Six tips for Chicago newbies

Fellow blogger and new Chicagoan Angelawd kindly gave this blog a shout-out a few months ago, calling it her “Chicago manual.”

Why thank you, thank you very much.

Instead of letting this go to my head, I’ll use it as inspiration. Truth is, I wish someone would have given me a manual when I moved to Chicago five years ago as a starry-eyed girl seeking a new adventure in a new state. I was clueless. I made my own manual along the way, and interestingly enough, just realized that many of the same rules apply even when you move to new neighborhood.

Here are a few things I wish someone would have told me when I arrived to Chicago (And yes, I know lists typically come in fives or tens, but since this is not work, and you’re my client in this moment, I hope you don’t mind).

1. Make friends with the CTA

The CTA is your best friend and worst enemy. One day, it will get you home quickly and safely without a hitch, and the next day, it’s a prankster laughing maniacally as you wait in the freezing cold or arrive at your destination heinously late. But we are lucky to have this frenemy at our disposal. It certainly saves on costs for a car and parking. Get to know the CTA lines and the schedules. And don’t be embarrassed if you take a train in the wrong direction. It happens to the best of us.

2. Make friends. Period.

Chicago is more fun with friends. Maybe you’re one of the lucky ones who moved here with a ton of friends already at your disposal. I had three. So, as you can imagine, throwing a dinner party was challenging.

Making friends isn’t as hard as it seems. Start by scouting out your prospects at work. Joining clubs like I’m running for prom queen has also been good to me. Some of my besties are those in my wine club. And I’ve met some really smart, funny women in book clubs. Volunteer, play a sport, start a club. Just be where people are.

3. Celebrate the eccentricities.

Weird, ridiculous events are inevitable.

You’ll see cats on a bus, witness crazies fighting, get called a liberal lesbian on the Red Line for no reason, go to the wrong airport and miss your flight, or get drunk and introduce yourself to celebrities. Or maybe that’s just me.  I’ve learned to embrace and laugh at all the oddities that comes with city living. It’s part of what makes it so interesting in my book.

4. Find your local drinking hole and go-to restaurants.

It’s cold in the winter. You’ll need a place to drink away your regret for not moving somewhere warmer. You’ll also need a Thai restaurant on speed dial for the nights your cabinets are empty or it’s too damn cold to go outdoors.

5. Scope out free and cheap things to do

Chicago is expensive. For the price paid for rent, we could own two houses elsewhere. That fact would be depressing if there weren’t lots of rad, free things to do here. Time Out Chicago was my urban bible the first few years we lived here. Also, The Reader and Gapers Block are good sources. (Duh, you probably already know this.)

6. Get out and do that stuff.

The best way to get acquainted with this city of ours (or any for that matter) is to get off the couch and explore. There are so many things to do that it’s hard to wrap my head around it. Even in five years, there are tons of things I haven’t gotten around to doing. Here are just a few things to do:

Act like a tourist.

Go to a game.

Take a class.

Go to a BYOB restaurant.

Explore other cultures (or Americanized versions of them).

Go dancing.

See a show.

Of course, you can also go the museum, hang out at the beach, hang out at a park, take in a summer festival, join a sports league, watch a parade…and the list continues.

Go ahead, get out there and soak it all in.



Filed under Chicago, city life, random

6 responses to “Six tips for Chicago newbies

  1. sarah

    I cannot stop laughing when I think about you getting drunk and introducing yourself to John Cusak. And also the picture of Megan and Justin dancing.

  2. Also, explore different neighborhoods across Chicago! Check out our site for people who are new to the city:

    We liked your post and tweeted it out today!

  3. Thanks for the shout-out and the tips! Keep them coming, I certainly need the help.

    My next post will be about CTA crazies. 🙂

  4. Denise

    My picture has made your blog twice now! I am humbled and honored 🙂

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