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KSR Travel Guide: Chicago

In just a few days, thousands of our closest friends and neighbors will travel to blistering cold Chicago to watch Kentucky play a basketball game. The Cats will meet the Bruins of UCLA in the second contest of the CBS Sports Classic double-header, set for an approximate 2:30 pm tip local time after the opening act. The midafternoon start time is ideal for those in Big Blue Nation looking to enjoy the city — or get oiled up before the tip and afterward in celebration.

Tonight, as we count down the days until #wheelsup, allow me to share some facts and recommend a few activities for your weekend in the Windy City. You have a lot on your plate this week, so leave the research to us in this KSR Travel Guide to Chicago.


Fun Facts

The “Windy City” nickname is a reference to politics, not actual wind.

However, it’s really windy in Chicago. I remember walking across a bridge around this time last year and thinking I might die from the violently cold wind hitting my face. It’s uncalled for, really. They should do something about that. Nowhere should be that cold and windy. It’s not healthy.

So be ready for that.

The Sears Tower is now the Willis Tower but it’s still the Sears Tower.

Once the tallest building in the world, Chicago’s Sears Tower is the unofficial logo for the city. It’s name was changed to the Willis Tower in 2009 but the locals will throw you in the river with cinder block shoes if they overhear you call it anything but the Sears Tower.

Spray paint, the zipper, the Ferris wheel and the Twinkie were invented in Chicago.

Chicago was also the birthplace of Playboy magazine. I cannot confirm if its creation and the invention of the zipper are related or a coincidence.

The Chicago River is the only river in the world that flows backwards.

Engineers reversed the flow to protect the city’s water supply and settle increasing sanitation concerns. They did so by forming a human dam with 2,700 volunteers treading water and pushing the current backwards with their hands. Several of the volunteers drowned in the 12-hour reversal process but the city honored their service by engraving their names in the 800-block of the Magnificent Mile sidewalk. (I completely made that up. They probably used canals and lots of math and stuff.)

What To Do

Go to Vincenzo’s Sports Tavern or The Pony before the game.

Vincenzo’s became an unofficial UK bar before the Champions Classic last year and they’re running it back again on Saturday. They will have food and drink specials for Big Blue Nation and a free shuttle to and from the United Center.  Vincenzo’s is on West Madison Street, about one mile west of the basketball.

The Pony is the official spot for UK alumni and basketball fans in Chicago. It’s the place to watch the game if you don’t have tickets and they’ll be partying before and after as well. The Pony is farther away from the United Center but I believe they’re offering a bus ride too.

Grab dinner, a drink and possibly something you can’t get rid of in the Viagra Triangle.

The Viagra Triangle is a neighborhood known for its creepy old men wandering around restaurants, bars and clubs looking for a young lass who likes a good credit card limit. Gibson’s is the heart of the area and where I will be dining Friday night before I retreat back to civilization a little further south.

Ask people about Anthony Davis.

Who knows, maybe you’ll find an old teacher or an ex-girlfriend, maybe someone who knew him when was a normal-sized human with glasses. Just ask around and see where it gets you.

The Santa Booze Cruise with all of my idiot friends.

I have a group of 40 boarding the Anita Dee II Saturday night for a three-hour cruise on Lake Michigan. The yacht holds 400 people and we’ll all be wearing Santa hats and making questionable decisions. Tickets are still available if you’re interested.

Let’s go. GET IN THERE.

What Not To Do

Put ketchup on your hot dog.

Asking for ketchup at a hot dog stand is a surefire way to get your ass kicked. It’s a rookie move, a slap to the face of the cooked sausage. You know that guy who pours a liter of Coca-Cola in his bourbon? That’ll be you if you put ketchup on your hot dog. Don’t be that guy.

Fly in or out of O’Hare.

