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!

Sarah’s Perfect Day in Chicago

As a resident of Chicagoland who left and returned, I have a renewed appreciation for all the wonderful things the city offers. My favorite day is a sunny Saturday. I would start off my morning with a Metra train ride downtown to Millennium Park. The park is beautiful with many attractions.

The Bean

While in the park, stop and see the skyline (and yourself) reflected in what we affectionately call ‘The Bean.’ The real name is “Cloud Gate” and it was made by a British artist Anish Kapoor. Inspired by liquid mercury, the sculpture is among the largest of its kind in the world, measuring 66-feet long by 33-feet high.

The Art Institute of Chicago

After you’ve seen ‘The Bean’, I recommend moving on to The Art Institute of Chicago. Filled with art students, residents and tourists alike, it is a stunning collection of some of the world’s finest artwork. Currently at the museum is Van Gogh’s The Bedroom exhibit. This is the first time that all three versions of The Bedroom are together in North America. The paintings themselves are featured along with a technologically advanced study of their making and an insightful analysis of their meaning to VanGogh. This exhibit makes for a ‘must see.’ Other pieces you have to see while you’re there include: A Sunday Afternoon on the Island of La Grand Jatte by Georges Seurat. Nighthawks by Edward Hopper, Paris Street; Rainy Day by Gustave Caillebotte and The Old Guitarist by Pablo Picasso.

The Signature Lounge

After all of that walking and fresh air, you’ll need some time to kick back and relax. If you’re up for more sightseeing, I recommend heading to the John Hancock building, now known as 360 Chicago. The observation deck is the perfect place to see unbeatable views. If you’re feeling a little less touristy, head over to the signature lounge to relax, enjoy a drink or appetizer and soak up sky high scenery. It’s an excellent destination for a bloody Mary or to watch the sunset.

RL Restaurant

If you’re feeling the need to really people watch and experience a true lux environment, have lunch at RL Restaurant. While the food is a bit pricey, the atmosphere, billed as ‘the vision and décor of Ralph Lauren and modern city-club cuisine in the heart of Chicago and artwork can’t be beat.

Hot Tix

Now on to nightlife! From here, there is nothing better than catching some of Chicago’s theatre. Head to Hot Tix on 163 E. Pearson St. and sign up for a half-price show. Whether you are into comedy, performance art, musicals or opera, there is something for everyone. Hot Tix is run by the league of Chicago Theatres, which means you get great deals and help fund the Chicago theatre community.

Jackie’s Perfect Day in Chicago

Chicago Lakefront/Museum Campus Tour

If you’re tired of walking, but still want to learn about and see all the great sites Chicago has to offer, I highly recommend doing it via a Segway tour. Segway tours are the best way to see a lot in just a couple hours. Don’t worry if you’ve never ridden a Segway before! Prior to departing, everyone gets a thorough training on how to drive them and it’s surprisingly easy and super fun. Try the Chicago Lakefront/Museum Campus tour, which departs from Millennium Park. You’ll cruise along the beautiful floral pathways of Grant Park, have some great photo ops by Buckingham Fountain, plus you’ll see some amazing views of the city skyline from the Museum Campus. Even though it looks a little dorky, I promise you’ll have so much fun riding along you won’t mind a bit!

Chicago Cultural Center

Want to experience a little Chicago history but strapped for cash and/or time? Check out the Chicago Cultural Center located at 78 E. Washington Street, just across from Millennium Park.  This stunning landmark building has free exhibits and the world’s largest stained glass Tiffany dome! It’s truly a delight to the eyes.

Rosebud on Rush

If you’re hungry for large portions of authentic Italian cuisine, look no further than Rosebud on Rush. If the weather cooperates, grab a seat on the patio and enjoy some good people watching. The gravy (red sauce) and meatballs are to die for. Another favorite is the brick chicken, which is big enough to split. Make a reservation to avoid a wait!

Siena Tavern

Siena Tavern (51 W. Kinzie St.) is another place I highly recommend and is located in the bustling River North area.  Whether you’re looking for a fine dining experience or just want to sip on some delicious craft cocktails pre- or post-dinner, the lively ambiance of Siena Tavern won’t let you down. FYI, you’ll definitely need a reservation for a group dinner.


