The Chicago Bucket List: 60 Things to Do Before You Die
Nailing down a definitive Chicago bucket list is no easy feat, thanks to the seemingly endless amount of options of things to do here. And we should know, seeing as how we did exactly that: Here are 60 essential experiences every Chicagoan must have before they die. Or move to another city, in which case you’re dead to us.
Visiting only one museum in a day is kind of like not getting your Italian beef dipped. So pull up those bootstraps and hit up Shedd Aquarium, Adler Planetarium, and the Field Museum in one go.95th floor lounge and restaurant. Not to mention one of the city's must-poop bathrooms. Pro tip: better hit the ATM first. Chicago-style dog. The classic spot hasn’t changed its recipes since 1948, and remains one of the few drive-ins around town. The day after.
Largely due to the expertly curated Millennium Park Summer Music Series, the Jay Pritzker Pavilion remains the choicest picnic spot in a very picnic-friendly city. It’s also our number one reason to visit the Loop.chowing down on deep dish slices and secret Potbelly offerings, but when one of the 10 best restaurants on the planet is a mere cab ride away, it becomes a place worth cab riding to. At least once in your lifetime.
After selling off the famed Jazz Record Mart last year, 83-year-old owner Bob Koester opened up this new shop in Irving Park that has more records than there are dollars in the Pritzker family’s bank accounts. Well, maybe that’s not true but it’s still definitely worth a visit.
Every second Friday of the month, visitors can check out great local art while strolling through one of Chicago’s most colorful neighborhoods. It’s like the now-defunct First Fridays at the MCA, but cooler because it's in Pilsen.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 bar
Whether you’re shredding your vocal chords to Journey at Hangge- Uppe 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 it’s 4am. No need to end the night though -- you can always head to Jeri’s Grill.
17. Wander through Lincoln Park Zoo
It’s a huge free zoo in the middle of a huge free park. What more do you need to know?
22. Eat that extra slice of deep dishLou'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. 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. 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 StThere 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.
29. Rainbow ConeNot only does Rainbow Cone make awesome ice cream and yogurt, it’s been doing it since 1926. 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.
35. Hike the 606
The 606 elevated walking trail from Bucktown to Humboldt Park is the best thing that’s happened to Chicago in quite some time. It doesn’t hurt that there are dozens of places to eat and drink along the way.
36. Show off your dance moves at Buddy Guy’sEven though Buddy himself typically only plays here in January, stop by any time of year to see some of the finest blues music in the world’s finest blues city.
37. Hit the Chicago Sports MuseumEveryone knows they can find Sue the T-Rex at the Field Museum, but the lesser-known Chicago Sports Museum is a sparkling palace of memorabilia to entertain any local sports geek. Plus, it’s way cheaper than Cubs tickets.
40. Admire the view of Millennium Park from the CAACindy’s rooftop at the newly revamped Chicago Athletic Association continues to be one of the finest places in the city for a cocktail and a view. And then head downstairs to the game room to play bocce on crushed oyster shells.
41. Get mixed up in the turtle racing at Big Joe’sBut remember, there are rules.
42. Sing karaoke all night at Alice’s LoungeKaraoke never really seems like a good idea until around midnight. After 2am, it’s suddenly the best idea ever.
43. Ride the water taxi to ChinatownIt’s one of the coolest urban adventures in Chicago and takes you to some of the best Chinese food in town.
44. Indulge yourself with the World’s Largest SundaeMargie’s Candies has been at it since 1921, serving everyone from Capone to the Rolling Stones, and is still doing its part to fatten up Chicago with the half gallon monster they call the World’s Largest Sundae.
45. Get boozy at a local arcade barEmporium, Headquarters, Replay -- it doesn’t matter. Just grab some change, belly up to the Donkey Kong machine and slip back to 1985. (With craft beer in hand, of course.)
47. Crush beers with your bros at CastawaysYes, there is a definite frat bro vibe here, but where else can you drink on a giant ship docked on North Avenue Beach? Afterwards, hop on a boat to The Playpen to round out the nautical party experience.
48. Get creeped out at the International Museum of Surgical ScienceIt’s one of the weirdest things in all of Chicago, and also one of the coolest.
49. Visit all 77 neighborhoodsYou can’t claim to truly know the “City of Neighborhoods” without venturing beyond your immediate four-block radius. When you do, you might discover that there is actually cool stuff west of Western Ave.
50. Watch the waves crash at Promontory PointThis beautiful little spot in Burnham Park with a killer skyline vista may not be among the city’s most well-known parks, and that’s kind of the whole point of visiting it.
51. Take a boat tour along the RiverThe best way to see the city’s architecture is by boat. And the best way to boat is with booze in hand. Just don’t jump in the water, in case your bucket list also includes a trip to a Chicago jail.
52. Bike the entire length of the lakefrontYes, you could bike the entire 18-mile length of the Chicago lakefront from Ardmore St to 71st. If that’s too much for you, just grab a Divvy and pedal until you feel like stopping.
53. Embark on a brewery tourMost Chicago craft breweries offer free tours. You would be wise to take one. Or just hop on the Chicago Brew Bus and hit up a few places in one day.
54. Admire the glorious Shit FountainTake a pilgrimage to a random home near Augusta and Wolcott and admire a 3ft high concrete column of poop in all of its glory.
55. Chow down on DevonYou can’t truly know Chicago until you’ve taken in the fabled stretch of Indian and Pakistani cuisine along Devon Avenue between California and Ravenswood.
56. Go to Navy PierWe know, we know. It’s just about the worst place in America. But with eateries such as DMK, Porkchop, and Do-Rite, it’s not all bad.
57. Tour the Money MuseumSure, you could make it rain at a strip club, but for a more family friendly experience, head to the Federal Reserve Bank of Chicago and check out its under-the-radar Money Museum to see rare coins and try to detect counterfeit bills.
58. Relax along the shores of Ohio Street BeachNorth Avenue Beach gets all the fame, but this quiet nearby beach has it beat by a mile, especially once they reopen the on-site Caffè Oliva this summer.
59. Catch a show at the Music BoxThe iconic Lakeview movie theater needs to be experienced at least once by any Chicagoan. Come for the show, stay for a drink in the lounge or out in the garden.
60. Eat a 5lb burger and get your name on a plaque at Fatso’s Last StandIt’s called the Jumbo Fatso Challenge, and it requires the human consumption of a ridiculous 5lb burger with a half-pound of fries. Have 911 on speed dial -- after all, there’s a reason this is the last item on our bucket list.
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