Early May is going to be a busy time for Chicago. Around 20,000-30,000 technologists will be attending Microsoft's Ignite Conference May 4-8 . Let's not forget about the Azure/O365 Hackathon being run by ChicagosNext NFP on May 2-3. Outside of technology, the city will be flooded with visitors looking to parlay the Kentucky Derby with the Pacquiao/Mayweather fight into one big party.
Chicago is known to be a foodie destination with plenty of lists out there. The best part of doing a list like this is that the content is outdated garbage in less than a year. So let's experience what makes Chicago great...the neighborhoods..not the touristy areas on Michigan avenue.
Craft Cocktails: what are they and why the big fuss?
The Aviary won World's Best Cocktail Menu at Tales of the Cocktail. Make your reservations now.
Runner Up: Three Dots and a Dash is renowned nationally but Paul McGee has moved on to Lost Lake. Enjoy visiting the Logan Square neighborhood....which has no tourists and is far from the 'douche' vortex known as River North.
Runner Runner Up: If you are in the loop and don't have time to travel out for drinks, South Water Kitchen is possibly the only quality spot in the loop. Not to mention their bartender, Dan, just won RedEye's top Chicago Bartender of 2015.
You are tired/hungover/exhausted/hungry, don't want to leave the hotel.
I'm going to assume you are staying somewhere close to McCormick Place. Order delivery from Chef Luciano's. It happens, no one in Chicago is going to judge you for ordering delivery. We do it all the time.
You want a burger and don't care about the wait
Kuma's Corner used to be hot four years ago and tourists love saying 'cheezeborger' but no one here goes there anymore.
Visit Au Chevel in the West Loop, put in your name and phone number. Sit out the two hour wait at the neighboring bar Lone Wolf. Walk back when you are called and order the burger with bacon...and put an egg on it.
Runner Up: Scofflaw has an amazing burger that is better than the over hyped In-N-Out burger. Plus they make fantastic craft cocktails.
Chicago Style Pizza, you want that
Everyone in Chicago does not eat deep dish pizza, Nobody has time to argue about which places have the best pizza, just understand that whether it is deep dish or thin crust...both are better than where you live.
I've converted the most stubborn NYC style fans with Oven Grinders Pizza (cash only). Lots of locals love The Art of Pizza. And most of us eat thin crust pizza, cut in squares. Too many places to mention.
Just go somewhere and eat pizza in Chicago, don't over think it. I have ordered pizza delivery that is better than everything in Los Angeles.
You love people watching and want amazing seafood
Not only is it disrespectful to say that Chicago doesn't have good seafood but it is also uneducated. Go to the Viagra Triangle to people watch and stop over at Nico Osteria. If money is tight, then skip the seafood and stop over at the Lux Bar and order the fillet mignon sliders. (you would be surprised how cheap it is)
The weather is gorgeous and you want to experience Chicago outside
Rooftops seem like an great idea, but most of them have horrible drinks or overpriced food or attract the club crowd.
Head over to Parson's Chicken and Fish. Their backyard is huge, their food is amazing and they have a Negroni Slushy Machine. No further discussion on this.
It is impossible to create a list that covers it all. If this list made you open the map to discover areas outside of the Mag Mile....then I won. Thank you!