A beautiful spot for a walk, drink, or bite to eat along the water. Grab a glass of wine, rent a kayak, or simply enjoy the views of Chicago’s iconic architecture.
Lane and William highly recommend! These tours offer a fun and fascinating look at the city’s skyline from the river.
A delicious Italian restaurant on the River. Also where William asked Lane’s parents for their blessing to marry her!
Where the show "The Bear" takes place, offering another iconic Chicago dish: the Italian Beef sandwich.
Stroll through Millennium Park, snap a photo at “The Bean,” and enjoy the gardens, fountains, and public art in the heart of downtown.
One of the best art museums in the world, home to classics like American Gothic and Nighthawks.
Dive into one of Chicago’s most iconic attractions, home to over 30,000 aquatic animals from around the world.
Rent a bike, join William for a run, or take a scenic walk along Lake Michigan for some fresh air and gorgeous views.
No trip to Chicago is complete without trying the city’s iconic deep-dish pizza. There are plenty of great spots around town, but Lou Malnati’s is our personal favorite!
Yes, we have a beach in Chicago :)
A lively brunch spot in Chicago’s Gold Coast neighborhood.
Where Lane spent way too many nights during her Chicago days.
A true Chicago classic! William highly recommends the Guinness.
Lane’s old neighborhood! Great shopping, cafes and restaurants!
A charming sports bar in Lincoln Park where Lane’s parents met!
A great brunch spot in Lincoln Park. Also where William met Lane’s parents for the first time.
This legendary comedy theater has launched the careers of icons like Tina Fey, Steve Carell, and Bill Murray—and it’s still cranking out sharp, smart, and hilarious sketch and improv shows every night.
Delicious Mediterranean food in the West Loop neighborhood.
Although the staff may not be the friendliest, the Chicago style hotdog is a must!