Nailing down a definitive Chicago bucket list is about as easy as, uh, something that's not super-all-that-easy. And we should know, seeing as how we... totally did exactly that: here are 35 essential things every Chicagoan has to do before they die. Or move to another city (basically dead to us). Or relocate to the suburbs with the kids (basically dead inside).
The good news? You don't even need to tightrope walk between skyscrapers.
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Willis Tower is still cool in our book (even though we still refuse to call it that), but the Hancock offers even better views and stiff drinks at its famous 95th floor lounge and restaurant. Not to mention one of the city's must-poop bathrooms. Pro tip: better hit the ATM first.
Now that Hot Doug’s has shuttered its doors (and shattered our hearts), Superdawg is probably where you’ll want to take all your visiting friends for the culinary masterpiece that is the Chicago-style dog. The classic spot hasn’t changed its recipes since 1948, and remains one of the few drive-ins around town.
Founded in 1954, the Lyric Opera of Chicago remains one of the leading opera companies in the country. Regardless of your thoughts on opera, every Chicagoan should visit this cultural institution at least once. There’s a reason it’s averaged a 95% attendance rate since 1988.
Due to the great concerts it offers throughout summer -- thanks to the expertly curated Downtown Sound and more experimental Loops & Variations series -- the Jay Pritzker Pavilion remains the choicest picnic spot in a very picnic-friendly city. And the #1 reason to visit the Loop.
While we usually advise against frequenting the suburbs, particularly for concerts, a booze-fueled trip on the Metra to see live music at Ravinia is a must for any summer Chicagoan. Just make sure to bring enough wine and cheese to feed a French battalion/you and your buddies.
Not only is the Green Mill one of Chicago’s oldest bars and a famous Capone hangout and movie location, it’s also one of the country’s premier destinations for live jazz. Tank up that DeLorean, because you’ll be traveling back in time.
Montrose Point isn’t just a bird sanctuary. It also offers the best damn view of Chicago’s skyline that doesn’t involve you trying to outsmart Eastern European tourists for seating at some Downtown hotel rooftop bar.
Billing itself as the “World’s Largest Jazz and Blues Record Store,” Jazz Record Mart has more records than there are dollars in the Pritzker family’s bank accounts. Actually, that’s definitely not true.
Every second Friday, visitors can check out great local art while strolling through one of Chicago’s most colorful neighborhoods. It’s like the currently on-hiatus First Fridays at the MCA, but cooler 'cause it's in Pilsen.
The Chicago Pedway doesn’t just offer year-round protection from the elements. It’s also stocked with bars, restaurants, and shops. We recommend stops at M Bar and the Rise N Roll Amish Market pop-up.
15. Close down a 4am bar
Whether you’re shredding your vocal chords to Journey at the Hangge Uppe, kickin’ it at Carol’s, or making bad decisions at Burton Place, there’s no feeling like asking yourself “why are they kicking everyone out of the bar” and then realizing “oh, it’s 4am”. No need to end the night though. Head to the Diner Grill.
Participate in hardcore aerobatics, dogfights, and simulated combat in an Italian fighter plane... all while donning a way-cool, Top Gun-style flight suit. It’s like your own personal Chicago Air & Water show, with you in it.
For the ultimate Ricky Bobby experience, shake and bake your way to Joliet’s 1.5mi NASCAR track, where you’ll strap into a race car and hit speeds up to 165mph (without any annoying red light cameras nabbing you for speeding). Choose your own adventure, anywhere from eight to 80 laps.
Whether you had to splurge on the tickets yourself or just happened to know a guy, everyone deserves the feeling of staring back at a packed stadium and saying “I have better seats than ALL of you.” Note: just use your inner monologue to say this. Out loud is poor form. If it’s a hockey game, getting to pound on the glass is a huge bonus.
Note: by “do,” we do not necessarily mean “complete”. Not all humans were meant to run 26.2 miles consecutively. In fact, the first guy who did it died! But if you CAN complete it, it’s damn impressive, and at the VERY least you should drag your doughy, hungover mess of a body out of bed at least once to cheer on the people who are actually running.
Every July, 350+ sailboats depart from the Chicago Lighthouse near Navy Pier for the 289-nautical-mile trip to Michigan’s car-free Mackinac Island in the world’s oldest annual freshwater distance race. Why shouldn’t one of them be you one of these years?
