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Chicago: Your Kind of Town. Five fun “insider” things to do in the Windy City

My wife Cindy and I run our own consulting business, and over the past 20 years, we’ve been lucky enough to have traveled the world over, for business and pleasure. But as much as we love traveling, the best part is coming home to Chicago.

Steve Crescenzo

The lakefront, beaches, architecture, restaurants, theater, museums ... Chicago has it all. And now that Finnair is offering direct flights to Chicago, it’s a great time to visit. 

Every guidebook will tell you about the museums, Millennium Park, Wrigley Field, Navy Pier, and other popular attractions. And you should see all of them! But here’s an insider’s Guide to five Chicago experiences you won’t want to miss. 

1. Take a walk on the north side

If you are staying downtown, ask your concierge or any bellman the quickest way to the lakefront (it will most likely be walkable, from your hotel). Then the fun starts. From downtown, head north along the lake front path, which runs the entire length of the city. Watch out for bikers, roller bladers, and runners! It’s a popular route, with Lincoln Park to the left, Lake Michigan to the right, and the skyline at your back! 

First, you’ll hit Oak Street Beach, where you’ll want to grab some bench and people watch. Then keep heading north until you get to the North Avenue Bridge. You can’t miss it ... it is the only bridge spanning Chicago’s famous Lake Shore Drive. 

Head over the bridge and you’ll be in the heart of Lincoln Park. If you are there in season, the city’s best Farmer’s Market is right there. And if you head two more blocks north, you’ll hit Lincoln Park Zoo—one of the great free Zoos in the world.

Grab lunch or a cocktail at Café Brauer, which is right in the heart of the Zoo. If you’re up for it, you can head west a couple of blocks to Clark Street, and then take Clark all the way back downtown, heading straight through the historic Lincoln Park and Old Town neighborhoods. 

2. Rolling on the River

Chicago’s River Walk is a must. Start at the Michigan Avenue end, and stroll the river. There are several cafes you can pop into, or better yet grab a drink and a seat outside and watch the boats and kayaks and party boats float by. 

While you are on the River, sign up for Chicago’s famous architectural cruise. You’ll get the inside story of dozens of Chicago’s famous buildings. And if you are still there in the evening, walk the River to Wells Street for “Art on the Mart”, which is “The largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of the Merchandise Mart.” Pretty amazing ... and free!

3. Pizza two ways

Chicago is known for its deep dish pizza ... but here’s a little secret. Chicagoans are thin crust people! Most of us only do deep dish if someone is in from out of town and wants to try it. In my opinion, the best deep dish is Lou Malnati’s. Lots of locations in the city, but the best is the one right by the John Hancock building. 

When we have guests in town, we always start with a ride up to the restaurant on the 95th floor of the Hancock for a cocktail. The views are unreal. Then, we head to “Lou’s” as Chicagoans call it, for a pie. If you’re an Italian sausage fan, you’ll fall in love with Lou. 

And if you’re looking for thin crust, Chicago has the best. And the best of the best is Vito and Nick’s. You’d need a car to get there, as it’s on the South Side ... but it has been a neighborhood favorite since 1920! No car? No worries. The city itself has dozens of thin-crust places. Just ask your concierge for the nearest one. (Insider’s Tip: Ask for the best “tavern-style” pizza. That’s what Chicagoans call thin crust). 

4. A case of the Blues

Chicago has some of the best live music venues in the country ... but we are known for the Blues. And the best place to catch a set is The Kingston Mines, on the north side of the city. They have two separate stages ... so when one band takes a break, the other band starts up on the other stage ... so it’s non-stop music! It’s probably a $10 cab or Uber from downtown, and worth every penny. And if you’re more into Jazz than Blues, Andy’s Jazz is right downtown and has been a Chicago institution since 1951. 

5. Oysters in Chicago? Yes, please!

Chicago has hundreds of good restaurants, but it isn’t exactly known for its seafood. But if you have a taste for oysters, head to Quality Crab and Oyster Bar on Halsted (not that far from the Kingston Mines if you want a great night out). 

They fly in fresh oysters every day, and charge about half of what the fancy downtown restaurants charge. Ask for a seat at the bar. If you’re lucky, Rudy will be taking care of you. And he’ll give you even more insider tips on Chicago! (Oh, they also have the best fried chicken in town, and a great Chicago Burger!). 

Bonus Tip 

If you are here in the winter (I know you Finns aren’t afraid of a little cold weather), you must skate “the ribbon” in Maggie Daley park. It’s open from the end of November until March, and you can rent skates there. 

Whatever you end up doing in Chicago, you’ll have a great time. We are a friendly bunch!


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