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A Chicago Getaway from Owensboro

by Christy Chaney
October 29, 2026
in Lifestyle
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Hot dogs, shopping, and a front row seat at Girl & the Goat

Photos and article by Christy Chaney

Taking a trip out of Owensboro does not always mean driving 2 hours to an airport. Sometimes it means driving 8 minutes. Around here, we like to say you can get just about anywhere in 8 minutes. On this trip, that included the beginning of a Chicago getaway this summer.

We flew Contour from Owensboro, stayed at The Peninsula, and made room for shopping, coffee, and an impressive amount of eating. It was the kind of trip that reminded me how much easier a getaway feels when it starts close to home.

Once we made it to the Windy City, our home base was The Peninsula, right by the Magnificent Mile, which follows North Michigan Avenue for 13 blocks, from the Chicago River to Oak Street. For a short visit, having shopping and coffee close to the hotel makes it easy to get out and explore.

First order of business: Food

One of the first things that had to happen was a hot dog from Portillo’s, followed by a chocolate cake shake. A milkshake with chocolate cake in it? Yes, please. And when I say chocolate cake, I mean they put an entire slice of their famous chocolate cake in a milkshake! I am not saying that was the entire reason I went to Chicago, but it certainly helped.

Of course, one cannot survive on hot dogs alone. That is why there is deep-dish pizza.

Chicago deep dish is a different experience from the pizza we usually order at home. It’s a sit-down-and-settle-in kind of meal, and the tomato sauce on top still feels a little wild to me. The other thing you need to know is that you are not getting this in 30 minutes or less. This pizza is 45 minutes from order to table, so take someone you have something in common with because that’s a long time to make conversation with a stranger! There are plenty of places to partake of this pizza: Lou Malnati’s is the chain to know, but Pequod’s, Giordano’s, and Gino’s East all throw down a very heavy pie.

Still, sometimes you need more than pizza and hot dogs on your trip. Gene and Georgetti took us back to 1941, when Gene Michelotti and Alfredo “Georgetti” Federighi opened it together. A quintessential Chicago steakhouse — including red leather seating and servers in black vests — this is the oldest steakhouse in the area and a favorite of old blue eyes himself, Frank Sinatra.

A little shopping and a little magic

Walking along Michigan Avenue, it’s easy to find a number of clothing stores. There was an amazing variety from high-end to small boutiques. What I was especially pleased to find was magic: the Harry Potter Shop at 676 North Michigan Avenue.

For the record, I am a Slytherin. Some of you are not surprised. I found plenty of things that could work for Halloween, or, in my case, an ordinary Tuesday. If Harry Potter is your thing, give yourself time to browse.

The Starbucks Reserve Roastery was another stop worth making. It is absolutely stunning, and it feels like Starbucks on steroids. You know, if Starbucks did steroids instead of shots of caffeine.

Starbucks describes the Chicago Roastery as its largest location in the world, at 35,000 square feet. The space includes a working coffee roaster, an experiential coffee bar, and a cocktail bar, but do not expect to order your usual coffee. This is a much more elevated experience.

My kind of courtside seats

My favorite stop of the trip was Girl & the Goat. Chef Stephanie Izard has been someone I have enjoyed watching on television for years, so eating at her restaurant was already something I was excited about.

We sat at the chef’s table, with a view into the kitchen. The menu was chosen for us, and every single bite was delicious.

Being able to watch the chefs prepare our food was like having courtside seats. Some of y’all may be dreaming about sitting courtside at a Bulls game. I was dreaming about a front-row seat in Stephanie Izard’s kitchen.

Home again

Eventually, we headed back to the airport and flew home to Owensboro. Our car was waiting, and 8 minutes later, we were home. The convenience was part of the pleasure: a trip full of big-city experiences that began and ended right here.

There are so many things to do in Chicago that you cannot possibly get to them all in a weekend. So next trip, I hope to take a cruise down the Chicago River where a guide shows you all the architectural wonders. I am planning to jump into sprinkles at the Ice Cream Museum and maybe even take a turn on the Ferris Wheel at Navy Pier. There’s so much more to do in a town that is literally a hop, skip, and a flight away.

The next time you need a change of scenery, Chicago deserves a look. Pick a few places you really want to visit, leave time for a good meal, and remember that your getaway can start just down the road. OL

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