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The Ultimate Chicago Weekend

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Chicago Theater

When my parents announced that they were coming to visit for the first time in three years I made it my mission to show them such a wonderful time that they wouldn’t let so much time pass before their next visit. asked me to create the Ultimate Chicago Guide, so after much consideration and planning I created an itinerary for the Ultimate Chicago Weekend! Let’s go!


Restoration Hardware

Brunch at the 3 Arts Club Cafe: This restaurant is located in the courtyard of the most insanely gorgeous Restoration Hardware. It seemed like the perfect place to toast to welcome my parents to the city.

Scramble at 3 Arts Club Cafe

I highly recommend ordering the scrambled eggs, truffle grilled cheese, and the burger.

Original Playboy Mansion

Exploring the Gold Coast: Next up we walked off brunch with a stroll through the Gold Coast neighborhood. We stopped by the original Playboy Mansion (1340 N. State Street), and then walked up Astor Street admiring the mansions.

The Chicago History Museum: I love this museum. It’s size is manageable and you can see everything in just a couple of hours. I love the dioramas showing Chicago’s history, especially the one of the White City from the World’s Fair. Then we went to the Secret Lives of Objects exhibit which brings together a series of stand alone objects with fascinating stories that don’t fit into any other exhibits. The descriptions of the objects are cleverly written from the object’s point of view, giving the sometimes somber histories a more light hearted tone. I learned so much from this exhibit, for example – did you know that there was a major flood in Chicago in 1992?! If you are in Chicago I recommend visiting the museum, and walking through the Secret Lives of Objects.

The Second City: This comedy club is a Chicago institution, and the place where many start of Saturday Night Live got their start. My parents were on the fence about going, but haven’t stopped talking about how much they loved it. The Second City runs multiple shows at different times throughout the day. We went to see The Best Of Second City show at 4pm since we wanted to go before dinner, but there are evening shows too.


Dinner at Formento’s: My Mom is an avid reader of this site, and when she read my review of Formento’s she told me that she wanted to go there the next time she visited. I love Formento’s classic Italian food, especially their pastas, and their chocolate hazelnut cake is one of my favorite desserts.


Bar Siena

Brunch at Bar Siena: This might be the Chicago restaurant with the most man-friendly brunch menu, and the space walks the line between elegant and industrial. You can choose between egg dishes, pizzas, and pasta making this an ideal spot for people who prefer lunch over brunch. I had the avocado toast, while my parents both orders the short rib hash. My mother said it was one of the best brunches she had ever had.

Skating in Millenium Park

Ice Skating: Chicago has two centrally located ice rinks. The newest is the ice ribbon at the large new Maggie Daley Park. The ribbon is a long thin link with gentle curves. It’s a more fun alternative to the traditional rinks. In the center you will find the park’s rock climbing wall. The park itself is a paradise for kids. I had never seen anything like it before.

We went to the Millennium Park rink, right in front of Cloud’s Gate, or “the Bean” as locals call it. This is a traditional round rink. My Mom couldn’t believe how affordable this was! She says skating in New York city is $25 plus $12 to rent skates. In Chicago, skating is free if you bring your own skates, and skate rental is $12. Both Millennium Park rink and the skating ribbon at the Maggie Daley Park open in Mid-November.

Macy's Window

Seeing the Christmas Windows at Macy’s: Next we went to see the Christmas windows at Macy’s. This was my favorite window, even though the Chicago skyscrapers and the Macy’s parade don’t really make sense together.


Latinicity; Chicago’s newest food market is Latinicity in Block 37. The space is filled with individual stands serving everything form stir fry to burgers, and it boasts a total of 99 different menu items. It’s the perfect place for a mid-day snack.


Dinner at Bavette’s Bar and Boeuf: When people ask me which Chicago restaurant is my favorite, I reply “Bavette’s” without any hesitation. The usual response is a nod of agreement that Bavettes is certainly one of the very best restaurants in Chicago. My parents loved everything about it. They thought the corkage fee of sharing a glass of wine with another table was charming. They gobbled up the Wedge Salad with bits of thick cut bacon and blue cheese, and ate every bit of their entrees. My mother had the short rib stroganoff, one of my personal favorites, it’s a rich dish comprised of fresh pasta in a cream sauce topped with cremini mushrooms and chunks of tender short rib. Dad had the lamb chops and got every last little it of meat off the bones, Charles had the Chicago Cut Steak and I had the petite filet. If you are looking for an extra special place for a meal, Bavette’s is sure to please. Just make a point to save room for the chocolate cream pie.

Other Chicago Activities that we loved from other trips:
The Architectural Boat Tour: This is the best way to learn about Chicago’s stunning architecture. The informative tour takes you along the Chicago River and through the heart of the city.

Drinks at the Signature Room: If you want the best view in Chicago, I recommend the Hancock Tower since it’s one of the city’s tallest buildings, and you can also admire the Sear’s Tower (now the Willis Tower). The drinks are a little expensive, but it’s still cheaper than buying tickets to go to the top of the Willis.

Brunch at Southport Grocery: It’s been many years, but my mother still remembers how much she loved their Bread Pudding Pancakes.

Catching a game a Wrigley: The home of the Cubs is one of the last great classic ballparks in America. Just don’t put any ketchup on your hotdog there.

See more of Chicago here.

Did I miss any of your favorite places to visit in Chicago? Let me know your thoughts in the comments!

This post is in collaboration with The opinions expressed are my own.

Kelly in the City

Tuesday 2nd of February 2016

This looks like SO MUCH FUN! Definitely need to try these spots. :)


Thursday 28th of January 2016

Soo fun! I haven't been to so many of these places, I need to put them on my list! :)

Lauren Nolan

Thursday 28th of January 2016

Omg, Restoration Hardware AND Bar Siena brunch in ONE WEEKEND?! It sounds like my dream :) xo, Lauren |

Jenn Lake

Wednesday 27th of January 2016

Again, I must re-iterate how awesome of guide this is! It's the perfect itinerary for seeing the city! Thank you for sharing!

Heidi D.

Tuesday 8th of December 2015

This is such a cute idea! I'll have to try some of these next time my parents visit!

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