A Weekend in the Windy City: Where to Go and What to Eat

Vacation in Chicago


Chicago is a city filled with great museums, restaurants, theater, and shopping.  To make the most of your weekend in Chicago, put these attractions and experiences on your agenda.

Take a Picture with The Bean

Millennium Park Campus is home to Chicago’s famous artwork, Cloud Gate, more commonly known as The Bean.  While you are there, check out the Crown Fountain, a pool with two 50-foot towers where faces of Chicago residents spout water.  In the winter, you can ice skate on the plaza.    All of the park’s sights are free, except for the Art Institute of Chicago and the Harris Theater.

Did Someone Say Free?

Speaking of free, Chicago’s museums offer certain free days throughout the week.  The Chicago Children’s Museum is free on the first Sunday of every month for visitors 15 and under or Thursday nights from 5-8pm.  The Oriental Institute, National Museum of Mexican Art, Money Museum, and Lincoln Park Zoo are also free every day. 

Check out Navy Pier

Occupying 50 acres of prime Chicago waterfront real estate, put Navy Pier on your must-see list.  It offers free music, restaurants, indoor gardens and houses the largest rooftop bar in Chicago.  Take a ride on the Centennial Wheel, which was inspired by the first Ferris wheel ever that debuted at the Chicago World Fair. 

Stroll Down the Riverwalk

There is so much to see and do at the Riverwalk.  You can kayak between the skyscrapers or take an architectural boat tour.  Or, fish off the pier and do some birdwatching.  The Riverwalk is also a great place to take a break from sightseeing and have a drink.    Our High Low Cardigan can take you from day to night on the Riverwalk. 

Not for the Faint of Heart

The city has two observation decks that are in two of the tallest skyscrapers.  One is at the Skydeck at Willis Tower, the tallest building in the Western Hemisphere, where you can step out on The Ledge (1,300 feet above ground).  The other is Tilt at 360 Chicago, which tips you out and over The Magnificent Mile and gives you an amazing view of the city.   The fastest elevators in the country will take you up to the 94th floor in only 40 seconds, so be ready!

Eat Up

You cannot go to Chicago without trying their infamous deep dish pizza, with a thick and crumbly crust and a chunky layer of tomato sauce.  Giordano’s or Lou Malnati’s have the real deal.  You also have to try Chicago-style hot dogs, which have seven toppings, but ketchup is not one of them.  If you are planning a winter trip, Chicago Restaurant Week will be held from January 24-February 9, 2020.  Yum! 

Spend Your Time Shopping

 When planning out the city, the architects envisioned a grand boulevard, similar to the Champs Elysee in Paris that connected the south part of Michigan Avenue with the north bank.  While Chicago’s Magnificent Mile is the place to shop in the city, it is also where you can find architecture by Frank Lloyd Wright, Louis Sullivan, and Miles van der Rohe.  Stop into one of the great restaurants when you are done getting your shopping on.  If you are there in November, check out the Lights Festival, which kicks off the holiday season. 

Catch a Game

No matter what time of year you visit Chicago, there is guaranteed to be some sporting event to watch.  Home of the Bears, Blackhawks, Bulls, Cubs, and White Sox, Chicago is the center of major league sports. 

A weekend isn’t long enough to get to all that Chicago has to offer, which means you’ll just have to go back again!  Check out our website for more great sweaters to pack for your trip.

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