A Weekend in the Windy City

Chicago, the Windy City, has so much to offer locals and tourists alike, from the best world-class museums to the most fun leisure and entertainment destinations. A weekend here will allow you to relax, shop, eat and play in an iconic city full of important history and culture. This is the perfect place to take a weekend getaway, and here are just a handful of places where you can spend your weekend!

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Navy Pier Chicago Dollarphotoclub

Navy Pier

The Navy Pier is the number one leisure destination in the Midwest and remains one of the most important historic landmarks in Chicago. The Pier attracts over nine million visitors annually, providing a highly popular and convenient public meeting spot and allowing guests to enjoy the natural beauty of the lakefront while marveling at the iconic urban skyline of the city. While here you can let your inner kid run rampant at the Navy Pier Park (don’t miss a chance to ride the Ferris Wheel), eat some of the freshest seafood at Bubba Gump Shrimp Co., or admire the horticultural wonders of an indoor botanical garden at Crystal Gardens.

Museum Campus - Museum Campus is actually a 57-acre museum park that sits near the banks of Lake Michigan and surrounds three of the city’s most notable world-class museums. This campus is a convenient location to visit many different places quickly or separate your group in close proximity if you can’t decide. You will have the chance to visit the Field Museum of Natural History, Adler Planetarium, or Shedd Aquarium, all highly popular museums dedicated to different areas of natural science.

Willis/Skydeck OR 360 Chicago 

An essential part of any visit to Chicago involves seeing that gorgeous and iconic skyline from above, something you will get the chance to do either at the Willis Tower (Skydeck) or 360 Chicago (previously the John Hancock Observatory). Willis is the tallest building in the Western Hemisphere and will allow you to stand on The Ledge, a glass enclosure four feet away from the building that allows you to look down upon the city from 1,353 feet in the air. 360 Chicago allows you to see the same amazing views from a different vantage point, 1,000 feet in the air. 360 also holds an immersive experience called Tilt, facing the guest at a downward angle of 30 degrees to see the Magnificent Mile below from a completely different angle.


Millennium Park - Millennium Park is Chicago’s premier green space, a lively and vibrant gathering spot that serves as the backdrop for hundreds of free cultural events. This park holds a state-of-the-art collection of architecture, art, and landscape design and offers daily programs, concerts, and tours within its boundaries. Inside you will see the Jay Pritzker Pavilion, the famous outdoor bandshell where you can catch concerts, the Cloud Gate, the famous bean that provides a mirror-like surface to see the city skyline in, and Lurie Gardens, an urban garden with impressive perennials, footbridges, and shallow pools that will make you forget you are in the city!

Magnificent Mile

Every weekend away seems to involve excessive or well-deserved retail therapy, and a weekend in Chicago is definitely not lacking in options for just that. The Magnificent Mile is a 13 block, a full-mile stretch of some of the best shopping, dining, and landmarks in the entire city. It is known as one of the greatest avenues in the world and ranks in the top ten in hospitality and retail in the nation. Here you can explore the brand name world of Chanel, Burberry, Coach, and department stores such as H&M and Macy's. There are eateries to please every palate, offering dining options from gourmet and authentically ethnic to casual and fast food fares.

Tommy Guns/Blue Man Group - No trip to the big city would be complete without proper entertainment, and Chicago has you covered there too, offering several nightly entertainment options. Some of the most unique and fun shows include the Blue Man Group, a heart-pounding performance that combines music, technology, and comedy to create a form of entertainment that defies categorization. For a little less thrill but still all the bang for your buck you can get head over to Tommy Gun’s Garage, a unique and exciting history lesson that doubles as the most exciting and interactive comedy show in the city. This one will pull you on the stage and allow you to do the Charleston with the flappers and gangsters of the roaring twenties!