Chicago: a starter guide to the Windy City

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Welcome to the Windy City! While Chicago’s nickname is courtesy of the blustery weather, it’s the heights that it should be known for. Home to towering skyscrapers and sky-high spending sprees, this town was built to exceed expectations. Here you’ll find the essentials for raising the bar on your own trip to Chi-town.

Millenium Park– the playful heart of the city is alive with public art

  • Cloud Gate - aka 'The Bean', is Anish Kapur’s brilliantly polished 110-ton sculpture that is undoubtedly the park’s biggest draw
  • Jay Pritzker Pavillion - designed by renowned architect Frank Gehry, the pavillion is a 120ft-tall band shell that towers like a metallic crown over the park
  • Crown Fountain - designed by Jaume Plensa, this 50ft-high water sculpture projects images of Chicagoans spitting out water onto squealing children (and sometimes adults) below

Pizza – there’s deep love for this deep dish

  • Pizzeria Uno - this is the original PU location, on E Ohio Street, where it's said that deep dish pizza was invented; a medium pie will feed a family of four
  • Giordano’s - possibly the best pie in Chicago - order the 'special', stuffed with sausage, mushroom, green pepper and onion, and decide for yourself
  • Gino’s East - so good you’ll want to take one home with you - and you can. They ship!

Architecture – out of the ashes of the Great Fire of 1871 rose these edificial phoenixes

  • Monadnock Building -  the largest office building in the world when completed in 1893, its internal steel frame gave rise to the skyscraper
  • Auditorium Building - one of the best-known designs of Adler & Sullivan, of the ‘Chicago School’ of architecture, the Auditorium was declared a National Landmark in 1976. The building now houses the Auditorium Theater, the resident home of the Joffrey Ballet.
  • Robie House - designed by the nation’s great architectural mind, Frank Lloyd Wright in 1909. The striking horizontal lines of the home, inspired by the flat Mid-Western landscape, exemplify the ‘Prairie School’ movement.
  • Chicago Architecture Foundation River Cruise - see the city and many of its architectural masterpieces from a unique perspective - aboard a river boat cruise

The Magnificent Mile – every shopaholic needs a little retail therapy now and then

  • Filene’s Basement - elbows out, ladies: everything in this famous discount department store is 30-60% off. 'Running of the Brides' takes place once a year, where brides can save thousands of dollars on a gown. There’s a reason the moniker is reminiscent of Pamplona…
  • American Girl Place - make your little girl’s dream come true at this doll emporium - it will only cost you $100 for the doll, $32 for her swimsuit, $18 for her camping equipment, $54 for her china tea set… If you don’t break the bank on the dolls alone, there are always dining options, in-store party planning, and seasonal events.
  • The rest of it - everything else your little heart desires: Bloomingdale's, Nordstrom's, Macy's, Neiman Marcus, Saks, Gucci, Armani…

Further information

For more on what to do in Chi-town check out these great ideas from the Thorn Tree travel forum.

Related article: Travel on a shoestring

This article was originally published in August 2009. This article was refreshed in August 2012.