What NOT to do in Chicago
In a city as big as Chicago with so much to offer, it's easy to get caught up in all the touristy garbage you're told you "have to do". After being in Chicago a second time it was easy to avoid all that nonsense and I couldn't have had a better experience because of it. Here's my list of what you SHOULDN'T do (and what to do instead) while in the Windy City.
DON'T: Go to the Willis Tower
DO: Grab some cocktails at the Signature Room at the John Hancock instead.
Why? For the same price you can enjoy the same (if not better) views with a fancy overpriced cocktail in hand at the lounge. From 1000 feet up on the 95th floor, you can see up to 55 miles out and four states (or you're supposed to at least). But in this case, I'm just here for the booze.
When to go: when there's no fog. Don't make the same mistake I did, kids.
Don't eat a hot dog with ketchup. It's sacrilegious
DO: eat Chicago dogs the right way- topped with mustard, relish, a dill pickle spear, tomatoes, white onion, celery salt & sport peppers.
VEGAN/Veggie tip: I got my vegan version of the iconic Chicago Dog at Kim & Carlo's Hot Dog Stand : serving up the best veggie & non-veggie dogs in town.
DON'T fill up on Hot Dogs & Pizza
DO: check out the city's chef scene.
Chicago is crawling with culinary geniuses serving up some of the best food you can find in America. Home to various Michelin starred restaurants, Chicago sets the bar high when it comes to food & drink, so it only makes sense you either snag a reservation at one of the famed establishments, or have Chicago's #1 private chef, Chef Charles Webb, cook up a delectable meal at the location of your choice. Our friends at the Trump decided to spoil us with a gorgeous view. **cue cool emoji with sunglasses** More on our delicious afternoon soiree HERE.
- DON'T book tickets in the Theatre District
- DO: book tickets for a comedy show.
- Save the Broadway shows for Broadway. Chicago is the birthplace of improv & the place where SNL goes looking when it needs to replenish the well. 'nough said.
- Favorite comedy joints include but not limited to: Zanies, Second City, iO Chicago.
- DON'T go to the Navy Pier
- DO: ride bike along the lakefront, and the rest of the city.
- DON'T spend your entire stay Downtown
- DO: spend part of your stay in a local area
Chicago is a big city made up of a bunch of different neighborhoods, each with it's own character. If you don't experience the eclectic culture while you're here, you miss out on the essence of what makes this place one of the greatest cities in the country.
Stay at a hostel, ride a bike to the nearest coffee shop, talk to locals, engage. You'd be surprised at how much you learn.
My favorite areas: Bucktown, Wicker Park (near Damen Ave), Lakeview, Park West