Benson's Chicago guide for non-Chicagoans

Now that I've been in San Francisco for several months, many people have asked me about things to do and see in Chicago. If you're not fortunate enough get the low-down from me personally, here's a good reference on where to start.

When to go

Dressing properly is essential in enjoying the mid-western weather. Looking good while doing it is a whole topic on it's own.

• Spring - between mid March through May, the temperature may range from low 30F to low 50F. This is WARM (I'm looking at you, bay area and socal people)!
• Summer/Autumn - from May until late October, this may be the most fun time to go to Chicago. Look for events and festivals, like the Taste of Chicago during July 4th week, as there will be many things going on while everyone is packing in the fun before winter comes. At the peak temp, it may get hot enough to fry an egg on the asphalt. It's a matter of luck to avoid those extra hot weeks.
• Winter - The first snow usually starts around Halloween and the pulse of the city slows until Spring again. For those who have never experienced such temperatures, well, it's an experience. Bring your skiing gear and be prepared to wear it normally. For the fashionable, long underwear hidden away under your clothes is the way to go. Gloves and scarves are mandatory, and watch out for the slush on the edges of the sidewalk.

Getting around

Of all the cities I've been to, nothing welcomed me home like the Chicago skyline, easily stretching one's field of view. That said, the city is large not just in population, but also in area. For the normal tourist, the cab system in Chicago is very good: stick your hand up and a cab is there. Public transportation, better known as the Chicago Transit Authority, CTA, is decent as well. From either airports, a cab or limo service will cost about $50 and half an hour going into downtown, while the Blue line from O'Hare or Orange line from Midway will cost just $2, but suck up at least an hour going the same distance. The CTA trains are quite old; even the attempted clean up during the 2016 Olympic bid was less than successful.
It's important to note that there are some places a non-local, even a local, shouldn't be. Like all unsaid things in America, racial and economic segregation in more densely populated regions create areas that even the Chicago police don't venture into. I hope that this will not be true in the future, but as of this writing, all I can say is be smart when travelling. See the map below.

Get those deals

• CTA: 1 card and 1 fare takes care of buses and the "L" (any of the subways), don't need to ride the Pace buses. http://www.transitchicago.com/travel_information/fares/unlimitedridecards.aspx
• Attractions: http://www.citypass.com/chicago - just do it instead of going there unprepared.

Things to see and do

I've made gigantic list in google maps for location and planning reference. This list includes touristy bits, architectural bits, and some local flavor. Pick a couple things as it would take at least a week to hit everything, and I haven't listed everything either. Stick to the downtown areas if you haven't been there before, and venture out on your own. Most importantly, have fun!


View Benson's Guide to Chicago for non-Chicagoans, circa 2012 in a larger map

A shortened list of places include:

• Downtown
  • Sear's Tower, officially Willis Tower - 233 S Wacker Dr, Chicago, IL 60606 No self respecting Chicagoan will ever say Willis (unless paid to) except in the phrase "Whatcha talkin' about, Willis?".
  • Millennium Park - Cloud Gate, aka The Bean
  • Buckingham Fountain - Seasonal: Check to see if they turned the fountain on or off yet
  • The Art Institute of Chicago - Take your picture with the two lions in front
  • The Picasso - If you look at it from the front, it looks like a funny flying monkey. If you look at it from the back, you should see the profile of a women: the "wings" is her hair covering her face.
  • John Hancock Center - The other building with 2 anntenas on top
  • Navy Pier - Big tourist and local trap. Has a Beer Garden
  • Marshall Field's - Now owned by Macy's. The clocks on the building make it pretty famous.
  • James R. Thompson Center - Illinois Gov. builing. More Architecture.
  • Shedd Aquarium
  • The Field Museum
  • Adler Planetarium
  • Soldier Field - Chicago Bear's stadium. People say it looks like a spaceship landed on top of an old style arena.
• Lincoln Park/Wriggleyville
  • Wrigley Field - Iconic Home of the Chicago Cubs. Tons of bars around here.
  • Lincoln Park Zoo, Lincoln Park Conservatory - Flowers, and also can look back toward downtown
• Food
  • Chicago Style Pizza
    • Lou Malnati's Pizzeria
    • Giordano's Famous Stuffed Pizza
  • Hot Dogs
    • Portillo's Hot Dogs - Italian beef / Hot dogs and milkshakes. Lunch or dinner
  • MEAT!
    • Wildfire - STEAK! a bit more pricey and upscale side.
    • Carson's Ribs, Steaks & Chops - RIBS!!!
    • Harry Caray's Italian Steakhouse - Famous Cubs announcer's restaurant.
  • Korean - better than norcal, of course can't compete w/socal.
    • Cho Sun Ok Restaurant - Excellent Korean bbq
    • San Soo Gab San - late night korean bbq
  • Other notables
    • Garrett Popcorn Shops - Damn good popcorn.
    • Charlie Trotter's - You'll never get in here unless you book a year in advance. $$$$$
    • Alinea - You'll never get in here unless you book a year in advance. $$$$$