Chances are you’re already locked in to your travel plans at this point, so you’ve either dodged or committed this brutal mistake. O’Hare is universally known as the worst airport in the world during the winter, supported by a Chicago Tribune report saying 42 percent of flights are delayed in winter months. Sure, you might’ve saved $50 bucks on a cheaper flight but you lose it eating three meals at Chili’s Too and tipping the shoeshiner while you wait to find out how long you’ll have to wait for them to tell you when you might get an update on your flight.

Go for a late night stroll through the South Side.

I believe it was Chief Keef who once said, “I’m South Side I’ll pop out, O-Block bring them glocks out, 300 bring them chops out, we shoot up your block now.”

O-Block is a notorious stretch of the South Side, known for being the most dangerous place in the city. If you find yourself there, do something that makes you look really crazy so no one messes with you. Punch yourself in the nose a couple times or bite the head off a pigeon or something. Let them know you’re psychotic and then request the nearest Uber. You don’t want to be around once the glocks come out and the popping out commences.

Go up in the Sears Tower.

Unless you like waiting in lines, a Google search for photos from the Sears Tower is the best way to take in the city’s highest view. The wait is often well over an hour and that is time you can spend doing something else, like not waiting in a line that’s well over an hour. The Signature Room on the 95th Floor of the John Hancock Building is the place to go if you want a good view without the crowd.

The Game

… is going to be a blowout. Kentucky should cruise past UCLA and set up a fun evening in Chicago. We’ll have more on the activities and the Bruins throughout the week.

Beat UCLA.

Article written by Drew Franklin

I can recite every line from Forrest Gump, blindfolded. Follow me on Twitter: @DrewFranklinKSR

9 Comments for KSR Travel Guide: Chicago

  1. hersheyisabear
    9:52 pm December 15, 2014 Permalink

    Watch out for bums trying to bum 45 bucks off of you for a bus tickets to philly because their “old lady”just had a baby. They will then proceed wit showing you a crumbled up baby picture of the opposite race of their own. Just a heads up. Go Cats!

  2. Catsby80
    10:28 pm December 15, 2014 Permalink

    Do: go to Giordanos pizza on Rush street. Best pizza in Chicago but be prepared to wait. If you go on Saturday night, there will easily be an hour wait. It’s worth it. You’re welcome.

    • UK Big Board Update
      11:11 pm December 15, 2014 Permalink

      Agreed. Good call.

      Ditka’s also has one of the best bone-in pork chops I’ve ever had.

  3. belgium
    10:38 pm December 15, 2014 Permalink

    There is a very nice Christmas Market (Christkindlmarkt for the Germans out there) where one can eat some very tasty food, drink very tasty mulled wine, and generally have a good time people watching. It is on Daley plaza.

  4. CatsfaninFL
    7:38 am December 16, 2014 Permalink

    Disagree on the Sears/Willis Tower comment… if you go early, the wait is negligible. The glass overhangs are pretty cool to go out on and something you can’t do at just any tall building.

  5. dano
    8:38 am December 16, 2014 Permalink

    Do NOT take a cab to Chinatown unless you arrange for a return ride in advance. Go to Kingston Mines if you like blues. Completely disagree on O’hare. I fly there, have never been late, and don’t have to walk through the cesspool that is Midway.

  6. JandPsDad
    9:11 am December 16, 2014 Permalink

    Living in Chicagoland I’d have to agree with most. You need to try a Chicago-style dog from a legit vendor (not at the UC) – they are really good!!! Visitors need to stroll the “Miracle Mile” (Michigan Avenue north of the river) in the evening – it is magical this time of year! Oh, and this one last thing, have PLENTY of room on your credit card…

    • UK Big Board Update
      12:15 pm December 16, 2014 Permalink

      Miracle Mile is in LA, Magnificent Mile aka ‘Mag Mile’, is in Chicago. I agree, though, it is beautiful this time of year.

  7. kyblue96
    4:54 pm December 16, 2014 Permalink

    I’m advising you to skip the deep dish pizza and go to Portillo’s (Ontario/Clark). Get yourself an Italian Beef with hot peppers, cheese, and tell them to dip that mothertrucker. This is far more delicious and Chicago than that pizza.