I have always heard so many wonderful travel stories about Chicago and finally had an opportunity to visit “The Windy City” while attending a painting class.

The problem was, would my bucket list of activities, accumulated from recommendations from friends as well as online research, fit comfortably into two days? As it turned out, we arrived early evening, in time to see the sunset from the John Hancock Observation Deck (now called “360 Chicago), and departed 48 hours later after the Chicago Cubs game.

Would I have done anything differently? The weather was extraordinarily beautiful in mid-June that enabled us to enjoy bicycling four hours north to Wrigleyville. If time had permitted, I would have taken a full day for the bike ride. All in all, I couldn’t have imaged a more perfect two days in Chicago. Following are some photos in the order we did what I considered the best things to do in Chicago in two days:

Sunset Views of Chicago from the John Hancock “360 Chicago” Deck:

Chicago 360 Observation Deck North Shore

Day 1 Morning – Architectural Boat Cruise:

Chicago Architectural Boat Tour 1    Chicago Architectural Boat Tour 2

Day 1 Afternoon – Rock & Ride Bicycle Rental from Millennium Park – Rode along North Lakeshore Drive to Wrigleyville and returned bicycles to Navy Pier:

Chicago Bike Ride - Oak St Beach

Chicago Bike Ride - Navy Pier & Ferris Wheel

Day 1 Late Afternoon/Evening – Millennium Park: Concert at Pritzker Pavilion, Cloud Gate Sculpture aka “The Bean,” Crown Fountain; walked Michigan Avenue:

Chicago Concert at Pritzker Pavillion

Chicago Millennium Park - Cloud Gate Sculpture

Chicago Inside Cloud Gate-The Bean

Day 2 Morning – Chicago Institute of Art:

Chicago Institute of Art    Chicago Institute of Art - Jeff Koons Sculpture

Chicago Institute of Art - Jasper Johns

Day 2 Afternoon – Rode the Red Line to the Cubs game at Wrigley Field:

Chicago Cubs Wrigley Field Entrance

Chicago Cubs v. Diamondbacks Game

Affiliate links: