By George Hobica,  Chicago may be at its most popular during the steamy, sunny summers, but we know plenty of locals who've got nothing but love for the city during the fall months. And we totally get it. What's not to get, really – the weather's still decent, the trees turn lovely colors, the crowds have dwindled; no more crazy summer festivals clogging the downtown lakefront. Fall in Chicago is a sweet spot. An all too short one, though; the time to book a flight? That'd be now. And here's a short list of things we love to do there:

YOU CAN GET PHYSICAL New York has Central Park and the Hudson River, Los Angeles has Griffith Park and the Pacific Ocean. Chicago brings its best features (well, natural features) together in one spectacular, almost-unbroken chain of open spaces that front directly onto shimmering Lake Michigan. Any proper exploration of the lakefront must begin at windswept Northerly Island, just a short stroll from the tourist crowds at the Shedd Aquarium and the Field Museum. Particularly on a weekday, this former airport (hands up, who remembers Meigs Field?) is not only one of the most peaceful places for a stroll anywhere near the center of town, it's also one of the most picturesque. Bring a camera – the skyline and marina views are stupendous.

IT'S TOTALLY COOL Let's turn the clock back about twenty years. Could anybody have envisioned a Chicago that competed with the coasts on the coolness front? Well, it happened, particularly on the city's West Side, which bounced back from decades of anonymity to become pretty much where it's at, Midwest-wise. Once laggard neighborhoods such as Wicker Park and Bucktown now comprise the heart of what's essentially become Chicago's Brooklyn – a whole other city, a whole different vibe, just a short hop from the center of town. Start a nightlife tour of the area with early cocktails at the plush and civilized, speakeasy-ish Violet Hour cocktail lounge (1520 N. Damen Ave.); then head across the street for beers and tacos (or more cocktails) at the classy (but insanely packed) Big Star, spilling out of an old gas station (153 N. Damen Ave.). Consider yourself properly introduced.

IT'S SECOND TO NONE Los Angeles may have eclipsed Chicago population-wise decades ago, but the Windy City bows to nobody in the culture department – well, outside of New York, anyway. Some people prefer Chicago, where it's easier to keep track of just what is happening on any given day; one thing that's easily remembered is the fact that the outstanding Art Institute of Chicago is now the second-largest art museum in the country. It was always a must-see, now there's just more of it, thanks to last year's addition of the $300 million Modern Wing, designed by starchitect Renzo Piano.

PLAY THE MARKETS Speaking of makeovers and important Chicago institutions, have you seen the city's Maxwell Street Market lately? Do you even know what it is? Or was? Let's start with the latter – this used to be Chicago's Lower East Side – wholesale this, pastrami sandwich that; years of decline lead to the decimation of the neighborhood. While a lot of locals like to kvetch about how things have never the same after they tore everything up (and subsequently put in condos and big-box stores), those unburdened by knowledge of the past will love the market, now held right in the shadow of the Loop skyline, for its informal and fun feel. Come hungry – the best reason to visit is for some of Chicago's best street food, much of it authentically Mexican (S. Des Plaines St., south of W. Harrison St.).

SOME OF THE BEST PIZZA EVER So you don't like tacos? No problem; this is Chicago. You can eat whatever you want. What we're eating, lately: Pizza, a lot of it, from Nick Lessins and Lydia Esparza'stiny, one-oven operation on the North Side. The place is called Great Lake. You may have heard of it recently; this hip little pizza parlor got a one-way ticket to stardom last year, when GQ Magazinetapped them as the home of some of the best pies in these United States. Bemused bystanders wondered how a relatively new spot serving artisanal thin-ish pies--baked in a gas oven, yet! -in a city known for deep-dish and true thin-crust might have trumped tradition.Somepeople wondered if the reviewerhad lost his mind.After too many Great Lake pies to count, we'll weigh in and say that it's a safe bet that most of the doubters have never eaten here. Meticulously crafted from seriously good ingredients (we love the one with Wisconsin sheep's milk cheese andearthy cremini mushrooms) embedded incrust that's alternately chewy, pillowy and crusty all at once, this is pizza you'll never, ever forget. A lot of people hate Great Lake. A lot of people can go to Pizzeria Uno and leave us alone. To be fair, there are certain considerable obstacles on this particular pathway to pizza pleasure, ones that every potential diner should know about. For starters, you wait forever. You need to come in early, or not at all. (This is a one-man army; Lessins can only make so many pies in a night.) Only masochists try to dine in; there are but 12 seats in the appealing but ultimately kind of stifling room. Don't fret, though. Just come armed with a strategy. Ours? Be there right when they open, order, then go around the corner to In Fine Spirits (5418 N. Clark St.), order a couple of cocktails and forget about the fact that it'll be an hour or more until we eat. Or that we'll be eating in the car. Who cares, really. When the pizza's this good, you just suck it up (1477 W. Balmoral Avenue, 773-334-9270).

THE RIVER IS UP The most popular way to see the Chicago River tends to be via pricey sightseeing boat; we prefer to see the river and work up an appetite for things such as that pizza we can't shut up about (see above); one of the ways to do this is to head up to Chicago River Canoe & Kayak; rent a craft for around $15 an hour and plot a northbound trip up the river; that way, when you're tired, you can ride the current back to their North Side launch. If you prefer, the outfitter offers guided tours. Hurry – they close for the season on Oct. 31. They could stay open all year, but their insurance probably doesn't cover the rental of icebreaker boats.

THE LAKE IS THE LAKE We love Lake Michigan at any time of year, but if the trees are turning, we like it even more. Just a little over an hour from downtown Chicago, find yourself in some seriously pretty – and seriously quiet – countryside. Sure, navigating the industrial (and post-industrial) mess that is Northwest Indiana can be a bit of a bear, but once you cross the state line into Michigan, you're right in the middle of Harbor Country, home to charming towns like New Buffalo and beautiful state parks such as Warren Dunes; it all adds up to one of the best excuses we can think of for renting a car at the airport.

THE DINING IS FINE Chicago may be famous for pizza, but it is also one of the best fine dining cities in the Western Hemisphere right now, thanks to chefs that know now to balance celebrity with commitment to quality in the kitchen, chefs like Grant Achatz (Alinea), Rick Bayless (Frontera Grill, Topolobampo, Xoco) and, more recently, Top Chef 4 winner Stephanie Izard (The Girl & The Goat). The biggest news this year, though, is the opening of Next, an accessible, world cuisine-exploring spot conceived by Grant Achatz. Achatz is known around the world for his inventive brand of molecular gastronomy, served prix-fixe in a formal Halsted Street townhouse-style restaurant; this new joint will feature rotating menus; dinners will be ticketed – you reserve and pay in advance; subscriptions will be available. What's one of the world's most acclaimed chefs doing, tinkering with affordable and fun, not to mention cocktails, which will be served at the adjacent bar, called Aviary? We're as curious as anybody – so far, details are few and far between, though the opening date is promised to be fast- approaching. Track the project on the restaurant's Facebook page, or stalk the actual space, steps out of the Loop (953-955 W. Fulton Market St.). In the meantime, we'll be at Bayless' casual Xoco, ordering some of the best Mexican street food we've ever had – on either side of the border. Wait, did we just say that? Yes. Yes we did (449 N. Clark St.).

Looking for low airfares to Chicago? Here's a current listing from all over the US.

All products and services mentioned on Airfarewatchdog are independently selected by our team of expert travelers. If you buy something through our links, we may earn an affiliate commission.

More Stories You'll Love