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Tasting my way through Chicago’s Gold Coast

I recently tasted and snacked and nibbled  my way through Chicago.  Not hard to do.  Plenty of great restaurants in the Windy City.

This was different.  A friend and I took a Tastebud Tours, a culinary adventure that took us to a variety of eateries in the Gold Coast area, exposing us to hot spots, history and some darn good chow down.

The three hour tour ran over lunchtime, led by a young foodie/graphic artist who once fancied herself a chef, until she worked in a restaurant.  She hated it.  Found she loves taking folks on tours instead.

We started at Pizano’s Pizza & Pasta on North State Street, known for its deep-dish pizza, invented in Chicago and a favorite of mine. We ate in the celebrity room, known for hosting folks like Barack Obama and Oprah.  It had that back room hideaway feel. I could imagine hot shots scooting in the back door to avoid persistent photographers.

We popped into Sarah’s on Oak Street to learn about his young chef, Sarah Levy, from a foodie family in Chicago, who whips up fabulous chocolates and wedding cakes for glitterati.  She brags that Martha Stewart is a buddy and has endorsed her efforts.

The brownie there was divine.  Will go back for another one. The rich creamy center slid down my throat, but  stuck in my mind. I understand it is Sarah’s Mom’s recipe.

We learned that the brownie was invented in Chicago by the chef in the well-known Palmer (as in Hotel) family. Mrs. Palmer wanted something special and chocolaty for a picnic.

From there we toured the grand tearoom of the Drake Hotel, fancy and fussy.  It is a great walk-through if you haven’t been there. The Drake has been around since the late 1930s, anchoring the end of Michigan Ave. on Lake Michigan hosting celebrities including Princess Diana. Scads of history.

At one time, this part of Chicago was so undeveloped that guests could hit golf balls off the roof.


What a contrast it was to the stop at Downtown Dogs on Rush Street for the famous Chicago hot dog.  The ingredients are carefully dictated and for sure, no ketchup.  If you put ketchup on your Chicago hot dog, you’ll be laughed out of town.  The hot dog was invented in the Depression, providing a whole meal—cheap meat, veggies and bread all in one item.

We also walked by the Saint James Cathedral to see the scorch marks on the brick from the Chicago fire and peeked into the old Water Tower to see the big pumps. I was intrigued with this sculpture in front of the church.  This is the third sculpture in a series of four.  The artist Mary Seyfarth calls it “Pentecostal Foot” and says the idea is “A naked foot walking out of a boot print….out of the past and into the future.”

I didn’t particularly enjoy the Heaven on Seven, an ode to New Orleans, because I don’t like spicy food, but my travel mates gobbled down the Gumbo and Jambalaya.  I fell in love with the visual effect of the wall of hot sauces that formed the décor.

Two more stops—couldn’t have been more different.  Billy Goat Tavern located under Michigan Avenue and loaded with history.  Named for a goat who was a pet of the original owner and went everywhere with him.   I’ve had better hamburgers but love the history and gritty atmosphere.


The last stop was trendy and cool.  The Purple Pig.  Award winner.   Gorgeous wine glasses and communal seating. Creative menu.  I was told the wait could be more than an hour with no reservations taken.  Innovative menu and hip atmosphere makes it a DesignDestination in my book.

My friend and I ended our tour with our own adventure. We headed to the top of the Hancock Building to the lounge at the Signature Room for a glass of wine and the fabulous view. The lounge is a great spot to see the lake, coastline and sprawling city in a relaxed way.   Perfect stop off point before hopping the Amtrak for the long ride home.

A bit of advice: if you are going to be in Chicago for a couple of days and decide to take this tour, do it early in your visit.  Tastebud Tours give you discount cards for a variety of foodie spots both on and off the tour.  Make sure you have some time to enjoy them.

Do you have recommendations for special Chicago eateries?  Hope you’ll leave them in the comment section for all to enjoy.  Thank you.



Post Author
Susan J. Smith
Susan's career includes writing for newspapers, lots of community work and a wonderful family life. Now she is enjoying traveling, photography and writing for DesignDestinations and Grand Rapids Magazine. She welcomes you on her journey and appreciates your comments.


  1. posted by
    Apr 23, 2011 Reply

    Nice report You know me I am a sucker for all things Chicago! You really should try Quarttinos. Great spot on Ontario. Thanks again for a quick trip home! Chef Perkey

  2. posted by
    Apr 23, 2011 Reply

    Thanks for your nice comment. Much appreciated. I will put Quarttinos on my list for another trip to Chicago. With a recommendation from you it must be good.

  3. posted by
    Apr 23, 2011 Reply

    We (Visbeen Associates, Inc.) are in the midst of opening an office in the Historic Motor Row area of S. Michigan Ave. Love having more info on where to eat in Chicago. You can see images of the loft space on Visbeen Associates Blog. More to come, Thanks.

  4. posted by
    Apr 23, 2011 Reply

    For breakfast food, try Nellie’s on W. Division in Humboldt Park. Coconut oatmeal is divine! Even those who say they don’t like coconut or oatmeal say they love it. Lots of plantains too.

  5. posted by
    Apr 25, 2011 Reply

    The breakfast sounds yummy. Thanks for the tip.

  6. posted by
    Apr 25, 2011 Reply

    A stop at The Bongo Room for breakfast is a must! Two locations – Milwaukee and Wabash. Be prepared to eat!

  7. posted by
    Joyce Hecht
    Apr 25, 2011 Reply

    More lore regarding the Billy Goat Tavern: The owner took his pet goat to a Cubs game. People sitting near the two some compained about the smell, so the owner and the goat were thrown out of the ball park ,but before departing, the owner put a curse on the Cubs saying that they would never win another world series game…and they haven’t.

  8. posted by
    Ann Stevenson
    Apr 28, 2011 Reply

    Chicago is such a wonderful town, I’m adding the tour and restaurants to my must do list.

  9. posted by
    Margaret Cheff
    Apr 30, 2011 Reply

    Susan, I loved the photos of the Chicago skyline…OK…I know the article is supposed to be MORE about the eateries, not the skyline. So I’ll throw in my two cents about one of my “faves” in Chicago, and I found out about it from YOU, my foodie friend. How about “North Pond”? Absolutely the BEST (and local) food…and of course, the Chicago skyline seen from across the pond is wonderful.

  10. posted by
    May 2, 2011 Reply

    Thanks, Margaret,
    The view was wonderful that day. Clear. Great color.

    I agree about North Pond. Here’s the Link to my post on this restaurant on the North Pond. It was originally a warming shed for the skating rink when the pond froze over.
    Great atmosphere and food.

    We’ve celebrated several birthdays and a graduation there and enjoyed quiet evenings with friends. Never been disappointed.

    Thanks for mentioning.

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