Take a walk to Millennium Park to see a fantastic view of the Chicago skyline and iconic Chicago landmarks like Cloud Gate (aka The Bean) and the Buckingham Fountain where Jenn and Dan got engaged!
The Lincoln Park Zoo is an excellent place to spend a summer weekend afternoon! The zoo is one of the oldest in the nation (fourth oldest, to be exact!), featuring indoor and outdoor exhibits, many paths to walk along, and a carousel that you just can’t miss — and entry is free! Jenn and Dan had one of their very first dates at the zoo during ZooLights, an evening event during the holiday season.
The Lakefront Trail spans 19 miles, beginning at the southern end of the South Shore Cultural Center on Chicago’s south side and ending at Osterman Beach in Chicago’s Edgewater neighborhood. The trail follows the western shore of Lake Michigan and is the perfect place to spend a summer day, whether you’re walking, running, biking, or taking a pit stop at one of the many beaches (Jenn and Dan recommend visiting Oak Street Beach and North Avenue Beach)! Jenn and Dan walked along the trail on one of their many lakefront walks before making their way to the Buckingham Fountain, where Dan proposed!
The Chicago Riverwalk runs 1.25 miles along the Chicago River, boasting numerous restaurants and bars, and perfect for people watching and relaxing. It’s such a major Chicago attraction, it’s hard to believe it’s only been around since 2015! If you swing by, Dan and Jenn suggest stopping at City Winery or Tiny Tapp for drinks and Sweet Home Gelato for — you guessed it — Gelato!
A cruise along the Chicago River for an architecture tour is one of the most popular summer attractions! It’s a fantastic way to see some of Chicago’s most iconic buildings and learn some history too! While there are many great tour companies to choose from, Jenn and Dan recommend checking out Chicago’s First Lady.
If you’re looking for the best deep dish pizza in town, look no further than Lou Malnati’s! Although there are several locations around the city, the North State Street location was Jenn’s go-to when she lived one block away. Jenn and Dan are frequent patrons and are proud to order a large deep dish 100% of the time, Dan’s half predictably covered in pepperoni and jalapeños while Jenn varies her topping selections.
If you’re looking for upscale, classic Italian fare, check out Siena Tavern! It’s located in the heart of Chicago’s River North neighborhood and has everything you’re looking for in an Italian restaurant: excellent pizza, pasta, and cocktails. Plus, it’s where Jenn and Dan had their very first date as well as celebrated with dinner on the night of their engagement — at the same table and all! Siena Tavern also has one of the best desserts in town: a chocolate gelato cake that tastes even more amazing than it sounds!
Meli is one of Jenn and Dan’s go-to brunch spots, where the same manager will greet you with a smile every time and you’re guaranteed a sizable portion. Located in west River North, it boasts a robust food menu as well as a menu dedicated to fresh squeezed juices! Jenn recommends ordering the yuppie bowl or the pancake breakfast, and Dan recommends ordering the biscuits and gravy or the Buffalo Chicken Wrap and fries.
Beatrix offers breakfast, lunch, and dinner, but weekend brunch is it’s best offering — their lemon ricotta pancakes can’t be beat! In the summer, enjoy a table outside right in the middle of Clark Street, several blocks of which have been closed to traffic since Spring 2020 and remain closed today for outdoor dining! Beatrix has locations in Streeterville and the West Loop neighborhoods as well, both excellent!
La Colombe has brick and mortar stores in only six states and Washington D.C., and Chicago is lucky enough to have five different locations (Jenn has been a proud patron of all five)! If you need a coffee fix — hot, cold, or in between — you need to check them out! Jenn’s go-to location is in Chicago’s Gold Coast (one block away from her former apartment building!), and she highly recommends ordering their Oat Black and Tan: their smooth cold brew mixed with their signature oat milk draft latte *chef’s kiss*.
There are many donut shops in Chicago, but Jenn and Dan have a special place in their hearts for Do-Rite, which never disappoints. If you’re in the mood for a walk and a sweet treat, check out their West Loop location and pick up either a Blueberry Crumb (Jenn’s favorite), a Buttermilk Old Fashioned (Dan’s favorite), or both!