One of the best ways to see the city!
Flyover is a Mary Schelble FAVORITE and we all love this Chicago experience too! We highly recommend making a trip down to Navy Pier (20 minute walk from the Drake and 5 minute bike ride on the Lakeshore path) to enjoy the Flyover in Chicago. You will not regret it!
The pedestrian friendly south bank of the river stretches for over a mile (starting from Lake Michigan) and is filled with cafes, wineries, bars, public art, monuments, and a ton of excursions on the water.
The Lakeshore Trail is a must when in Chicago - beautiful views of the lake, city and beach. There is a tunnel path right across the street from The Drake that will take you over to Oak Street Beach and Whispers Bar & Grill. Depending on far north you walk, pop into Theater on the Lake for a Coors Light or cocktail!
Sophisticated French Vietnamese fusion in a palm-filled dining room plus a terrace overlooking bustling Oak Street.
Quintessential Chicago steakhouse in The "Triangle". Lively atmosphere, great cuts of steak, seafood, proper martinis...and of course the people watching.
This rooftop bar perched atop the LondonHouse Hotel has some of the most beautiful views of downtown Chicago.
Jen's favorite for a weekend coffee & croissant. You may have to wait but the line moves quick.
Farm-to-table restaurant with Southern flair in historic carriage house in Chicago's Gold Coast. One of our favorites for brunch, especially being on the patio. The fried chicken and waffles are some of the best you'll ever have.
Cherished family owned dive bar in the Gold Coast, known for their extensive Christmas decorations during the holiday season.
If you can't find Jen, then the first place to look is the Lincoln Park Zoo. Lincoln Park is where Jen & Casey both live and it holds a special place in their hearts. The Lincoln Park Zoo is a favorite for it's stunning grounds, florals and cute wildlife. Grab a drink and a snack at Cafe Brauer while taking in the views of the pond and honey comb!
Old-school tavern & barbecue (famous ribs) restaurant founded in 1932 & once frequented by Frank Sinatra. Jen's mom and dad had their first date here!
Sports parlor with excellent kitchen for brunch or dinner in the heart of Old Town.
Known for their deep-dish pizza, which is part of Chicago's iconic culinary scene. Yes, they do have thin crust as well. If you're looking for more pizza options and want to venture out more we love Piece Pizzeria (Wicker Park), Ranalli's (Lincoln Park), and DeNucci's (Lincoln Park). Robert's Pizza & Dough Company is another town favorite (Streeterville).