Chicago

606 trail bike ride

Elevated rails-to-trails across the northwest side. Sunset direction west.

Architecture river cruise

Ninety minutes of world-class buildings from the water. Docent-led boats only.

Art Institute lions visit

Chagall windows, Thorne rooms, lions out front for photos.

Blues night in Chicago

Kingston Mines till late. Two stages, no bad seat.

Chicago lakefront PR attempt

Dead flat, screaming crowds, personal best territory.

Deep dish knife-and-fork

Lou Malnati's buttercrust. Forty-five minute wait, zero regrets.

Deep dish vs thin crust day

One of each, no fence-sitting. Riverwalk stroll between rounds.

Garfield Park conservatory

Palm room in January beats everything. Free, warm, enormous.

Italian beef dipped in Chicago

Al's number one, hot peppers, stand-up counter only.

Jazz Showcase late set

Basement club, legends weekly. Late set, front table.

Millennium Park morning skate

Open-air rink with the Bean watching. Rentals on site.

Pilsen taco and mural walk

Murals for miles, tacos every block. Start at 18th and Halsted.

Second City improv night

Where SNL casts are born. Front row volunteers beware.

Skydeck Ledge sunrise

Glass box over the city, first slot empty. Book the earliest entry.

Wrigley bleacher day

Old Style, seventh-inning stretch, day game. Bleachers for the vibe.

606 trail bike ride

Elevated rails-to-trails across the northwest side. Sunset direction west.

Art Institute lions visit

Chagall windows, Thorne rooms, lions out front for photos.

Deep dish knife-and-fork

Lou Malnati's buttercrust. Forty-five minute wait, zero regrets.

Italian beef dipped in Chicago

Al's number one, hot peppers, stand-up counter only.