Stop by Annette’s for a sweet treat, but make sure you bring cash! This is one of Lauren’s and Andy’s most visited spots in the summer. Andy’s go-to is the black cherry Italian Fro-Yo, and Lauren’s is the coffee caramel chip.
Explore Lauren’s & Andy’s street and do a little shopping. Some of their favorite spots are mugsy (for men), bliss & belle, hotel chocolat, and gorjana.
Take a walk on or bike the 26-mile lakefront path. Some fun places to stop along the path are The Dock at Montrose Beach, Clock Tower Cafe, Castaways, Shore Club, Reggie’s, South Shore Social, and Pier 31 (honorable mention as this was where Lauren & Andy caught the boat that Andy proposed on)
Catch a cubs game at the friendly confines on Friday at 1:20, or if you’re feeling risky, Saturday at 1:20. Don’t miss the chance to grab a Chicago Handshake before at Murphy’s Bleachers. If you order a hot dog, make sure it’s a Vienna beef, and only apply ketchup at your own risk.
There are tons of companies that do architecture boat tours on the Chicago River. Lauren and Andy have done the Wendella tour (linked below) and had a great time. Plus, kids under four are free! If you have time, grab a drink and bites at the Northman while you’re over there.
Goose Island Pub is located next to the Salt Shed music venue, with a skyline view along Chicago River. It's a great spot to grab beers and a burger. Lauren’s go-to order is a hazy beer hug and a smash burger, and Andy’s is a 312 and a grilled cheese.
If you’re in the mood for Chicago’s famous deep dish pizza, Lauren’s and Andy’s favorite spot is Pequods. If you have never tried Giardiniera on pizza, you know what they say, when in Rome!
As seen on the Bear, Mr. Beef is a Chicago staple serving Italian beefs for over thirty years!
Also featured on The Bear, Kasama’s breakfast sandwiches cannot be beat. We would recommend ordering ahead for pickup, otherwise you will likely be waiting in a line. It is also home to Lauren’s and Andy’s favorite tasting menu for dinner.
The world’s largest Starbucks featuring five floors, including a rooftop terrace. Be sure to hit the third floor’s experimental coffee bar and the fourth floor’s cocktail bar for an espresso martini or matcha margarita (Lauren's personal favorite).