This tour is a must-do for Chicago first timers! Caitlin & Jack have both been on this tour numerous times, and it's always a hit with guests. At 90 minutes, it's a great way to see some of Chicago's architectural highlights without having to navigate yourself around the city. Beverages are available for purchase onboard, too!

A round of darts at Flight Club is a fun way to kill some time! Guests have access to their own personal darts stall where you can try your hand at various games. The space is upscale and offers a full bar and a food menu.

Although reservations are recommended, walk-ins can be accommodated on a first come, first served basis.

Viaggio is a local gem in Chicago's West Loop neighborhood, just a quick Uber/taxi ride from the Loop. This Italian restaurant became a favorite of the bride & groom when they moved to the neighborhood. Jack & Caitlin have enjoyed many dinners with friends and out-of-town guests here, and it's where they celebrated their engagement!

Chicago has an awesome comedy scene, and one of Caitlin & Jack's favorite date night activities is seeing a comedy show together. The Comedy Bar, Zanie's and Second City are all great choices with various show times!