Things To Do
City Winery at the Riverwalk
A favorite spot of ours that we visited an hour before we got engaged! Enjoy a glass of wine at their walk-up bar on the riverwalk while you watch the boats pass by.
Pizzeria Portofino
A delicious meal right on the river with great summer spritzes and views of the city. A small taste of Italy with fun pizzas and pastas on the menu
Beatnik On The River
Minutes before the engagement, we were finishing up a delicious brunch at Beatnik. The eclectic, maximalist interior is the perfect setting for a great meal on the river and of course an awesome photo-op.
Portillo's & Barnelli's Chicago
It's not a trip to Chicago without Portillos. If you're looking for a quick bite, hangover food, or just a classic Chicago hot dog, Portillos is the place.
Sweet Mandy B's Bakery
Forget all the other recommendations - just go to Sweet Mandy B's. You've never had a cupcake this good in your life and you're missing out if you don't stop by. We highly recommend SMB's for your sweet treat trip while in town.
Starbucks Reserve Roastery
The world's largest Starbucks is right downtown on Michigan Avenue. It is 4 floors of special menu items, a Starbucks cocktail bar, and a little history of the business itself.
Chicago's First Lady
The Chicago Architecture Tour is a fan favorite. It is an hour long boat tour on the Chicago River highlighting prominent buildings and city history. Running ~$60/person, it is a great way to see and experience the city especially if it's your first time visiting!
Navy Pier
A walk around Navy Pier is one of the best FREE activities in the city that gives you some of the most beautiful views of the skyline. On the pier you can find plenty to do for additional costs including the ferris wheel, restaurants, botanical gardens, art, museums, shops, and much more.