June 27, 2026
Chicago, IL
Cassie & Ryan
Things To Do
Chicago Activities!
Architecture Tour: Cruise along the Chicago river on one of the many boat tours! Lakefront Trail: take a walk along Lake Michigan Sports: check to see if any local Chicago teams are playing near our date
Looking for a rooftop bar?
Check out these views! London House, Cindy's, The Robey
Where should we eat?
Check out some of our local recs! Au Cheval, All Together Now, Alla Vita, Chef Special, Galit, Leavitt Street Inn & Tavern, Mindy's Bakery, Paulie Gee's Logan Square, Topo Gigio, Will's Northwoods Inn
For all the days along the way