Things To Do
Pizzeria Portofino
Our favorite spot to eat on the river! Wonderful cocktails and appetizers. Make sure to make a reservation well in advance, as this is a popular restaurant!
Pequod's Pizza
This is our favorite spot for authentic Chicago deep-dish pizza, so check it out if you want to give it a try!
Cindy's Rooftop
Spectacular views of Grant Park and Lake Michigan! This is one of the most famous rooftops in the city, so if you want to go, make sure to have a reservation!
LH Rooftop
Another wonderful rooftop, this one looking over the Chicago River and the historic skyscrapers that make up our skyline. Reservations definitely encouraged!
The J. Parker
This rooftop is our favorite! The views of Lake Michigan and Lincoln Park are the best in the city. No reservations, walk-in only! Check it out at sunset if you want to be truly wowed.
Butch McGuire's
On the other hand, if you are looking for a classic Chicago pub, this is a great spot! Spirited, old-school Irish bar. The street that Butch McGuire's is one has many pubs and bars that are fun for a night out (including the spot we met)!
Gilt Bar
One of the coolest restaurants in the city, Gilt Bar has a wonderful atmosphere, cocktails, and burgers. Plus, it has its own speak-easy downstairs you can check out!
Chicago River Boat Architecture Tours
If you have any free time, this is a must do! Experience the magic of Chicago's beautiful architecture from a boat cruising down the Chicago River. Every person we've taken has agreed it's one of the best things to do as a visitor!
Lakefront Trail
Another great option if you have any free time in the city. The Lakefront Trail over 18 miles long and borders the beautiful Lake Michigan. There are many bikes (Divvy/Lyft) to rent that you can ride up and down the shoreline. Additionally, there are spots along the way to stop and get drinks and snacks.
Just Walk Around!
Chicago is an extremely walkable city, and one of the best ways to experience it is to just explore! We recommend checking out the Lincoln Park, Gold Coast, and the Streeterville neighborhoods while you're here.