These days it’s hard to imagine living in America and never having been to New York or LA. And you should go to both these unique and important international cities. Chicago? Nice, but not critical, unless you have some social or business relationship to the city, or a strong interest in American history or art. Chicago used to be considered the cleaner, more all American alternative to New York, but, what with New York having cleaned up and gentrified, I’m not sure that is true anymore.

The winter is very cold, and wind and rainstorms are a year round factor – hence the nickname the windy city. And despite how often it rains, a simple rainstorm can easily result in a 2 hour delay in your flight to or from O’Hare, and it can easily take an hour to get from the airport to downtown. And a single relatively minor act of arson at the airport recently resulted in days of delays and thousands of cancellations. If you bring your own car you can expect to pay $56-58 a night just for parking. So there are some logistical challenges with Chicago, but, as is the case of just about any large city in any developed country, there is plenty to do and see that is worthwhile if you make some effort.

Shopping

You’ve probably heard of Magnificent Mile, which is a stretch of Michigan Avenue running from the Chicago River to Oak Street on the North Side. But it’ just not magnificent; in fact it’s the same old luxury and mid-range stores you’ll see in any major American city and, in fact, just about anywhere around the world these days. If you’re going to walk and get jostled with the crowds, you might as well see the same stores, and a few nicer ones, on 5th Avenue in NYC. But if you’re in Chicago and feel like some shopping, go to Oak street, one block off of Mag mile, which has the usual very big names like Hermes, Tom Ford, and some spillover for Marc Jacobs, as well as a few more unique stores.

Strolling

And if you want to continue your posh stroll, go to the area around Bellevue and Rush, where there are a number of nice white tablecloth restaurants with outside seating and a mini park where you can get gelato and watch the well-heeled, both literally and figuratively, walk by. Just take Wabash instead of Michigan and you’ll by-pass the usual crowds and have a more interesting walk. There’s a Thompson hotel in this area as well.

If you walk along the Chicago River, or just look down on it from your hotel room, it’s fun to count the number of different forms of transportation on and around it. You’ll see people on the adjacent streets and bridges walking, jogging and on Segway’s, as well as cars, buses, and the occasional horse drawn carriage. You’ll see elevated trains, part of the famous “L” system. But the real action is on the river, where kayaks mix with yachts and huge tourist boats, as well as the occasional jet ski. Look to the sky for a helicopter or a jet – and sometimes all these modes of transport can be seen at the same time, providing a sense of energy and movement. For some reason we haven’t seen too many bikers or motorcyclists in this area, perhaps showing that the natives have some sense – Chicago drivers are aggressive.

While the Chicago River cuts through the middle of the city and has plenty of attractions, Lake Michigan, not so much. The beaches have nice views, but a lot of concrete. If you’ve been to place that mixes the city and beach really well, like Rio or even Miami, you’re not going to be impressed by Lake Michigan. On the other hand, it’s an interesting mix of high density development with water views.

In the area of Millennium Park, if you’re lucky, as I was, you’ll stumble onto one of the occasional free concerts in Jay Pritzker Pavilion, including a wonderful celebration of dance I saw one summer night, which included the Joffrey Ballet, but the real stars were the break dancing group which earned a standing ovation from the crowd.

Hotels

The Godfrey is for the young and hip who don’t mind some noise. Suites are nice enough, not large, but beware of the noise from the 4th floor nightclub; they have a DJ every night and go until 2. The club has very nice views and, when not too crowded, is a fine place to have a drink, and an even better place for breakfast or just to hang out during day. While the evening crowd is young and good looking, it’s pretty tame, unlike say the rooftop at the Standard in LA, where, being LA, you’ll find girls in teeny bikinis and men smoking cigars – plus the view is much more dramatic than at the Godfrey. There are probably some people that meet at the Godfrey’s club to talk business, while the only kind of business done on the roof at the Standard is funny business.

The Godfrey caters to a young good looking crowd, not many kids in this group, lot of Europeans. Rooms are dark and not well lit. Staff is okay, nothing special. Very nice location and an easy walk to restaurants, Mag mile, river walk, or the lake.

But the best place to stay in Chicago is, as is often the case in my experience, a Kimpton – but be careful, there are 4 Kimptons in Chicago and the one you want is the Hotel Monaco. This is a truly outstanding location despite the fact that the immediate neighborhood is nothing special. But the Art Institute, Millennium Park, and Pritzker Amphitheater are easy walks, and if you get a river view room you can sit in large, really neat window nooks and overlook all the activity passing by on the Chicago River below you. This is a really pleasant way to pass the time as well as to see Chicago at work and play. The rooms have high ceilings, the lobby is fairly spacious if not grand, and the service is good. If you can splurge, go for a river view suite.

The Hotel Monaco’s affiliated restaurant, Water Street Grill, is nice, with decent food but somewhat spotty and inexperienced servers. Generally speaking, lots of dining options in this area, but few that are really outstanding. You’re better off walking across the bridge along Wabash and finding a spot on the other side of the river. (And in terms of burning calories off, a real gym, LA fitness, very large and with a wide selection of free weights and equipment is two blocks away from Hotel Monaco. $20 for a day pass)