Things to Do in Chicago on a Rainy Day (for Grown-Ups)

Morning

The Art Institute: pick a wing or two

Lunch

Under glass at Cindy's or City Winery's enclosure

Afternoon

Frank Lloyd Wright's Oak Park studio (guided, indoors)

Evening

Andy's Jazz Club, the CSO, the Lyric Opera or Second City

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A morning at the Art Institute

Spend the wettest hours at the Art Institute of Chicago, one of the great art museums in the world and strongest in Impressionism and American art. It's big enough to fill a whole day, so pick a wing or two and pace yourselves. Book tickets ahead and go early, before the rest of the city has the same idea.

Lunch with a view, under cover

Two places let you watch the weather from somewhere warm. Cindy's, a short walk away on the 13th floor of the Chicago Athletic Association, is a glass atrium looking over Millennium Park and the lake. City Winery at the Riverwalk pours its own wines on tap and closes a retractable glass enclosure on cooler days. If the cloud is high, a drink at CloudBar on the 94th floor of 360 CHICAGO puts you above it all; if it's low, save it for another day.

An afternoon with Frank Lloyd Wright

Rain is a good excuse to see architecture from the inside. The Frank Lloyd Wright Home and Studio in Oak Park, about 30 minutes west, is seen on a one-hour guided tour of Wright's own house and studio; book ahead. Save the open-deck architecture river cruise (mid-March to late November in 2026) for a dry spell later in the trip.

A long, warm dinner

Book somewhere you'll want to stay for hours. Monteverde in the West Loop makes pasta by hand in the middle of the room, and Girl & the Goat on Randolph Street serves big-flavoured shared plates in a lively room. For a classic, clubby night, Gibsons on Rush Street has white-jacketed servers and giant desserts.

Indoor nights out

Chicago's evenings were always going to be indoors. Hear jazz over dinner at Andy's Jazz Club (a reservation covers one set), catch the Chicago Symphony Orchestra or the Lyric Opera, whose 2026/27 season opens with Don Giovanni from October 10 to November 1, or laugh at The Second City, with two mainstage revues on Friday and Saturday nights. Finish underground at Three Dots and a Dash, a tiki bar reached through an alley. Our Chicago at night guide has the late jazz and blues clubs.

Our advice

• Keep the day in the Loop: the Art Institute, Cindy's, Symphony Center and the Riverwalk are all a few minutes apart.
• Use taxis or rideshares for Oak Park, the West Loop and River North rather than walking between them in the rain.
• Check the forecast before booking 360 CHICAGO: low cloud can hide the view completely.
• Check current hours, show times and prices before you go.

Everything here was checked in September 2026. Club line-ups, cruise seasons and performance calendars change, so confirm before you go.