Chicagopalooza! From Lily in Canada...

Today I have a special guest post from my friend Lily!  She has a great blog that you can access here:  Lily in Canada, basically she is hilarious and you should all check it out. Lily and I go way back, we grew up near each other in the Chicago suburbs, so I thought it would be fun for her to write a post about the best city in the world!  So, here goes!

It’s weird because I’ve been blogging for over a year and I still haven’t written about my home city of Chicago, Illinois. I say home city because I didn’t exactly live in the city. My hometown was about 40 minutes outside of the hustle and bustle. But I was close enough where I could go downtown and have weekend adventures and was able to return to the comfort of my own home. This post is going to serve as a guide of what my favorite parts of Chicago are. Kind of like Oprah’s Favorite Things except not at all like that.

Let’s start off with food. The problem with me is that I’m not picky. If I see a Cheesecake Factory anywhere I’ll just settle for that. The couple of times that I really wined and dined downtown I had other people paying for me. Otherwise I probably would’ve had a Jamba Juice and called it a day.  If you really want to impress someone, take them to dinner up at the Signature Room on the 95^th floor of the John Handcock building. On a clear day or night you’ll have the most amazing view of the city ever. The food is really good and the price is really high, but it’s worth it for the view.

If you find yourself on Michigan Avenue and are overly exhausted from all the shopping that you’ve done, pop into Ralph Lauren’s restaurant, RL. It’s attached to his store which is beyond amazing. Even if you don’t have the cash to dish out, it’s worth browsing. Trust me, you’ll feel like you visited a preppy wonderland. Again, this restaurant is pricey so I wouldn’t go unless someone else was buyin’!  If you have no money like moi, find the nearest Garrett’s Popcorn and indulge in the best treat of your life. The popcorn is literally dripping with toppings. You cannot go wrong with Garrett’s.

As for activities, I like to browse around The Art Institute every once in a while. This isn’t a staple activity for most, but I think it’s a cool place to be. It offers a surprising amount of famous works like Nighthawks, Sunday Afternoon on the Island of La Grande Jatte, and American Gothic. Even if you don’t particularly care for art, it’s worth it to list off the above mentioned paintings to your friends and family so you can feel smart for once in your life.  You should definitely visit The Bean and take a picture with it like everyone else in the world.

One of the best things that Chicago has to offer is Lollapalooza. This outdoor music festival is held every year during the first weekend in August. There are tons of good bands that play every year and in order to be a real Chicagoan you have to go to Lolla at least once in your life and never stop talking about it.  People often forget about this, but Chicago is the city by the lake. I hate when people say “Oh you’re from Chicago, huh? The Windy City!” I wish Chicago was known for other things besides its wind. I’ve been to windier places. Lake Michigan is really what the city should be known for. During the summer the sandy stretch along the lake is packed with sunbathers. It’s almost like a mini vacation. Navy Pier also gives off a summertime vibe that can’t be matched. Except for Coney Island and pretty much anywhere else that has a pier.

I hope this post was able to give you some good ideas for activities to do downtown. Chicago is a great, easy city with a lot to do. Just watch out for the Cheesecake Factory. If you don’t avoid eye contact, you’ll get sucked in.