8:00- Go for a Stroll on Chicago's lakefront trail
Once Chicago says ‘so long’ to its negative temperatures for the season, locals jump at the opportunity to get outside. Whether you are looking to get some exercise or just do some people watching, the Chicago Lakefront Trail should be your first destination. You can run, walk, rollerblade or even rent a Divvy Bike from locations around the city.
11:00- Brunch at Cindy’s Rooftop
Brunching has become any Chicagoan’s favorite activity and Cindy’s Rooftop has brought the activity to new level. Sitting on top of the Chicago Athletic Association, the restaurant offers jaw-dropping views of Millennium Park and Lake Michigan. The restaurant offers several platters large enough to share with 2-3 people, or if you are feeling ambitious, feel free to take on their delicious nutella banana pancakes all for yourself.
12:00- Check out the famous Millennium Park
After Soaking up the views at brunch, it’s time to start exploring Millennium Park for yourself. While the Cloud Gate sculpture (AKA the “bean”) might entice you for a quick snapchat, you’ll quickly learn why the locals stay far away from this attraction. The park takes up nearly 25 acres, which means there is plenty of other places to discover and explore.
1:00- Visit the Art Institute
When you are done moseying through the grassy park, peek into Chicago’s favorite museum, the Art Institute of Chicago. The museum is home to some of the world’s most renowned art, but if you are looking for something a little different, check out the museum’s new modern wing.
2:00- Test out a Chicago Style hot dog
No visit to Chicago is complete without an authentic Chicago style hot dog, so its a good thing local carts are located all throughout the park-- just remember, no ketchup!
3:00- Take a peek at Chicago’s “coast”
While some may scoff at the idea of Lake Michigan, be sure to avoid those thoughts while talking with any locals, as they are very protective about the body of water. Whether you decide to jump on an architectural boat tour through the city, test your balance by renting paddle boards at the popular North Avenue Beach or, get in some R&R at the more relaxed Ohio Street beach, make sure to give the lake scene a chance before judgement.
7:30- Bit into Deep Dish Pizza
There is a reason that Chicago is known for their pizza, and we promise if you’ve never tried deep dish before you will quickly understand what you’ve been missing. Try your hand at the cheesy goodness at Gino's East or Lou Malnati’s to experience the originals.
8:00- Get in a laugh at Second City
Chicago’s late night scene is one of the liveliest in the country, so what better way to start your night out than with some cocktails and laughs. Second City is an improv comedy club that hosts shows almost every night. The club is known for being the starting point for several comedians such as Bill Murray, Tina Fey and Steve Carell.
11:00- Stay out Late
A Big city means big nightlife and, Chicago won’t dis\appoint you. With some bars open till 5am, you’ll surely stay entertained all night long. Places like The Owl, Celeste and Kingston Mines keep going until the early hours if you are ready for that.