Chicago: a starter guide to the Windy City

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.

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