Welcome back friends! Our second edition of trip of the week has us heading to the midwest for an iconic stadium among two other great events.

Trip Details:

  • Location: Chicago
  • Dates: August 12-14, 2016
  • Days: Friday – Sunday
  • Events: PGA TOUR, MLS, MLB
  • Weekend Wild Card (WWC): NFL.. kind of & Toby Keith

Airports available:

  • MDW: 30 minute train / cab
  • ORD: 45 minute train / cab

The Windy City! Chicago has a TON to offer to any and every one. If you can’t have fun here you probably should hand over your life savings to me. I’ll use it better. Fresh out of the box we get to go to Wrigley Field on Friday afternoon. My (second) favorite ballpark. The Cubbies take on in division rival St. Louis Cardinals for a mid afternoon game.

The Family at Wrigley
The Family at Wrigley

If you’ve never been to Wrigley, prepare yourself to feel like a kid in a candy store. It’s a baseball lovers dream and even if you have no sense of history, you can tell a lot has gone down here. The Cubs are famous for not having won a World Title since 1908. You’d never know it based on the crowd turnout. It’s partially because they’ve been around for so long but also because the White Sox don’t have much going for them either.

From the ivy to the manual scoreboards in the outfield everything just feels like a dream. Only recently have they added an electronic scoreboard to try to get with the times but it almost feels out of place. What’s most interesting are the outfield bleachers. I mean, the ones outside the stadium. There’s literally rooftop bleachers on top of bars.. across the street. 500+ feet away from home plate and yet just as much fun and half the cost.

Some places to check out before and or after the game are the Cubby Bear, the iconic bean (your standard instagram photo op), and Gibsons steakhouse (only if you aren’t buying)IMG_8289. For those that watch The League on FX, this is the gangs home base. You can also head up Trump Tower or for you liberals out there you can scope out the Willis Tower. Both offer equally exhilarating views.  For pizza, I’ll let you decide. Your ole reliable’s are Lou Malnati’s and Giordano’s.. but there’s hundreds more to choose from. Why not explore and find a hidden gem? Last but not least the Lincoln Park Zoo which houses over 1,200 animals.

Saturday is for golf. Moving day in Silvis, IL at the John Deere Classic. Fun fact: they have the best tee markers in the game. I’m being serious. Literally little tractors on every tee box. Silvis is a good 2.5 hours away. If you happen to be driving in from anywhere west of Chicago, it might be worth flipping the Cubs game with Friday’s round of the tournament. The John Deere Classic is hosted on TPC Deere Run (fittingly) and Steve Stricker has dominated this course. Jordan Spieth took home the hardware in 2015 in dramatic fashion.

Tee-Markers-e1373912643611Venture back to downtown and grab a Goose Island IPA at your hotel bar. Sunday’s sporting event is an MLS game featuring the hometown Chicago Fire facing Orlando City FC. Tickets on Stubhub are hovering around $30-40 and scalping will probably get you even farther. By this point you’ll have become familiar with the ‘L’ train getting you all over town which you’ll utilize to get to the game if you don’t have your rental car anymore.

If that all wasn’t enough for you there’s two other notable events in town. DA BEARS have a preseason game against the defending Super Bowl Champion Denver Broncos on Thursday evening prior to our great weekend. Or on Saturday night Toby Keith is performing at Hollywood Casino Amphitheater in Tinley Park. Head on out to Chicago and let us know how your trip of the week went!

A famous Chicago dog.
A famous Chicago dog.

To create your own action packed weekend, use our filter/search function in our master calendar and see what you can put together!

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