Seasons and when to go
Chicago month by month, and what to wear.
Chicago in September
If you can pick any month for a first trip to Chicago, pick September. The humidity breaks, the lake is still warm enough to wade into, the patios are full, and the families who packed the Riverwalk…
Chicago in November
November is really two months in Chicago. For the first three weeks, the city is gray, quiet and cheaper than it's been since spring, and you'll have the museums nearly to yourself on a weekday.
Chicago in December
December is the one winter month when people come to Chicago on purpose. The Christmas market is up in Daley Plaza, the tree is lit in Millennium Park, the L runs a train covered in lights with Santa…
Chicago in Winter
Winter is generally unpleasant in most northern cities, and in Chicago it's no exception.
Things to Do in Chicago in Fall
I can't say it enough. Fall is my favorite time of year in Chicago. The sweltering days of summer have passed; the freezing cold temperatures of winter have yet to arrive.
Things to Do in Chicago in June
June is when things really get into full swing in Chicago and in many ways, it's the ideal month to plan a visit.
Things to Do in Chicago in December
December in Chicago is a lovely time. The city seems to sparkle with all the holiday lights that twinkle from Daley Plaza to the Lincoln Park Zoo.
Things to Do in Chicago in November
The calendar of fun things to do definitely begins winding down in November. Gone are the summer festivals, concerts and sporting events.
Chicago in October
October is one of the best months to be in Chicago, though the weather can be a bit unpredictable.
Things to do in Chicago in October
October can be a lovely month in Chicago. The excitement of the many weekend neighborhood festivals may be gone (along with many of the tourists) but there's still plenty to do before winter sets in.
Things to do in Chicago in September
September is one of my favorite months in Chicago. The stifling summer humidity dissipates, but the crippling winter cold is still a few months away.
Things to Do in Chicago in August
By the time August rolls around, Chicagoans know that their days of summer are numbered.
Things to Do in Chicago in May
As the temps continue to rise in Chicago, restaurants begin to open their outdoor decks, sidewalk patios, and hidden beer gardens, boats fill the marinas, and the sounds of the "7th Inning Stretch"…
Things to Do in Chicago in April
April signifies the real start of spring in Chicago and it's one of the best times to visit the city.
Itinerary: A Long Weekend in Chicago in Spring
Many visitors to Chicago choose to come for a long weekend or just three to four days.
Chicago in Summer
During no season is Chicago at its best more so than in summer. It's the height of tourist season, but June through August also offer the most to see and do.
Chicago in August
August in Chicago is typically hot, sweaty, sticky and crowded. Along with July, it is one of the peak months for tourism in Chicago. And it's no wonder.
Chicago in July
Chicago's summers are short, hot and generally get into full swing by July. This is peak tourist season - there seems to be a street festival every weekend (including the massive Taste of Chicago),…
Things to Do in Chicago in March
March's social calendar is dominated by one event - St. Patrick's Day. One of the most popular holidays in the city, it is celebrated by young and old, Irish and not.
Chicago in Spring
After the dreary cold days of winter, spring in Chicago seems doubly welcome. As the temperatures rise, so do people's spirits as they look forward to the warm sunny days of summer.
Chicago in June
June is one of my favorite months in Chicago. Summer is definitely here, but the extreme heat and humidity of July and August have yet to descend upon the city.
Chicago in May
Spring is one of the best times to visit Chicago. In May you'll fine fewer crowds than during June, July and August, and flight and hotel prices are often lower.
Things to Do in Chicago in February
February can be a pretty bleak month in Chicago. The holidays have long since passed, and it's cold outside. Really cold.
Chicago in April
April signifies the real start of spring in Chicago. Finally the bitter cold and winds (and random snow storms) of March give way to bright sunny days that increase as the month goes on.
Chicago in March
By mid-March, Chicagoans are starting to see the light at the end of the tunnel that is Chicago's cold, dark, dreary winter.
Chicago in February
Winter is off-season in Chicago, and once you step outside in the city you'll understand why. It's cold, there's just no denying it.
Chicago in January
If you take into account overall monthly averages, January is the coldest month in Chicago.
Things to Do in Chicago in January
Chicago slows down a bit in January. The excitement of the holidays are over and most people are just trying to make it through the next month or so without contracting cabin fever from spending so…
Things to Do in Chicago in Winter
Chicago’s main tourist season takes place from May to October with significantly less visitors coming to the city during the cold winter months.
What to Wear in Chicago in Winter
Tourism in Chicago sees a pretty big dip in the months of January, February, and even into March (with the exception of St.
What to Wear in Chicago in Fall
Fall is a beautiful time to visit Chicago, and one of my favorite seasons in the city. The days are warm, with just a bit of crispness to the air, and nights slowly begin to turn cold.
Ways to Beat the Heat in Chicago
As cold as the weather in Chicago gets in winter (and I mean brain-freeze, I-don't-want-to-leave-the-house-until-March, is-that-an-icicle-forming-on-my-eyelash kind of cold), it seems to get equally…
Things to Do in Chicago in July
Summer is in full swing in Chicago - there's a festival every weekend, tons of farmer's markets to choose from, the beaches are packed and the best alfresco restaurants have their patios and decks up…
Things to Do in Chicago on Rainy Days
Summer storms are common in Chicago, and while your visit might fall during a hot, sunny dry spell, you may also find that every day of your vacation is marred by torrential rainfall and frightening…
What to Do in Chicago in Summer
Ask any Chicagoan (okay, maybe not this one - I can't handle extreme heat) and they'll tell you summer is by far the best season to be in Chicago.
What to Wear in Chicago in Summer
Packing for a trip to Chicago can be challenging, and while it's much easier for a summer trip than for a visit in the spring, it can still be difficult to cover all your bases, especially if you…
What to Wear in Chicago in Spring
One of the most common questions asked by tourists coming to Chicago is what to pack.
What to Do in Chicago in Spring
Spring is one of my favorite times of year in Chicago (a close second to autumn; I just can't handle the extremes of summer and winter). The days get warmer, but not hot.
Five Reasons to Spend Spring Break in Chicago
Forget Cancun, Fort Lauderdale, and all those other typical Spring Break destinations.