Visiting Chicago: Our Nine Favorite Things to Do in the Windy City

If you’re in Chicago for HIMSS, you might be thinking of it as just another business trip. In fact, you’re probably thinking you’re going to be too tired to even do anything in Chicago by the time you’re done with the day at McCormick (don’t be ashamed, it happens). Through our many experiences in Chicago, we’ve decided to put together a list of HIMSS-friendly Chicago sights and eateries.

1. The Magnificent Mile

The Magnificent Mile is probably one of the easiest things to see while in Chicago. It is a series of mid-range and high-end shops, restaurants, museums and hotels. It is the stretch of Michigan Avenue from the Chicago River to Oak Street.

2. The Willis Tower. Skydeck – $19.50

Image by flickr user baggis

The Willis Tower, formerly the Sears Tower, was once the tallest building in the world–for 25 years. Today, it is the second tallest buildling in the United States and the twelfth tallest in the world. Visitors can take an elevator ride to the Skydeck on the 103rd floor of the building. If you’re adventurous, or unafraid of heights, be sure to step out into one of the glass ledges. These glass boxes sit 1,353 feet above the city streets, and on a clear day, you can see across Lake Michigan to Indiana, Michigan, and Wisconsin.

3. 360 Chicago (formerly the John Hancock Observatory). $19

Image by flickr user dan_h

The Hancock Observatory was the building that was intended to be the tallest in the world, but the one that never quite made it. It is currently the fourth tallest building in Chicago, 33rd in the world. It has an interesting history, as construction was halted in 1967 due to a flaw found with the method used to pour concrete. This forced the owner into bankruptcy, and the John Hancock Mutual Life Insurance Company purchased the building to resume construction.

Today, you can visit an observatory deck in the building, where you can famously get a 360 degree view of the city. Another selling point is their combo pass, “Sun and Stars.” You can pay $26 for two visits within 48 hours, to see the sights during both night and day.

4. Cloud Gate (“The Bean”) Millennium Park

Image by flickr user tommychheng

Cloud Gate, affectionately known as ‘the bean,’ is the name of a polished-steel sculpture by British artist Anish Kapoor. It is the artist’s first public work to be installed in the United States. The sculpture resides in Chicago’s Millennium Park, on the AT&T Plaza. It’s called Cloud Gate because you can see the entire Chicago skyline in it (including the clouds. Who knew?).

The Cloud Gate is unequivocally “Chicago.” In other words, see it at least once, or you haven’t really been to the city.

5. Smith & Wollensky 

Image by flickr user cmozz

If you need to get that perfect, classic steak meal, go nowhere else. (You can also celebrity-watch.) The lakefront location in Chicago is one of only nine in the states. The company itself says, ‘We offer a timeless, vibrant, yet relaxed atmosphere that envelops guests in gracious hospitality. It’s a dining experience that offers simple refinement in the grand tradition—conveying unequivocally “YOU’VE ARRIVED™.”’

6. The Grand Lux Cafe

Image by flickr user phatpat

The Grand Lux Cafe was created by the same people responsible for The Cheesecake Factory. The first one ever opened at the Venetian in Las Vegas, and today, there are 11 locations in the United States. The menu is inspired by European cuisine and the decor is intended to come across clean and modern, yet warm and inviting (their words, not ours. Click here for the website.)

Be sure to try the beignets (with raspberry, vanilla, and chocolate sauce), one of our absolute favorites. There was much joy and hunger had in the office when we discovered this great picture.

Image by flickr user corsinet

7. Navy Pier

Image by flickr user cjsmithphotography

The Navy Pier has been around since the early 1900s, and has evolved in its uses. It has almost always, however, been used for recreation. It offers sightseeing tours through companies like Seadog Ventures (20% off coupon from the city of Chicago here). Dinner cruises are also popular, on ships like the Spirit of Chicago. There are also museums and classic theme park attractions, like rides etc. Go here for more information about the many, many things to do on Navy Pier:

8. Wrigley Field & the Chicago Cubs

Image by flickr user compujeramey

First of all–even if you don’t want to go see the Cubs, Wrigley Field is a great place to visit. It was built in 1914 and has been home to the Cubs for 99 years. For $25, you can take a tour of the ballpark.

Now, if you do want to see the Cubs, you’re in luck. They play the Reds (at home, obviously) April 13, 14, and 15, all at 7:05 pm. You can get your tickets here priced anywhere from $9 for the least expensive to $119 if you want to drop some cash for a dugout box seat.

9. Deep dish pizza at Giordano’s ~$20/pizza

Image by flickr user jameshawk

We’re on an eternal quest to find the best deep dish pizza in Chicago, and since we don’t live there, we have to subsist on going once every once in a while (RSNA and HIMSS, usually). Last time, we went to Giordano’s, and it certainly lived up to the fame.

Image by flickr user 40726522@N02

The pizza was cheesy, warm, thick, and delicious. The bruschetta was also excellent. (One of us also got the Greek salad, and if you’re a fan of feta and olives, it’s an amazing route to take.).

We’re always open to suggestions–so tell us in the comments if we need to visit another delicious pizza place.

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