Kyle’s Perfect Day in Chicago

Divvy Bike

Start the day in Lincoln Park. The best way to get there from Downtown is via bus, Lyft (or Uber), or if you want some exercise grab a Divvy bike (which can be rented for a half hour at a time at various locations throughout the city) and ride north along the lakefront path.

Orange Restuarant

Grab brunch at Orange Restaurant, a popular spot featuring coffee infused with orange peels. Also order, fresh squeezed juice, a wide range of entrees and its most well known and unique creation, fruit sushi rolls known as frushi.

R.J. Grunts

When you get hungry, head over to R.J. Grunts for a burger. This quirky restaurant is a staple of the neighborhood and has great burgers, sandwiches and onion rings.

If you are ready to keep the day going, head over to the Bucktown/Wicker Park neighborhood. Work off some of those calories by taking a walk on The 606, an elevated bike/walking path that runs for almost 3 miles. Exit the path at Damen Ave., head south and you will pass by numerous bars, restaurants and boutique shops. Take your time and explore.

Big Star

Once you are ready for dinner, head to Big Star for some of the best tacos in the city. There usually is a bit of a wait and it is cash only, but the food and lively atmosphere is worth it.

The Violet Hour

End the night across the street at The Violet Hour. It is a speakeasy-style cocktail bar offering pre-Prohibition libations. There’s no sign outside, just a hidden door in a big mural on the side of a building, marked by a single light bulb. You will know you are in the right place when you see the line. In the spirit of full disclosure, I have never been to The Violet Hour but have heard great things.

Wrap up your night and head back to your hotel at your leisure. Hope you enjoy a great day in Chicago.

Angela’s Perfect Day in Chicago

Second City Comedy Club

Second City is hands down the best comedy club in the Chicago area. If you didn’t already know, Second City used to be home to big names like Steve Carrell and Tina Fey, so the cast is always extremely talented and never disappoints.

There are many different shows to chooses from, including sketch, improv and even the “Best of Second City.” Personally, I favor the sketch shows because they are cleverly written, whereas the improv shows completely rely on the audience’s responses, which may or may not be funny.

As far as the atmosphere goes, Second City has an intimate comedy club feel. It is a bit of a tight squeeze, but it’s all part of the experience. Treat yourself to a drink and be prepared to cry from laughing.


Portillo’s is a Chicago staple. If you’re looking for Chicago-style food, but are looking to eat fast,  Portillo’s is the place for you. Portillo’s is not only known for its food, it’s also known for its diner ambiance that takes you back to the 50’s. You can even see your food being made!

Disclaimer: There’s only one Portillo’s in the area, so make sure to avoid peak lunch/dinner hours.

Top Things to Try

1)If you’re looking for a good Chicago-style hot dog, be sure to try the Portillo’s jumbo dog with everything on it, but no ketchup! Make sure to get cheese fries to go with it. Don’t worry- this cheese doesn’t taste fake. In fact, you’ll want to put it on everything.

2)I’m usually not a big fan of ordering salads when going out to eat, but the chopped salad is an exception. This salad is the perfect ratio of chicken, bacon, tomatoes, gorgonzola cheese, green onion and red cabbage, so you won’t be picking out just the bacon.

3)If you’re looking for something sweet to top of your meal, try Portillo’s famous chocolate cake. It’s delicious, but it’s very rich, so split it with someone else or else you’ll face chocolate overload.

Shedd Aquarium

If I had to choose one tourist attraction to visit in Chicago, it would be the Shedd Aquarium. After all, its claim to fame is being one of the largest indoor aquariums in the world.

If you’re looking to simply visit the exhibits included in general admission, you need about 2 to 3 hours to see everything. My favorite exhibits are the beluga whale tank and the Wild Reef. Often times, I forget about the  Wild Reef until the very end because it is located in the basement of the Shedd Aquarium and it requires taking a specific elevator, so make sure not to forget! I love the Wild Reef because it gives me a diver’s-eye view of sharks and fish – a view I would not want to experience otherwise because diving terrifies me.

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