i've received quite a few emails in the last year asking me the best things to do, restaurants to eat at, places to see, areas to shop, and so on, in Chicago. although i've lived here for a year, i still feel like there's so much left for me to explore and discover!
if you want to be a true tourist, here's what you should see/do:
Millennium Park + the 'bean'
Water Tower Place
John Hancock Observatory (360 Chicago)
Lincoln Park Zoo
Sears Tower Skydeck (i refuse to call it Willis Tower)
The Shedd Aquarium
The Museum of Science and Industry
The Field Museum
North Ave or Oak St Beach
best places for shopping (in my opinion):
State St (south of the river, in the loop)
Water Tower Place
900 North Michigan Shops
Armitage Ave + Halsted St (Lincoln Park)
intersection of North Ave, Damen Ave, and Milwaukee Ave (Wicker Park)
best places for restaurant options (if you want to walk around and pick a place):
Broadway St (Lakeview East/Boystown)
some of my favorite restaurants:
Green St Smoked Meats (West Loop)
Ann Sather (Lakeview)
Las Fuentes (Lincoln Park
Antique Taco (Wicker Park)
Wilde (Lakeview East/Boystown)
Homeslice (Lincoln Park)
Pastoral (Lakeview East/Boystown)
Epic Burger (chain - many locations)
you MUST eat Chicago-style pizza. MUST. here's my ranking of options:
Lou Malnati's (i would eat it once a week if i could)
you also must eat at Portillo's and you must order a Chocolate Cake Shake
make time for a game, concert, or other show
sports, comedy, and music are a shared love. make time to take in a Cubs or Bulls game. go to a comedy club for a night. see who's performing in the city during the time you'll be here and buy tickets! if you can't find anything else, try going to a Blue Man Group show - it's entertaining and in a cool theater.
know where you're going/have a plan
there's so many places to see, so many things to do, and so many restaurants to eat at that it's best to have a rough idea of what your day will look like before heading out the door. map it out so that you're not spending more time traveling to places than you are experiencing them. not to mention, there's few things that are more annoying to Chicagoans than tourists standing in the middle of a busy sidewalk with a map opened.
ask for help!
although we may not all look eager to help, we probably will. if you're lost or can't seem to find a certain intersection/place, ask someone on the street. they should know how to give you directions. if you can't find a willing soul, step in a restaurant or business and ask an employee.
use public transportation
the subway system (what we Chicagoans call the 'el') is easy to navigate, cheap, and will get you just about anywhere you need to go.
wear comfortable shoes/clothes
since you'll probably spend most of your day standing and walking, it's important to wear shoes that can last all day long. there's nothing worse that getting an hour into your day and realizing you chose the wrong outfit for your activity.
this is sort of a joke, but also not. those of us that call Chicago home tend to walk about 2.5 times faster than the rest of the people in the city. i think it's due to the fact that we have to walk fast during the winter to get out of the bitter cold, so it just becomes part of who we are.
consider the time of year before you come
while the winter is beautiful in the city, it's cold. like, real cold. if you're hoping to do things outside and walk around, consider coming in late spring or early fall. if you want to hit up the beach and possibly sweat a lot, come during the summer! if you want to know what it's really like to live in Chicago, come in January. then you'll never come back ;)
(this is certainly not a complete list of all of the wonderful things Chicago has to offer, but it's a start! spend some time doing online research for a more complete view of the city!)