Get Your Heartbeat on in Chicago

Here at Springboard, we believe in making hearts beat with excitement, passion and hope. What better way to do it than exploring Chicago. Being a Chicagoland-based agency, we know a thing or two about Chicago and would like to share some insider tips with you.

Rob’s Perfect Day in Chicago

Wells Street

Start your day walking down my favorite street in Chicago, Wells Street.  Located between Division and North Avenue in the heart of the Old Town neighborhood, you’ll find many unique shops, coffee spots, and breakfast/brunch restaurants.  Make note of the names along the way as you might want to revisit for late afternoon cocktails or dinner. Wells Street is also host to many of Chicago’s famous comedy clubs such as Second City and Zanies.

Either for a hearty laugh or meal, you’ll find Wells Street offers a great slice of a Chicago neighborhood.  And speaking of great slices, there are countless pizza restaurants along the way, too.

North Avenue Beach

When you’re ready to move on, either walk or Divvy (there are several rental bike stations on Wells Street) to North Avenue Beach.  Here you can either watch some great beach volleyball games or just soak up the sand and sun.  Walk north or south along Chicago’s famous lakefront – either way, you can’t go wrong.

Chicago is a walking town!  Go south and you’ll run into the world famous Lincoln Park Zoo.  Free to the public, the zoo offers a full array from the animal kingdom framed between Chicago’s lakefront and skyline.  Go north and you’ll see Chicago’s most famous beach, Oak Street, and some very serious sun bathers. Keep going and you’ll soon be on the Magnificent Mile, where world-class shopping and eating await.

River Walk

If time permits, visit the new River Walk and check out the many fun bars and restaurants along the water.  You can also take the architectural tour which is a fantastic way to learn about Chicago’s history and the background of many of the buildings that make up the famous skyline.

Chicago is a heartbeat city, especially in the spring and summer!  You can spend countless hours walking and biking and taking in all the sites along the way.  And with the array of restaurants in town, you’ll need the exercise to balance all the great pizza, ribs, and other famous foods you’ll also take in.




Mike’s Perfect Day in Chicago


One of my favorite things to do in Chicago is to listen to live music. Combine great music with a beautiful lawn at arguable the best downtown park in the country at the Pritzker Pavilion at Millennium Park. Bring a blanket or lawn chair, bottle of wine, some cheese and crackers and you’ve got a wonderful night under the stars. See who’s playing here and don’t worry if you’ve never heard of them, just go.

Get everything you need (except the blanket or lawn chair) at Pastoral Cheese.

Boat Tour

Another favorite is the architectural boat tour. Go on the one sponsored by the Chicago Architectural Foundation.

Take the twilight tour through downtown Chicago and enjoy the scenery along with the expert commentary about the history of our fantastic buildings.

Wrigley Field

Unfortunately, the Cubs aren’t in town but that doesn’t stop the party. The Wrigley Field Tours are a great way to visit Wrigley. After the tour, there’s no shortage of watering holes surrounding the park – pick any they’re great.  If you’re feeling inspired, step into a batting cage at Sluggers or chill on a rooftop at Casey Moran’s.


A touristy must do – Grab a “cheezborger” at the original Billy Goat Tavern under Michigan Avenue. Watch the old Saturday Night Live skit that made them famous before you go. My tip, get a double or triple – the buns are huge and burgers are thin. A Schlitz on tap makes it a perfect meal.

Ethnic food paradise – Chicago has some of the most diverse neighborhoods of any large city and the ethnic food will make you feel like you’re in the old country. A couple of my personal favorites:

For Italian food that’s better than your “Nonna” made in an atmosphere that will remind you of an Italian family’s dining room, skip “Little Italy” and go to the “The Heart of Italy” neighborhood. My favorite restaurant is Bacchanalia. Two words of warning: you won’t be able to stop eating and they don’t take credit cards – so bring a big appetite and a check or cash.

For Greek food that’s always fun, go to Rodity’s in “Greek Town.” If you haven’t had it, get the Saganaki (flaming cheese). It’s great, but don’t get a gyro – I love the Yiouvetsi pasta or the Osso Buco. Yum.

Cori’s Perfect Day in Chicago

Ravinia Festival

Take the Metra train out to Ravinia to see live music under the stars. Ravinia is a historic picnic-friendly outdoor concert venue hosting symphony, jazz, folk, rock, opera and more. It’s where I spend most of my “spare” time from June into September.

Millennium Park’s Hidden Garden

Everyone knows about Millennium Park, but it’s what lies beyond the park that makes it a hidden gem. The Lurie Garden is an understated natural beauty that serves as the perfect environment for reading a book or having a summertime picnic. It also makes a great backdrop for photos.

Often times there’ll be live music at Jay Pritzker Pavilion in Millennium Park too. It’s all about the music for me!

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