My Kind of Town: Top 12 Things To Do in Chicago in 2013


As I’ve mentioned before, leaving Chicago (one of the arguably coolest cities) is both sad and exciting. A lot of people have come to visit in the eight years I’ve been here and seen the majesty that is the Windy City… and for that, I’m thankful. This post isn’t for them, though… this post is for anybody who comes to Chicago AFTER I leave. No one is going to wind up at Navy Pier on MY watch! Although everyone in Chicago will have a different answer, here are MY Top 12 Things to do if you happen to be fortunate enough to find yourself in Chicago! For the city is so awesome that a top 10 list could not contain it.

  1. Hot Dougs– As you can tell by the clever name, Hot Dougs is a “Sausage Superstore and Encased Meat Emporium.” But this is no ordinary hot dog joint.  I always hesitate telling ANYONE about Hot Dougs (especially the interwebs) because  it inevitably makes HotDougslogo_mediumthe line to get in that much longer. But for you, dear reader, I’ll make an exception. Doug Sohn, chef and hellofaguy extraordinaire helms the register and makes elevates the hot dog to a state of gourmet godliness. To give you an example, here is an item from this week’s menu of specials: Portabella Mushroom and Swiss Cheese Pork Sausage with Sage Mustard, Smoked Blue Cheese drizzled with Honey and Shiitake Mushrooms sautéed in Duck Fat. You would expect something like that to be crazy expensive… and yet, at Hot Doug’s it is only $8. Try and hit it on a Friday or Saturday when Mr. Sohn fries his French fries in duck fat. I don’t know whether to be proud or embarrassed, but Doug actually knows my name and how to spell it… so, yeah… I kind of love that place.
  2. Museums- Chicago has some of the most amazing museums in the country. The Shedd Aquarium is one of the countries oldest aquariums and boasts some of the coolest vintage fixtures. The Museum of Science and Industry has an actual German U-Boat that you can tour. But, the crème de la crème is the Art Institute of Chicago. I’ve been to some museums in my time, and the Art Institute is probably one of my favorite. When I took Russell to visit a few summers ago, he was floored by how many “famous paintings” there were. It is an amazing collection housed in a great space and if you only have time to see one museum, make it this one.
  3. Grant Park- Grant Park is a green space that encompasses everything East of Michigan Avenue from Randolph St. to Roosevelt. Within this park is “The Bean”/Cloud Gate, CloudGate-010Buckingham Fountain, the Pritzker Pavillion, and a huge expanse of beautiful statuary and nature. I love that, even for a large urban area, Chicago really puts an emphasis on public art and green space. Grant Park hosts a myriad of fun things to do in the summertime, from Lollapalooza and Summer Dance to Taste of Chicago.
  4. The Rick Bayless Empire- Chicago is a food town and hosts some of the finest restaurants. But one that I really think is a “cant miss” experience is any of the three restaurants housed in one section of a city block that belong to Rick Bayless. Rick Bayless is an American chef who made his fame on PBS hosting a cooking show dedicated to authentic Mexican food. What is beautiful about his restaurants is that no matter your price tier, he has an option for you that is mind-blowingly delicious. Additionally, he is a huge believer in local farmers and even has his own garden on the roof of the building.
  5. Comedy/Theater- I was lucky enough to be involved in a small way in this scene and I encourage everyone to check out at least one show when they come to town. I always joke that Chicago is like grad school for comedians- it is a place where a lot of famous people have honed their craft before exploding into stardom. Not only is there The Second City, and iO (Improv, but the independent comedy scene and standup world are exploding there, as well. If there is a Blewt! show running, check it out and if you want to see the future of stand up, head to Chicago Underground Comedy. There is also the NeoFuturarium and the legitimate theater powerhouses of The Goodman Theater and Steppenwolf. Chicago also boasts a legitimate Broadway-esque theater scene that previews some of big shows that find their way to New York.
  6. Wrigley Field- If you are a baseball fan (or, even if you aren’t) catching a game at Wrigley cubsField is special. There is just something magical about a sports venue that storied and steeped in tradition. Even if you just drive by it, it’s cool to see something that you’ve grown up seeing on television and in movies.
  7. The Architecture Tour- It always amazes me to see the contrast between Chicago and Atlanta– two cities that burned down and were rebuilt at roughly the same time. It is amazing the impact of having money and resources can do. Chicago has some of the most beautiful architecture from all different periods and it is fascinating to explore. They offer a great architecture tour that goes down the Chicago River that is filled with fascinating factoids. And, although the Sears/Willis tower is the tallest building in America, you pay a premium to go to the observatory… lemme give you a hint… there is another super tall building at the other end of Michigan Avenue called the John Hancock building. And although you ALSO have to pay money to get to the top of this building, they have a bar/restaurant called The Signature Room that is on the floor below the top floor where you can get the same view, without an admission cost AND get a drink.
  8. Michigan Avenue- And speaking of architecture, I would be remiss if I didn’t point out walking down Michigan Avenue. Although it is a high-end retail strip, in all of my years there, standing on Michigan Avenue as it crosses the river never ceased to amaze me. To be at the apex of city and feel its pulse is intoxicating and never lost its sense of awesomeness. There is a reason why large swathes of the latest Batman franchise were shot in Chicago… it is Gotham. I’m not a huge shopper, so the retail stuff is a little lost on me, but it is a thrilling walk no matter your reasoning. Standing between the Wrigley building and Tribune Tower, looking down Michigan (either way) is jaw dropping.
  9. Public transportation- I know this sounds silly, but as someone who grew up with Marta elin Atlanta, the fact that Chicago actually has a vast and functioning public transportation system is awesome. Yes, you will always run the risk of running into hilarious nut-cases on The El, but it is totally worth it for the experience of seeing how public transportation SHOULD be. Plus it gives you a different vantage point of the city… and it costs $40 less than taking a cab from the airport!
  10. Chicago Pizza- Chicago Pizza is unlike any other pizza you will find, well, anywhere. It is a super-dense, super-deep, colon-buster of deliciousness that is worth your time. Avoid the “famous” Uno’s or Duo’s and hit a Lou Malnati’s… the wait will be short and the pizza will be just as delicious.
  11. State Street- State Street especially between Lake and Madison is neat to experience Chicago Theaterbecause it houses both the Chicago Theater (which I grew up seeing on WGN) and the old Marshall Fields (which is now a Macy’s). If you have a chance, explore Macy’s and have lunch in The Walnut Room for a bygone era experience. It is one of America’s oldest department stores and seeing retail ensconced in lovely architecture makes the strip malls in suburbia seem silly. Also, if you forgot something from home, swing by the new Target that they placed in the beautiful reclaimed Carson Pirie Scott building.
  12. Lake Shore Drive- When Chicago was growing, the string pullers decided that the lakefront should never be residential and that it should always belong to the public. That is why you will find beaches, parks, and Lake Shore Drive on the coast of Lake Michigan as opposed to more high rises. I had never seen a lake so big that you could not see the other side before until moving to Chicago and taking a drive down Lake Shore Drive is amazing.

