Things To Do
Chicago River Boat Architecture Tour
Our favorite Chicago activity! Hop on board and enjoy a guided tour of Chicago's beautiful architecture. Local tip - there is a bar on the lower deck!
Flight Club
Upscale darts spot with great food, drinks, and music! Located on the famous Wacker Drive, you'll have incredible views of the city and the river. This is a great spot for after the boat cruise as it's just a 10-minute walk from the dock.
Chicago Riverwalk
With iconic views of downtown, many of our Chicago adventures incorporated a stroll along the Riverwalk.
Etta - River North
Known for their Italian cuisine and wood-fired pizza, and where we dined the night of our engagement!
Michigan Avenue
Walk Chicago's Magnificent Mile - tons of great shopping, sightseeing, and food! We recommend starting at Nordstrom and walking north until you reach Lake Shore Drive.
Lake Shore Drive
Walk or bike down the beautiful Lake Shore Drive! We recommend the walk from Oak Street Beach to North Ave Beach, which has a large walking/biking path for everyone to enjoy. The views of the city are amazing from the path!
Au Cheval
Voted "Best Burger in America", Au Cheval is a must! The restaurant does not take reservations, so we recommend putting your name on the list and then walking or barhopping down Randolph St until your table is ready. Wait times will vary between 2-4 hours so you'll have time to explore the city and work up an appetite!
LUXBAR
Located in our old neighborhood, Gold Coast, this was our go-to spot for brunch, lunch, or dinner. Josh's all time favorite buffalo chicken salad!
Cabra
On the rooftop of the Hoxton Hotel in West Loop, Cabra Cevicheria is a Peruvian-inspired restaurant by our favorite Chicago Chef, Stephanie Izard.
Marvin's Food & Fuel
Within a 10 minute walk from the Hyatt House, this brunch staple offers a quintessential breakfast sandwich along with a bottomless brunch.
Big Star
Located in the heart of Wicker Park, Kelly's first neighborhood in Chicago, we frequently found ourselves enjoying tacos and margaritas on their patio.
Sparrow
Where we continued the celebration the night of our engagement. Also known for Kelly's favorite dirty martini!
The J. Parker
Located on the rooftop of Hotel Lincoln, this bar and restaurant offers beautiful views of Lincoln Park and Lake Michigan.
Sprinkles Chicago
Our most frequented spot for a sweet treat (especially because this location includes a cupcake ATM open 24/7). Located at Michigan Avenue and Rush Street, this is the perfect place to stop after shopping along Chicago's historic Magnificent Mile.