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The Chicago Bucket List: 60 Things to Do Before You Die

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Lollapalooza
Lollapalooza | SHEA FLYNN
Lollapalooza | SHEA FLYNN

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.

1. Pull off the Museum Campus Triple Crown

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.

2. Drinks at The Signature Room

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.

3. Grab a dog at the Superdawg drive-in

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.

4. Scalp a ticket for the Wrigley bleachers

So yeah, if you were planning on doing that move this season... might want to wait until late summer, but still, there's no baseball experience quite like it. Pro tip: the ideal day at the bleachers involves you taking a sick day from work. The day after.

5. Experience the Lyric Opera

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.

6. Plan a picnic at Jay Pritzker Pavilion

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

7. Eat one of the world's best meals at Alinea

Hey, we’re all for 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.

ravinia
Carrie Underwood | flickr/Jay Kleeman

8. Take a trip to Ravinia Festival

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.

9. Catch a late-night set at Green Mill

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.

10. Warm up at Garfield Park Conservatory

The lush, massive (and free) tropical room at the Garfield Park Conservatory is a welcome and invitingly humid jungle year-round. The rest of the city? Not so much.

11. Admire the skyline from Montrose Point

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.

12. Dig through the crates at Bob’s Blues & Jazz Mart

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.

13. Take in Pilsen's art scene at 2nd Fridays Gallery Night

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.

14. Get low on a Pedway crawl

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 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.

16. Become a fighter pilot for a day

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.

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?

18. Sit courtside or rinkside at the United Center

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.

19. Do the Chicago Marathon

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.

20. Race your sailboat to Mackinac Island

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?

21. See the inside of a submarine

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.

Deep Dish Pizza
SEAN COOLEY/THRILLIST

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.

23. Speak up at a Second City show

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”.

24. Get tamales from the Tamale Guy

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.

25. Order a cocktail at The Violet Hour

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.

italian beef
sean cooley/thrillist

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.

27. Stand-up paddleboarding on Lake Michigan

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.

28. Lose track of time while day drinking

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.

30. Hit all three days of Lollapalooza

For some, this is an annual tradition. For others, it’s too much to handle, but you need to push yourself to the limit at least one year so it might as well be the year local hero Chance the Rapper is finally headlining.

31. Stroll through Graceland Cemetery

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.

32. Order a Mother-in-Law at Johnny O's

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.

lem's bbq
JIM VONDRUSKA/THRILLIST

33. Sample Chicago-style 'cue at Lem's Bar-B-Q

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.

34. Stop by Schaller's Pump before a Sox game

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.

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’s

Even 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 Museum

Everyone 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.

38. See a game at Wrigley Field

And see if you can land a seat next to the manually operated scoreboard, one of the last of its kind.

39. Take a photo underneath the Bean

It’s pretty much the most touristy thing that can be done in Chicago that should be done at least once, for the sake of posterity.

40. Admire the view of Millennium Park from the CAA

Cindy’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’s

But remember, there are rules.

42. Sing karaoke all night at Alice’s Lounge

Karaoke 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 Chinatown

It’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 Sundae

Margie’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.

Emporium
Emporium | Sean Cooley/Thrillist

45.  Get boozy at a local arcade bar

Emporium, 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.)

46. See a Blue Man Group show

Yeah, it’s touristy. So what?

47. Crush beers with your bros at Castaways

Yes, 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 Science

It’s one of the weirdest things in all of Chicago, and also one of the coolest.

49. Visit all 77 neighborhoods

You 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 Point

This 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 River

The 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 lakefront

Yes, 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 tour

Most 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 Fountain

Take a pilgrimage to a random home near Augusta and Wolcott and admire a 3ft high concrete column of poop in all of its glory.

Devon Food
JIM VONDRUSKA/Thrillist

55. Chow down on Devon

You 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 Pier

We 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 Museum

Sure, 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 Beach

North 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 Box

The 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 Stand

It’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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Jay Gentile is a Thrillist contributor who remains a fan of free things. Follow him@innerviewmag.