Not just any submarine. The German U-505 Americans captured during WWII that’s now resting comfortably at the Museum of Science and Industry. Take that, Nazis.
22. Eat that extra slice of deep dish
Lou's, Giordano's, Pequod's... you can get it at any of these places honestly, but the idea here is to reach that point where you say to yourself "it is medically inadvisable for me to eat another piece of this". Then you ignore yourself, inhale another piece, and take a seven-hour, cheese-induced nap. Then and only then have you had the full deep dish experience.
You live in the comedy capital of the world. If you take in a Second City performance there’s a good chance you’ll see someone who ends up on SNL one day, or, at the very least, a Sonic Commercial. But the real rush will come when they ask for an audience suggestion and improvise a hilarious scene to your well-timed shot of “marmots”.
This isn’t really one you plan for. It has to happen naturally. Maybe you packed into Old Town Ale House after the Second City. Maybe you’re checking out a friend’s band at The Hideout, or holding court on the Happy Village beer garden. You feel the hunger, and suddenly that glorious cooler appears and you devour a bag full of tamales with green salsa before you even know what happened, and all is right in the world again.
There are innumerate places to get a flawlessly made drink in Chicago, but the most bucket list-worthy has to be the Violet Hour, a temple of cocktail artistry to which many other find Chicago bars can trace their lineage. While most people know by now the mural is actually a not-so-secret entrance, the drinks remain the top selling point. Sit at the bar for a fine view and the chance to maybe pick up a few drops of knowledge so you can drink better at home.
26. Italian beef and Italian ice on Taylor St
There are many places to enjoy the glorious beauty of the Italian beef sandwich in Chicago, but only one is the original Al’s Beef on Taylor St. Paired with an Italian ice from the summer walk-up stand Mario’s across the street, it’s an experience that’s just about as Chicago as it gets.
Sure, you could kayak the Chicago River, which is cool and all, but the new craze in town is stand-up paddleboarding, which you can get into by visiting Chicago SUP just South of Castaway’s on North Avenue Beach for a variety of adventures, including full moon expeditions and lake crossings from New Buffalo, Michigan, to North Avenue Beach.
This isn't about going out looking to get crazy. It's about starting at 11am on a sunny saturday with a bite to eat and some drinks on your favorite patio. Someone suggests hitting another bar. Sure, why not? Then another. Before you know it you're in full-blown crawl mode, making friends with strangers and meticulously developing juke box sets at some dive bar you stumbled into. There's something particularly exhilarating about doing it on a Sunday... at least until Monday hits.
29. Rainbow Cone
Not only does Rainbow Cone make awesome ice cream and yogurt, it’s been doing it since 1926.
For some this has become an annual tradition, for others it’s too much, but you have to push yourself to the limit at least one year, so it might as well be the year there’s a damn Beatle headlining! That still sounds kind of weird, right?
No, you won’t find Elvis’s grave here. Instead, Graceland Cemetery serves as the burial ground for many of Chicago’s most influential residents including Mies van der Rohe, George Pullman, Louis Sullivan, and Daniel Burnham. The monuments and tombs are a sight to see... and cheaper than a pilgrimage to Jim Morrison’s grave in France.
Of course you’ve had a Chicago-style dog more times than Walter Payton has juked out a linebacker. But this classic South Side stand swaps that wiener out for a tamale and covers it in chili -- creating a tasty, messy Frankenstein of a sandwich that must be experienced to be believed.
The authentic way to prepare Chicago-style barbecue is with an aquarium smoker, and no one does it better than Lem’s Bar-B-Q.
Cubs fans can talk about tradition all they want, but this Sox hangout in Bridgeport has the distinction of being the oldest bar in town (since 1881). Stop in before a game for some butt steak, free parking (with dinner), and a cold brew with plenty of colorful characters.
Is jumping into an ice-covered lake in your skivvies kind of insane? Yeah, but isn’t living here during winter kind of insane, too?
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Raf still needs to cross off several items from his personal Chicago bucket list, including riding around town on a tandem bike with Joakim Noah. Follow him @RafFoSho.
Jay Gentile is Thrillist's Chicago Editor and he is still looking to bum a ride on your sailboat to Mackinac Island. Follow him @ThrillistChi.