We have a casual date night idea on tap, and this guide gives us a good starting point to come out this way and explore the neighborhood. For our first stop, we’re going to a place that just exudes Chicago. When you walk in you get a dive-y bar feel, but it’s a bar with a kitchen run by your Italian grandma. There are no big frills, but it’s big on food, and you’ll have a chance to try all the classics. I’m talking chicken picante, tortellini, lemon chicken and potatoes, or just your classic spaghetti and meatballs with red sauce.
Here are some other notes.
– The restaurant is a few blocks north of the main strip in a residential part of the neighborhood.
– Menus are on big chalkboards throughout the diner
– Cash only and they don’t take reservations
After dinner, you can walk back towards the main corridor in Little Italy and stop by the famous Mario’s Lemonade stand for dessert. The DiPaolo family has has been serving Italian lemonade in the neighborhood since 1954, and there are no signs of them stopping. It’s been a Chicago institution since and for a little over $1 a piece, you can indulge on a refreshing frozen treat.
Lines can get long on a hot summer night, but they get people served pretty fast so don’t get too discouraged if you see a line snaking down the block. They are open every day during the summer (usually around May 1 to September) from 10-12am every day. 
As an alternative to date night, we’re going to start our neighborhood adventure with a picnic in the park. We’re starting the day getting our picnic provisions at this old school Italian grocer that also has a deli inside where you can get some tasty sub sandwiches for around $5 a piece. This isn’t like a Subway where your cheese comes in triangle form, but this is the type of place where your sandwich will come layered with fresh mozzarella and basil.
Since this is also a full fledged grocer, you can also put together a deluxe picnic basket of sausages, coppola, cheese and wine.
After you have your sandwiches and picnic supplies ready, then walk a few blocks to Arrigo Park, which is tucked away in Little Italy’s residential neighborhood and named after Victor Arrigo, an Italian-American who served as an advocate of the community in the 60’s.
There’s a huge plot of green space to set up shop, but on the East side of the park is an Instagram-worthy spot with the Willis tower peaking over the park’s tree line.
