The Second City is a Chicago institution - and the site of our first date!

The Second City is a must-do for those who love comedy! It's the oldest improv theater group to be continuously based in Chicago (celebrating over 65 years). Alumni include Steve Carell, Tina Fey, Amy Poehler, Mike Myers, Chris Farley, Tim Meadows, Stephen Colbert, and many others! If you could use a good laugh, we highly recommend planning a stop.

If you'd like to enjoy the entirety of the Isaac-and-Becca's-First-Date-Experience, hit Chicago Pizza and Oven Grinder Company for dinner beforehand - be advised, it's cash only!

Spanning over 18 miles of Lake Michigan's western coastline, the Chicago Lakefront Trail is one of Chicago's true gems.

Whether you want to grab a walk, a run, or a bike ride, make your way to the lake and you'll find the path!

If you want to make an afternoon out of it, pack a picnic and set up in one of the many grassy areas along the path - it's a wonderful way to soak in the city (and hopefully some sunshine)!

Featuring the architectural icon "The Bean," Millennium Park is a Chicago staple - a can’t-miss attraction for any Chicago visit.

Bring your walking shoes and enjoy over 24 acres of fountains, gardens, community events, public art, rock climbing, and green space.

If you find yourself getting hungry, there are always lots of food vendors in and around Millennium Park - it's a great time to grab a Chicago Dog! We also recommend Cindy's Rooftop for anyone looking to grab a drink and enjoy a birds-eye view of the park. Be warned - Cindy's gets very busy on summer days!

A fan favorite! There are many different companies who offer the famous architecture boat tours, which take you up and down the Chicago River and teach you a few things along the way.

We recommend taking the Chicago Architecture Center's First Lady Boat Tour. Led by docent volunteers from the Chicago Architecture Center, this 1.5 hour tour offers all of the major highlights! All CAC tours offer a full-service bar on board, restrooms, and temperature-controlled cabins for those who don't want to sit outside.

You haven't truly experienced Chicago if you haven't eaten entirely too much food.

For deep dish pizza, our go-to for ordering in is Lou Malnati's. They also do a great thin crust! If you don't mind a bit of a wait, and you're looking for a more neighborhood-based experience, Pequod's is for you. For any deep-dish haters, Piece Pizza offers a great New Haven-style pizza and an opportunity to spend some time in Wicker Park, a beautiful and vibrant Chicago neighborhood!

If you're searching for a Chicago Dog, we recommend hitting Byron's. There are multiple locations, but we recommend the stand at Irving Park and Sheridan - grab a hot dog and take a stroll around Wrigley Field.

Looking for something different? Chicago is one of the best food cities in the world - you can't go wrong! Whether you decide to explore everything that the West Loop has to offer, or you want to venture into one of Chicago's 177 other neighborhoods, you'll find great meals abound wherever you go. Some ofour favorites include:

Brunch:

Southport Grocery

Breakfast House

Yolk

3 Arts Club Cafe

Dinner:

Hopleaf

Topo Gigio

Little Bad Wolf

Galit