When should you visit Chicago?

+Lowest hotel rates of the year and the Art Institute practically to yourself.

–Brutally cold, short days, lake-effect wind makes it feel worse than the thermometer says.

+Still dead quiet and cheap, with cozy jazz clubs and deep-dish weather.

–Same bitter cold as January, just with slightly longer days.

+The city wakes up before the bulk of tourists arrive.

–Weather swings wildly, and the St. Patrick’s Day river-dyeing weekend packs downtown.

+Mild air, longer evenings, riverwalk restaurants reopening.

–Still unpredictable — a warm day can be followed by sleet.

+Chicago’s best weather window — warm days, cool evenings, rooftops back in full swing.

–Rates and crowds start climbing fast as the season turns.

+Long daylight, lakefront beaches open, Blues Fest energy.

–Peak-season pricing kicks in and hotels fill on festival weekends.

+Maximum energy — fireworks, festivals, patio season at its peak.

–Hot and humid, and Lollapalooza (Jul 30–Aug 2) pushes rates to their yearly high.

+Air and Water Show over the lake, Chicago Gourmet, full patio season.

–The rainiest month of the year, on top of peak summer crowds and prices.

+Warm, dry, comfortable days with noticeably thinner crowds and softer rates than midsummer.

–Good hotel rooms still book up fast on nice weekends.

+Crisp, clear walking weather and Chicago’s architecture at its best with fall color.

–The Chicago Marathon weekend (Oct 11) fills hotels and closes major roads.

+Quiet and good value once Thanksgiving week passes — museums nearly empty.

–Cold sets in fast, and Thanksgiving week itself brings a short, sharp crowd spike.

+Christkindlmarket and Mag Mile lights make the city genuinely festive.

–Cold, and the week around Christmas/New Year’s pushes rates back up.