It wasn’t until I recently joined some travel groups on Facebook that I realized how much advice I give to people taking trips to Chicago. Like, how is your entire itinerary for a city that spans TWO HUNDRED AND THIRTY-SEVEN MILES just “eating deep dish pizza, going to Navy Pier, and shopping on the Magnificent Mile”? That’s less than 5% of the city!
So I decided to make a crash course in visiting The Windy City. Note: this list is not for everyone. If you don’t like spontaneity, exploration, and immersion, keep your itinerary and pay me no mind.
#1 – Venture Beyond Downtown
Downtown Chicago in simplest terms: huge buildings, tourist attractions, the riverwalk, museums, 1000 places to eat, stores I can’t afford, and the word’s largest population of taxi drivers with no regard for traffic laws or human life. Yes, it’s still worth the visit if only for the beautiful skyline, but it’s not going to give you a TRUE feel of the very depth that is Chicago. Here are a few additional neighborhoods I suggest checking out, if you have time:
Historic: Pullman, Hyde Park, Beverly, Old Town, Bronzeville, Irving Park
Bars/Nightlife: Lincoln Park, Wicker Park, Boystown, Wrigleyville, South Loop
Culture: Uptown, Humboldt Park, Chinatown, Pilsen, Little Village, Avondale (also refer to historic)
#2 – Avoid Touristy Crap
Pinch yourself for each of the following attractions you have on your itinerary: Millennium Park, Grant Park, Cloud Gate, Soldier Field, Art Institute, Willis Tower, Magnificent Mile, Navy Pier, Taste of Chicago.
Yes, all of these things are very nice, but there are far more exciting things to do in the city of 2.7 million people spread over 77 neighborhoods. I have too many suggestions to list them all individually (please refer to my Chicago Gems series), but I will tell you the best methods to find out about them yourself:
- ask a local
- browse MeetUp
- search Choose Chicago
- use Groupon, LivingSocial, and/or TravelZoo
- find cool-looking people and follow them (into events, not their homes)
#3 – Eat Like a Local
Yes, I know you really want to get deep dish from Gino’s East, or you wanted to try Michael Jordan’s Steakhouse. Just don’t. Why? Because when Chicagoans boast about how delicious our city’s food is, we’re probably talking about the little hole-in-the-wall on our block that sells Vienna Beef hot dogs and gyro burgers. Or our favorite vendor on the corner in Pilsen selling homemade tamales and elotes (aka Mexican corn) for $2 each.
So how do you find these places? Your best bet is referring to #1 and #4 in the section above, but I’ll graciously offer some of my classic Chicago favorites.
Harold’s Chicken, Portillos, I-57 Rib House, Home Run Inn, Uncle Joe’s, Cheesie’s Pub
#4 – Know What Not to Say
Never tell/ask a local any of these things. Why? No other reason than because it’s annoying.
- “Is it going to be cold?” – Is it summer? If not, yes. Or no. But probably yes.
- “It’s so cold!” – Yes, I know. But please tell me more about how warm it is back in your hometown.
- “Is it safe / Will I get shot?” – No it’s not / Yes. Now. By me.
- “Why is (insert thing here) so expensive?” – Hold on, I’ll ask my mom.
- “Have you ever seen (insert Chicago celebrity here)” – No. I have not.
And that concludes my crash course! How are you feeling? More confident? Are you pumped? Excited to see all of the great Chicago?! Good. Here are a few more bonus tips before I send you on your way:
use Divvy to bike around the city, it’s a cheap, fun way to get around.
say Sears Tower instead of Willis tower to anyone who looks over 18
don’t let anyone see you put ketchup on your hot dog
never ever take a Segway tour of ANYTHING. ANYWHERE.
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