Chicago is a great city, but we all know it's better during certain parts of the year. The summers are hot but euphoric, the winters are frigid and depressing, and everything in between is a crapshoot. It's clear that all months are not created equally here, so we took the liberty of ranking them. From the weather to the quality of things to do to the general vibe around town, we considered it all in making this list.
1. September: The month that bridges the gap between Chicago's best two seasons (summer and fall) is undoubtedly the best. The brutal humidity of summer finally starts to fade, and by the end of the month the air turns crisp enough to don a light jacket. It's the last month in which you can take a swim on the city's beaches, which close on Labor Day, but that's just the tip of the iceberg. Riot Fest closes out the music festival season this month, the city's biggest art fair in Expo Chicago is nothing short of extraordinary, and you can squeeze in a whole mess of great events before the city begins its transition into an uninhabitable tundra.
2. July: Even though summer starts in June, it's not reliably warm then. July, though, is a sweltering 31-day stretch during which Chicagoans get straight up high off of Vitamin D. Both Pitchfork and Lollapalooza take place during the month (granted, sometimes Lolla kicks off or carries into August), and there are more free street festivals than one can even wrap their head around. Summer in Chicago reminds locals why they fell in love with the city in the first place, and July is the epitome of that.
3. May: Chicagoans finally break out of their cocoons in May and start shooting good, old-fashioned Midwestern grins at one another again. Memorial Day weekend is a bit like a reunion where friends who refused to commute to far away neighborhoods in winter finally see one another again. With the exception of a few fleeting cold stretches, the weather in May in Chicago is downright delightful—it's a breath of fresh air before the city becomes one massive sweat gland.
4. October: The weather during the first half of fall in Chicago can best be described as "crisp." Unlike spring, which is more erratic than a crazy ex-lover, October tends to be a smooth transition between the summer and winter. If Chicago's baseball teams fare well, all five of the city's major sports clubs play during the month. Halloween in the city gets way too freaky and weird, usually leaving the entire town hungover (in a good way) for the first week of November. But the best part about the month is the style—people can get fabulously creative in a few light layers.
5. August: August is no July—everyone in town is goddamned sick of the heat by the time the month rolls around. But it's hard to get sick of Movies in the Park and drinking on rooftops. With the Air and Water Show and a loaded-up schedule of day games for both the White Sox and the Cubs, it's also a time when tourists flock to town like a moths to a flame. Even though Chicagoans become a bit jaded about summer in August, everyone cherishes the last full month when they're able to wear shorts and sleeveless shirts outside.
6. June: Do Division, Ribfest, Taste of Randolph, Green Music Fest—the list goes on. June kicks off the summer's street festival season with a bang, and it allows Chicagoans to finally show their out-of-town friends what the city is all about. If you're not a pleasant person when June rolls around, then you have some serious issues to work out.
7. November: In November, you get a great introduction into the holiday season before it gets too cold outside. Christkindlmarket opens up, you're once again able to ice skate at outdoor rinks and the return of chilly weather gives you an excuse to fatten up on dark beers and greasy food.
8. December: If we didn't have the reprieve of the holiday season, shit would really hit the fan in Chicago during December. During the coarse month, you'll likely encounter at least a dozen people cursing the heavens over the fact that they already ruined a pair of shoes by way of rock salt. That group of friends in Rogers Park will start to realize they've been exiled because no one in their right mind is going to travel all the way up there in the dead of winter. If your family lives in a warmer climate, you'll at least have the opportunity to relish in some warmth during the holidays while the rest of us attempt to numb ourselves from the cold by listening to Mariah Carey's Christmas album for 12 days consecutively.
9. January: The new year tends to bring the realization that things are not going to get better anytime soon. The sun is a thing you vaguely remember. Instead of being introspective during your morning walk to the train, January forces you to focus on the fact that you cannot feel your face. One saving grace for the month is that it's in the heart of the winter concert season, with Tomorrow Never Knows the crown jewel.
10. April: April is a tease. It makes Chicagoans feel like Al Pacino in The Godfather: Part III (right when he thought he was out, they pulled him back in). Sure, the month will bless the city with a gorgeous day here and there, making residents believe that the cold armies of winter have retreated for good. But as soon as you make plans to grill out or go for a bike ride down the Lakefront Trail, April smacks you in the face with a week of nasty, cold rain.
11. February: A lot of Chicagoans would say February is the worst month in Chicago. After all, it tends to be the coldest in the city. But even though it's awful outside, it's reliably awful. February never lets you down because, well, the expectations are already so low. It's also the shortest month of the year, so even though seasonal affective disorder becomes an epidemic in town, it's over relatively quickly.
12. March: If April in Chicago is a tease, March is straight-up Brutus. Just when you thought you had something to rely on, it stabs you in the back with terrible and unpredictable weather. Even more, daylight savings time begins this month, stripping us of one of our precious hours. The worst part of the entire month might be the events that take place downtown during St. Patrick's Day weekend—hordes of drunk children roaming the streets like zombies, disheartening anyone with an ounce of optimism left in their soul.