Sometimes you need a break. You need to get away for a bit, from work, from routine, from the crazy people down the street who are jumping up and down on your last nerve. When I’m feeling this way my first thought is usually to run to the jet and get to some remote island with nothing but surf, sand, and a team of forty people waiting to make my every wish come true. But sometimes you want it all and only have the weekend to do it.
Enter the city break.
Recently I needed a break and had the opportunity to go to Chicago. Chicago is one of my favorite cities in the United States. There are tons of options to entertain you. Last weekend I had 48hrs in that toddlin’ town and was quickly reminded of why the city is so amazing: the people and the food. The people are genuine, friendly, and all around good people. OK so maybe not every single one of them is perfect…Rod Blagojevich comes to mind. But for the most part I’ve only ever met great people in Chicago. The food scene has become one of the coolest in the US. The other great aspect of Chicago is that ever since that little fire in ’71 it is constantly morphing in a way that no other city can.
Here are my six tips on how to make the most out of your weekend visit to Chicago.
Advance planning– I’m a firm believer that anything is possible with enough planning. If we can send people into outer space we can certainly make your city break full of fun. But first you need to do two things:
- Purpose:Figure out the purpose of the trip. Relax? Party? Sightseeing? Catch up with friends? The answer to this will set the tone of your trip.
- List:Generate a list of all the things you want to see and do during the visit.
Gathering of friends– Chicago is a great city to meet up with a group of friends. If you have friends who live there consider getting them all together for a small cocktail party so you can see all your friends at once. And if you don’t have friends in the Chicago area, consider getting a group to come with you. If that doesn’t work, relax – you’ll most likely have some new friends by the end of your 48hrs – it’s one of the friendliest cities around.
Food– Chicago is home to some amazing restaurants. In fact, 23 restaurants have one or more Michelin stars. So gastronomy should always be a big part of your experience. Recently one of my favorite clients was in Chicago so I arranged a private cooking lesson in a two-star Michelin restaurant.
Private guide– I’m not talking about the kind of tour where you have to wait for the 50 other people to get on the bus. Get a private guide who is not only an expert but also someone who is as passionate about a subject as you. From art or architecture to stars and zebra sharks, there is a specialist out there who is interested in sharing their knowledge with you. Sometimes I like to pick something I know very little about and find someone who is a specialist to help enlighten me.
Rest– Regardless of what your goal is for the weekend make sure you take some time to relax. From sleeping in late to treating yourself to the spa treatment of your dreams, make sure you take time to relax and enjoy the experience. After all even rock stars need to regroup every now and then.
The next time you are feeling worn out and tired of doing the same old thing, remember: you deserve a break today. So take it! Who knows? You may come home inspired and full of the most amazing stories and even some new friends.
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