Pack Your Bags: Chicago

Your Best Day in The Windy City

Oh Chicago. Ever since I was a kid I've been visiting, and for as long as I can remember you've been my favorite city. That's a lot coming from someone who grew up in Boston. Chicago often plays second (or third) fiddle in the debate of best American cities, and it's a shame. It's Midwestern roots make the city appear less appealing than a Los Angeles or New York, but those same roots are what make Chicago amazing. Mainly: cheap beer, friendly people, and PLENTY of places to eat. 

You could certainly spend days exploring Chicago, but time is of the essence. And in the Midwest, Summer is the best time to go. Chicago Summers are like no other, so let me give you a rundown of the single best day you could have in the city (scroll over the photos to get my analysis): 

Morning: If you're a morning exerciser (I am not) you could wake up and take a nice run along Lake Shore Drive right next to Lake Michigan. Or you could get your start the right way, with giant Cinnamon Rolls. Head over to Ann Sather on Belmont to get your fix. They'll give you heaping portions for only a few bucks, so fill up. You can amble over to the Brown Line "L" a block away that will haul you downtown to the Loop.  

Mid-Day: Get ready for a flurry of activity. The Loop is filled with tourists so you have to make wise choices. As a rule of thumb I generally skip Michigan Avenue, but there are a couple of things that are must see. First, invest an hour and take an architectural river tour of the city. There are a number of companies that have boats, but my choice has always been Wendella. You get unparalleled city views and great rundown of Chicago's history. Well worth the $35 sticker price. 

After your boat ride you may be hungry, so stretch those legs with a 5 minute walk across Michigan Avenue to Bandera. The restaurant is slightly hidden on top of some shops, but that doesn't mean there won't be a wait. Well worth it for the best rotisserie chicken in the world. I know, roasted chicken isn't always a craving, but these birds are truly succulent. 

Did you booze during lunch? Well if you didn't (or did, whatever) you should zig back across Michigan Ave. to the Trump Tower. Chicago's newest controversial skyscraper has come with it's fair share of growing pains, but it's honestly one of my favorites. Even if you're not staying at the hotel you can still get up to the Terrace on the 16th floor. There you'll find an outdoor patio with overpriced drinks and pretty incredible views. You're not high enough to get a full city view, but instead you're amongst some of the classic buildings that define Chicago. Make it a quick stop though, the $10 beers don't pay for themselves. 

As you make your way back North you'll need to get one more viewing party in. Chicago is home to several very-high observatories, but the best is at the Hancock Building. Though not the tallest building in town, the Hancock is north of most buildings so you get a complete view of the city looking South. Just make sure it's a clear day, the clouds can move in pretty quickly off the lake. 

Evening: Here's where things get really fun. By now you're in the midst of happy hour, so you'll have to make your way back to the North Side. There are plenty of places to drink, but the best bar food in town can be found at Lucky's Sandwich Co. Featured on Man v. Food, Lucky's is home of the stuffed sandwich. Long story short, they put the french fries right in your sandwich. Yes, it's as good as it sounds. And if you can finish 3 of those suckers in 30 minutes you get your picture on the wall. Good luck with that.  

Once you're done with another meal I promise you'll be able to make the 2 block walk to your next destination, Wrigley Field. Depending on how deep into the summer you're visiting, it should be pretty easy to snag tickets to watch Chicago's lovable losers, the Cubs. While Fenway is still my favorite, Wrigley is a close second. The place is steeped with tradition and certainly lacking the luxuries that stink up newer stadiums. If you like beer and baseball, then this is your spot. I still don't understand the infatuation with the 7th inning stretch, but hey I'm not a Cubs fan. 

Late Night: Hopefully you paced yourself during the baseball game so you still have a little room left in the tank. Make sure you do a neighborhood tour of bars (including my favorites Justin's, The Schoolyard, and Southport Lanes) before one final meal. You can't go to Chicago without getting deep-dish pizza, right? Wrong. Take a stroll over to Dimo's Pizza on Clark to get excellent slices of normal pizza. The difference? They don't have a menu. Whatever concoctions they have on display are what's for sale, so feel free to get adventurous. Everything there is good, and your stomach will be thanking you for not eating too much dough after a long day. 


So there you have it. My favorite things to do in my favorite city. What do you think? Where else would you go? One thing I know, you won't out eat me in Chicago. It's just...not...possible.