How to See Chicago Like a Local.

Chicago is one city in America that I had always wanted to visit. I finally got that opportunity over the past Labor Day weekend. Lucky for me, I also had a place to stay in the Windy City, which meant the trip would be extremely affordable. This also meant that Lara and I got to see a completely different side of Chicago: that of a local. Here’s my advice for seeing the city as a local would, since that’s exactly how I spent my three days.

Lara in the park.

Head to Pilsen for some amazing Mexican food. We went to Nuevo Leon, and I suggest you do too. Not only is there a line out the door, but the home-made tortillas will make you feel as though you have never had tortillas until that very moment of your life. I had the asado de puero, pork marinated in ancho sauce and topped with onions and cilantro, for only eight dollars. It was one of the best Mexican meals I’ve ever had, and the price was more than reasonable for the amount of food I was given. After lunch, walk around Chicago’s Mexican-American community and listen to the Mexican music playing from a block party.

From here, take the Pink line to the Brown line and get off at Fullerton; you’ll end up in Lincoln Park. This area is home to DePaul University and even though you’re still in the city, you feel miles away. Grab dinner, coffee, or ice cream and window shop around town. Then head to the park to watch the families with kids and dogs frolic around.

Pilson "L" Station. September 2011.

I’d also suggest heading to Lake Michigan. Then lay out on the beach and if it’s warm enough, go swimming. Afterwards, find a place overlooking the lake to grab a beer and a bite to eat.

Then head to Wicker Park for some shopping and head to Alliance Bakery for some coffee and pastries. You can buy your treats and then head next door where there are plenty of tables and couches. It’s comfortable and a great place to stop between shopping. I highly suggest the Michelle: a peanut butter raspberry chocolate concoction and the flour-less chocolate cake. They are both delicious.

You can also spend some time downtown shopping. We headed to the theater district, around the Chicago Theater. This offered us some site-seeing, as well as some excellent shopping. There’s Zara and Steve Madden to name a few, and in the area there are several places to stop for a bite to eat. Unfortunately, it was raining the day we were there, but it would be the perfect area to spend a nice day shopping and eating.

As for nightlife, I’d suggest heading to Wicker Park, where there’s quite the selection of bars. We headed to Estelle’s, which had a great atmosphere and good crowd.

Picnic time!

Also in Wicker Park is Rainbo Room, which seems to be the hipster bar in the area. It has an interesting atmosphere and great music. If you want to go dancing all night, then Berlin on West Bellmont Avenue is the place to go. The gay-friendly bar plays a variety of music that’s perfect for dancing. There’s also a photo booth, that’s great for remember just how much fun you had that night on the dance floor.

Chicago is a diverse city with so many neighborhoods to explore. There’s no reason to stay downtown when the rest of the city has so much to offer.

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