Head to the Windy City, Chi-Town, the Best in the Midwest – however you refer to Chicago, it’s one of the greatest cities in the nation thanks to its unique mix of midwestern charm and big city vibes. Between the picturesque cityscapes, cultural attractions, local food, and weekend events, there’s no place quite like Chicago. Every year thousands pound the pavement for the Humana Rock ‘n’ Roll Chicago Half Marathon, the Humana Rock ‘n’ Roll Chicago 10K, and Humana Rock ‘n’ Roll Chicago 5K.

Participants get to run past some of the most popular spots in the city, including the famed Magnificent Mile, Willis Tower, Soldier Field, Chicago Theater, and all through the Loop. It’s a great way to see the city at a glance, but if you want to get a true Chicago experience, you’ll have to carefully plan your 48 hours. We’re here to help.


It’s the first day of the Health & Fitness Expo, which means you can load up on swag and race day necessities before you take on the city. The Expo is at McCormick Place, which happens to be the largest convention center in North America, so expect to find something special to commemorate your race and Chicago experience among its rows of vendors and sponsors.

Pet a Penguin at Shedd Aquarium

From McCormick Place, make your way south, following the waterviews, and stop at the famed Shedd Aquarium. Save time and buy your tickets online so that you can make your way through as many exhibits as possible. While the aquarium is incredible on its own, you can also sign up for their regularly scheduled special experiences, such as feeding a shark, petting a penguin, or getting up close and personal with a beluga whale.

Walk the Ledge at Willis Tower

What was once known as Sears Tower, this skyscraper gives visitors some of the best views of the city. For those who aren’t afraid of heights, head up 103 floors and hang out on the glass-bottomed balcony to look down on the city below. Don’t worry, you don’t have to climb the stairs – an elevator will whisk you to the top.

Fun fact: When the weather cooperates, you can see four states in one day: Illinois, Indiana, Wisconsin, and of course, Michigan.

Stop for Lunch at Luke’s Italian Beef

Chicago is well-known for its culinary offerings, and before or after your time at Willis Tower, make sure you stop by Luke’s for their famed Italian Beef Sandwich. For less than five bucks, you can get one of the city’s delicacies in a spot that’s no frills, but focused on putting out good food. However, if you’re dying to try a true Chicago-style dog, you can’t beat the price here. For just $2 and change, you can indulge in another destination favorite with all the traditional toppings, including the signature electric green relish.

Laugh It off at The Second City

Tour the halls and performance spaces where many famous comedians got their start. The Second City is located in Chicago’s Old Town neighborhood and delivers hilarious improv night after night. Choose from different skits and make your reservations in advance because it’s a favorite among those visiting Chicago, especially during the summer season. Depending on where you sit and what show you sign up for, you just might find yourself as part of the act.


If you’re running the Humana Rock ‘n’ Roll Chicago 5K, today is your day. Starting bright and early at 7:30 AM, it could be the perfect warmup for those running the half marathon the next day.

The 5K starts and ends at the waterfront, overlooking Lake Michigan. Get your finisher medal, listen to live music, and enjoy an energizing start to your day. Whether you run solo, in a duo, or with a group of pals, you’re sure to enjoy the views and vibe of this electrifying event.

Giordano’s vs. Gino’s East

Deep-dish pizza is a big deal in Chicago. Visitors from around the country make it their top priority to sample more than one slice of this layered goodness. Out-of-towners have even been known to ship some home. No one complains much about the wait, because when it arrives at the table, everyone is silenced into a feeling of food-loving joy. But the real question remains: Are you Team Giordano’s or Team Gino’s East? Everyone has their vote of preference, but you can’t go wrong with getting your deep-dish fix at either spot. This is one battle people happily call a draw. After all, everyone comes out a winner when they finish a good meal.

Visit the Home of the 2016 MLB World Champions

The Cubs finally brought home a title in the 2016 season. They’d only been waiting 100+ years to take back the baseball crown, but who’s counting? Game 7 ended in dramatic fashion with the rain delay and extra innings. But eventually, the Chicago Cubs bested the Cleveland Indians to become World Series champs. Even if you don’t care much about baseball, you can’t deny the history of Wrigley Field. Walk through the dugout, visitor clubhouse, and press box of the historic stadium on a tour. It’s one of two MLB stadiums to still have a hand-operated scoreboard and cheap seats on rooftops. Afterwards, stop for a drink in the famed Wrigleyville neighborhood.

Take a Selfie at “The Bean”

No, it’s not officially called “The Bean,” but everyone knows this famed sculpture by its nickname more than its actual Cloud Gate name. It holds court in Millennium Park, in the Loop, next to the Art Institute and not too far from Navy Pier. Snap a selfie and stand in awe at one of the most photographed art pieces in America. No one can pass up a chance to pose with one of the city’s best-known landmarks. Its reflective surface makes for the perfect group mirror selfie or distorted skyline pics.

Appreciate the Architecture

There are art and architecture built into every corner of the city, but one of the best ways to view them is by boat. Take a cruise along the Chicago River as a guide points out some of the most famous architectural spots in the city, sharing where you might’ve seen them before and how they are linked to the city’s history.


Get a good night’s sleep on Saturday and you’ll feel energized and ready to run the half marathon or 10K on Sunday. There’s no experience quite like running a Rock ‘n’ Roll race in Chicago during the summertime. Just be sure your legs are ready.

Let the party vibe move you through the 13.1 miles to the finish line in Grant Park, where you’ll be greeted with your celebratory beer and well-deserved exclusive finisher medal.

The ultimate Chi Town run awaits. We’ll see you there!