Things to do in Chicago

Frank Sinatra made a good point about Chicago.

It is a very fun town and it’s my kind of town. I’ve been there many times in just about every season and June is the best time to go. It’s like a mini New York, but with a slower pace and friendlier people.

The temperatures are just right in June… humidity isn’t (yet) too much, the cool cars are all usually on the road and if you can visit before school gets out, you can really enjoy this great city without an overload vacationing families.

This last trip, we stayed downtown, in the financial district at the City Center W Hotel. Good choice. This was a great location and was easy for me to get around during the day.

The downtown core is actually very easy to navigate, especially by cab! If you’re a walker, you can actually cover most of it on foot, which is great because there’s lots to see.

It is true what they say about this city, it IS windy. But in the summer months, this is a welcome characteristic.

Here are the top five things I think anyone should consider doing while in Chicago:

  1. Visit Navy Pier at night and ride the ferris wheel, then watch the fireworks. Romantic and fun!
  2. Go up to observation deck of either the Sears Tower or the Hancock Building. The Hancock Building is more central. Both views are impressive, especially during that moment when dusk falls and twilight starts.
  3. If you’re into architecture (which I am), Chicago has the best collection of modern influence mixed with the classics of ANY major American city – so take a narrated, guided boat tour on the Chicago River through the city. It takes a few hours and is worth it just to hear about some of Chicago’s amazing history while enjoy an urban view that is second to none.
  4. Eat! Chicago is a great town for chowin’ down. If you like Mexican, Rick Bayless, runs amazing Mexican restaurants called Topolobambo and the Frontera Grill (the latter is an al fresco power lunch spot with some incredible menu options), both within walking distance of downtown. And of course, there’s places like Gino’s East, for authentic deep dish Chicago pizza (if you’re into an inch of cheese onto of your pie!). My wife tells me it was great pizza, since I can’t eat it.
  5. Walk the Magnificent Mile. This is a stretch along North Michigan Avenue to Oak Street Beach with all the great shops and restaurants you can think of. One of my favorites is RL – Ralph Lauren’s restaurant at North Michigan and East Chicago Avenue – about halfway down the Magnificent Mile walk. They have the absolute BEST margaritas there and the people watching is a gas. We met some fantastic, friendly folks at that restaurant. Walking the Magnificent Mile is something that you should plan to do for most of the day.

All of of these things would make for the basis of a great weekend in Chicago. Other notable, but not “top five” things to do would be seeing a show, visiting the Chicago Museum of Contemporary Art and catching some outdoor music in the beautiful Grant Park.

Getting to Chicago is easy from any North American city – Chicago O’Hare is a hub airport for much of the United States and is one of the busiest airports in the world.

Take a cab into town from the airport if you’re not going to leaving downtown Chicago – you can get by with out a rental car if you’re there on a conference or don’t want the hassle and don’t need to stray too far. Cabs are a little on the expensive side, but well worth the convenience.


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I value good design, growth, effectiveness, simplicity, profitability, lots of sleep, tons of laughter and above all, freedom. If it makes money - it's a business. If it doesn't make money - it's a hobby. Period.