I’m getting a little misty writing about Chicago as I sit in California. There is a specialness to every place, and I look forward to discovering all that California has to offer… but Chicago just has something special. I’ve told Jojo many a time during this process that if West Coast living doesn’t work out, I will gladly move back to Chicago and call it a day- no more roaming for Leigh. So, do yourself a favor, and visit… you wont regret it… unless you go to Navy Pier. NEVER go to Navy Pier. 🙂 bench shotsignaturepinkreal

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  1. I recently learned (by meeting someone who was training to be a docent) that the Chicago Architecture Foundation actually offers dozens of tours in various neighborhoods in Chicago, so I thought I’d drop a link to the actual boat tour (which has split into a few flavors now too, I see): I heartily second this recommendation. It is the one thing I always tell visitors to do in Chicago. My late FIL the architect was impressed by the level of knowledge displayed by our docent when we took the tour together years ago.

  2. You had me at number one with the hot dogs. I truly regret not visiting you while you lived there. And now your life adventure has taken a new turn- for another great city that I have never visited. Bub, Baby Bub and I will be making a trip to (the other) LA to visit after y’all have had time to settle and find a new set of must sees. I do have the number to Pink Dot if you ever need it.

  3. Just like Coralie I am so sorry I let you get out of the Windy City
    without getting there. Yet and however, I feel like I did. You make it sound so good. My only recommendation and I think it is non ezxistent now was to have a two and ahalf inch filet, medium rare, at the Stockyard Inn,,,MMMMMMMMMMMMMso good.

  4. There is a specialness to every place, and I look forward to discovering all that California has to offer… but Chicago just has something special. I’ve told Jojo many a time during this process that if West Coast living doesn’t work out, I will gladly move back to Chicago and call it a day- no more roaming for Leigh.

    Why not have both, like Steve Harvey?

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