Trip | Chicago in 3 days with friends | Chicago, IL | 3 days
Day 1 – The Loop and the river
10:00 AM | Do | Millennium Park, 201 E Randolph St, Chicago, IL | See Cloud Gate (the Bean) before the crowds
11:00 AM | Do | The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL | Give it two to three hours
2:00 PM | Eat | Portillo's, 100 W Ontario St, Chicago, IL | Chicago-style hot dogs and Italian beef
3:30 PM | Do | Chicago's First Lady Cruises, 112 E Lower Wacker Dr, Chicago, IL | The Chicago Architecture Center river cruise; book ahead
7:00 PM | Eat | Lou Malnati's Pizzeria, 439 N Wells St, Chicago, IL | Deep dish, butter crust
Maybe | Do | 360 Chicago, 875 N Michigan Ave, Chicago, IL | Night views from the 94th floor
Day 2 – Lincoln Park and the lakefront
10:00 AM | Do | Lincoln Park Zoo, 2001 N Clark St, Chicago, IL | Free
11:30 AM | Do | North Avenue Beach, 1600 N Lake Shore Dr, Chicago, IL | Walk out to the end for the skyline
1:00 PM | Eat | Pequod's Pizza, 2207 N Clybourn Ave, Chicago, IL | Pan pizza with the caramelized crust; expect a wait
3:00 PM | Do | Wrigley Field, 1060 W Addison St, Chicago, IL | Catch a Cubs game, or take a ballpark tour on off days
7:30 PM | Eat | Au Cheval, 800 W Randolph St, Chicago, IL | Burgers on the West Loop's Restaurant Row
Maybe | Do | The Second City, 1616 N Wells St, Chicago, IL | Improv comedy most nights
Day 3 – A big museum and the view
9:30 AM | Do | Museum of Science and Industry, 5700 S DuSable Lake Shore Dr, Chicago, IL | Plan on the whole morning
1:30 PM | Eat | Billy Goat Tavern, 430 N Michigan Ave, Chicago, IL | The original is downstairs on Lower Michigan Ave
3:00 PM | Do | Skydeck Chicago, 233 S Wacker Dr, Chicago, IL | Step out on The Ledge, 103 floors up
Maybe | Do | Navy Pier, 600 E Grand Ave, Chicago, IL | The Centennial Wheel and lake views