I couldn't write a guide book, but I could tell you a thousand stories (Chicago)

Member Name: jamesontheroad

Product:	Chicago
Date:	21/01/09 (30 review reads)
Rating:

Advantages: Cheap to explore and enjoy, immense variety of neighbourhoods, lots of culture and entertainments

Disadvantages: Summers very hot and humid, winters very cold. Without local knowledge the suburbs can be daunting

The sheer enormity of Chicago makes this a difficult review to write. I can only hope to think of the great DooYoo reviews that offer some personal insight to the subject, so forgive me if this is not so much of a helpful travel guide as a series of unrelated recommendations for a briefly adopted Chicagoan! In that respect I strongly recommend the Lonely Planet and Time Out guides to the city, and also the immense amount of user-generated information on the Chicago pages of Wikitravel:

http://wikitravel.org/en/Chicago

There's so much there in fact, that Chicago was one of the first Wikitravel destinations to be developed into a printed book (although I would continue to recommend the more up to date and completely free website over their book).

I've visited Chicago about half a dozen times, always staying away from the downtown either with local hosts or, more recently, my partner who spent three years living in the city's Uptown and Logan Square neighbourhoods.

Most people arrive in Chicago by plane, either at the larger international airport at O'Hare or the smaller and primarily domestic terminals of Midway. But my most memorable arrivals have been by train, reaching the city in the mid morning by the reliably unreliable Amtrak Lake Shore Limited train, which provides daily overnight service between Chicago & New York City, with a portion of the train dividing/connecting en route for Boston. Leaving New York City in the early afternoon (or leaving my old home in Montréal in the morning, for a connection en route) this train travels up through New York state and through Ohio to Chicago. I've woken up to see the rural fields of Ohio rolling by, and have always been captivated by the first glimpse of Chicago's skyline. The southern approaches to the city are not pretty: heavy industry, ugly lake front casinos and deprived south side neighbourhoods don't sell the city, but they do tell a slice of its remarkable history. Nothing builds the excitement of Chicago like this train does for me, and if there is one absolute recommendation to those considering a trip to Chicago, seriously consider combining a trip to New York with one to the Windy City. Fly in to one and out of the other, with the train in between: you will truly understand what makes these two grandest of American metropoli different.

For me, that difference relates to Chicago's geography and it's people. New York is full of people of all nations and all colours, but they have all come to that city from disparate places, and they're all fighting for a piece of the space. Chicago has a dense downtown core named after the 'Loop' of elevated train tracks that encircle it, but climb to the top of the publicly accessible sky scrapers and you'll see that in fact there is no pressure in terms of space. In fact I'd recommend the John Hancock tower over the slightly taller Sears Tower, because although it's shorter it's located further north from the Loop and offers a much beter view of the cluster of Loop skyscrapers (and the bar is free to enter as long as you have a drink). Lake Michigan provides the eastern edge of the city, an almost perfect north south line against which the city sits. In the opposite direction it just flows away towards the seemingly endless prairies. This is a mid-western city, and many of the people you'll meet here who weren't born in the city have come from the mid-western states. They have a close association with the rural heartland of America, so Chicago is both a dense urban centre and a hub of people who yearn for the countryside.

That countryside is not difficult to access, but it can be slow. If you have time or, like me, make repeated visits, consider road trips round the bottom of Lake Michigan to the state of the same name. Head north past Milwaukee to Wisconsin, or even north-west to Minnesota.

For many Chicagoans that countryside bears no relation to their city. It is with no small pride that Illinois sent it's governor to become the country's first black president. To this day many districts, notably parts of the south side, remain almost exclusively black and in many cases remarkably impoverished. Outsiders should not be intimidated, and if interested in this part of Chicago's history you should head south to the district of Bronzeville and the DuSable Museum of African-American History.

My favourite museums include the Art Institute for its immense collection of modern and classic art. Near-by the Chicago Architecture Foundation organise walking tours of the city and boat tours during the summer. This is the city of the skyscraper, and these guided tours are real eye openers. The Field Museum is a must for families and the Museum of Contemporary Art has an world class programme of modern art.

Beyond that? My advice is to explore. Winters can be unbearably cold but then high summer can also be stifling, so time your trip right around the shoulder seasons. I've had dozens of fantastic walks, many miles long in some cases, and not just around the tourist-centric neighbourhoods. The Magnificent Mile is great for shopping, but when the crowds become too much you should consider jumping on a train or bus to reach the friendly near-north or up town neighbourhoods. If you have the energy and want a big walk, I've enjoyed striding up the length of Milwaukee, one of the city's few diagonal avenues that bisects so many interesting and different neighbourhoods. Make the cluster of streets around the intersection of Milwaukee, Damen and North your destination, and try some of the excellent coffee shops and bookstores.

Finally, get familiar with the creaking but ultimately reasonable CTA (Chicago Transit Authority) system. The trains are old and slow, and the buses only run to a vague aspiration of a schedule, but day, three day and week cards are great value, and the blue line provides a direct (if very slow) connection to O'Hare airport. Bus lines follow major streets and are named as such. A useful city map with all the lines is available from larger CTA stations.

Chicago is my favourite American city, but it only became so when I struck out and explored it on foot and by CTA. Enjoy the tourist hubs, but ask for and take personal recommendations, and you'll receive more tips than I can possibly give you here. There's so much to see, and so much of America's history to discover.

Summary: Best sampled immediately after New York City, and then repeatedly