall Field’s store, which opened in the mid-1800s.

The Art Institute of Chicago is a fabulous cultural option if you love art. You’ll find pieces from the likes of Salvador Dali, and there’s an onsite café that is great for grabbing a quick bite.

As far as entertainment, you may consider a visit to The Second City. This comedy company is an icon, having launched the careers of people like Tina Fey and Stephen Colbert.

Another apparent Chicago venue worth visiting is Wrigley Field. You can get a Chicago-style hot dog while you’re there.

Finally, you can’t miss the Willis Tower Skydeck, which allows you to test your tolerance for heights while taking in fabulous city views. It once held the distinction of being the tallest building in the world, and now it’s ranked as the second tallest in the U.S.

If you have time to pack in just a few more things during your weekend, make it all about the food and the music. Chicago is known for amazing jazz and live music venues, including the House of Blues as well as smaller and lesser known options. There are also two locations of Blues Chicago, a well-known club that features only local Chicago performers. Grab a deep dish signature Chicago-style slice of pizza and you’ll round out your weekend in the Windy City.