Oprah — and Other Adventures in Chicago!

For 25 years, Oprah Winfrey has been our teacher, guidance counselor and cheerleader. In fact, she was – in so many ways – the inspiration for StyleSubstanceSoul.com.  So, when we were invited to be in the audience of a taping of her show last week, we dropped everything, booked plane tickets and headed to Chicago.  It was one of the most amazing experiences of our lives, and the actual show airs today. Set your DVR because you just won’t believe it!!

Although nothing can top that day, we did pack in a lot of other great sightseeing, shopping and eating while we were in the Windy City.  Amy had to work the whole time except for our day at Oprah, so Susan and I made sure we did enough for three people.  Here’s a little travelogue you might want to follow if you have a chance to enjoy a long weekend in Chicago.  We guarantee it will make you fall in love with the city just like we did.

We landed in Chicago around 12:30, and after quickly checking in at the boutique-y Raffaello Hotel which was recommended by one of our most-trusted traveling friends, we were on the 2:00 Architecture River Cruise.  Everyone told us this was a must-do, and they were so right. Sponsored by the Chicago Architecture Foundation, the fascinating hour and a half boat tour on Chicago’s First Lady was led by a volunteer docent with an encyclopedic knowledge of the city’s buildings and bridges.  It gave us a whole new perspective and appreciation for the spectacular skyline.

We headed off for an early dinner at Girl & the Goat, the new restaurant from Top Chef winner Stephanie Izard.  The atmosphere is welcoming and rustic, and the food farm-fresh and innovative.  We ordered a handful of small plates, including sauteed skate with grilled calamari, chickpeas, grilled radicchio and tomato aioli (that’s all one dish!), pork liver mousseline with ham hock jus, apple mustarda and crumpets, and the most flavorful sauteed green beans with a fish sauce vinaigrette that would make it easy to get in our daily veggies.  We could barely speak to each other because we were so busy “ooh”-ing and “ah”-ing over each bite.

Taking it as a sign that Harpo Studios was just a couple of blocks away, we made our pilgrimage over there to scope out where we’d line up the next day and take pictures of each other in front of the famous logo.  Trust us, we weren’t the only ones doing that!

Because our stomachs and hearts were so full and we were really ready for a nap, we decided to take in Spoiler Alert: Everybody Dies at Second City. Seated at a first row table, we knew we’d stay awake.  The show was so funny, we laughed until we cried, and I wish I had pictures of Susan, who was dragged onstage for her (excellent) acting debut.

The next day was OPRAH.  We pledged, along with the rest of the audience, not to say anything about the show until it airs so set your DVR – it’s on today, and you have to see what happened.

Emotionally drained after our Oprah experience, all we could do was grab a pizza at the famous Lou Malnati’s. Yes, the Chicago-style deep dish pizza was delicious, but I’m a New Yorker and a firm believer that nothing beats a slice of New York pizza.

The next morning, after a too-excited-to-sleep night — despite the most comfortable hotel mattresses and pillows we’ve slept on in a long time — we embarked on Chicago Food Planet Food Tours much-touted Near North Food tour. It was so much fun and our guide, Nicky, was so warm and knowledgeable, we felt like we were being given an insider’s look at the city by one of our best friends. We tasted everything from pastrami Reuben sandwiches to spinach-stuffed pizza — yum! — but the most pleasant surprises were at The Spice House, where we were treated to the freshest cinnamon we’ve ever tasted, and Old Town Oil, where we mixed Strawberry and Tangerine Balsamic Vinegars with Garlic and Tuscan Herb EVOOs that were so smooth and tasty, we didn’t even miss the bread. We also met Evie Thompson, a woman of style, substance and soul from Washington, D.C., who took the photo of Old Town Oil and who we’re happy to call our new friend.

From there, it was on to the Sears, uh, Willis Tower. After eating so much, we should’ve just walked to the 103rd floor Skydeck but, instead, opted for the elevator, which zoomed us up in there in 60 seconds. We tiptoed on to the Ledge — a glass, enclosed balcony extending four feet out and over 1,300 feet above Chicago. The view was breathtaking and, as we got braver, we sat down and then sprawled out on the glass.

We ended the day at Steppenwolf with the opening night performance of Detroit, a new play by Lisa D’Amour. The performances were pitch-perfect, especially Laurie Metcalf from Roseanne.

Our last day in Chicago, we had planned to spend the morning at the Renegade Craft Fair — we’ve been wanting to attend one forever, and were thrilled to see we were in the right city at the right time! — and the afternoon at the Art Institute of Chicago. Too tired to move, though, we ended up blowing off the Art Institute, figuring it would still be there next time. Instead, we took the advice of the Raffaello’s Jared Galbut and enjoyed brunch at Milk and Honey before spending the rest of the day — and the rest of our money — at the Renegade. We bought lots of goodies including gorgeous handmade journals from The Binding Bee and wooden birdhouses from Erick Erf.

We can’t wait to go back to Chicago, and hope you’ll share your favorite experiences there with us. Post a comment and you may win a copy of Jillian Michaels: Shred-It With Weights — something we definitely need after eating our way through the Windy City.

This post originally appeared on my former blog, StyleSubstanceSoul.