Chicago Bucket List

Although I have lived in Chicago for more than five years, there are still a lot of things I haven’t gotten around to doing in the city.  As the prospect of graduation becomes slightly less nebulous, I’ve started to realize that I may not be here for too much longer.  So I’m making a bucket list of all of the Chicago activities that I’ve been postponing indefinitely and want to do before I leave.

Chicago Bucket List

1. Go to the Shedd Aquarium

I’ve heard a lot about the aquarium, and I keep seeing ads for it around the city, but I’ve never actually made it there.  The only time I attempted to go, there was a two hour line, and I decided I’d rather lay on the couch.

2. See all of the galleries at the Art Institute of Chicago

The student membership rate at the Art Institute is quite reasonable, but despite having been a member for two years, I still haven’t seen all of the exhibits there.  With winter making being outside rather unpleasant, the next few months might be a good time to go explore the Art Institute.

3. Go to the Planetarium

As with the aquarium, I keep meaning to go to the planetarium, but I haven’t made it there yet.  This is another good indoor activity during the winter.

4. Spend a day at the Field Museum

I’ve been to the Field Museum a couple of times already, but I’ve only seen a fraction of the museum.  It’s definitely worth a full day’s visit.

5. Go to Lincoln Park Zoo

I’ve been to the Lincoln Park Zoo, the oldest zoo in the country, various times, but I haven’t actually seen the whole thing.  I think it would be a nice afternoon outing when the weather gets warmer.

6. Bike the Lakeshore Trail

I don’t actually own a bike, nor do I really like biking, so I might amend this to running the Lakeshore Trail.  The trail is an easy way to spend time outdoors in Chicago when the weather is nice, and I would like to explore the whole thing.

7. Go to a concert at Millennium Park

During the summer, there are free concerts nearly every day at Millennium Park.  I went to a couple of these back when I first moved to Chicago, but I haven’t been back since.  This is a perfect summer activity for Chicago.

8. Attend a CSO concert at the Ravinia Music Festival

The Ravinia Music Festival is an outdoor performance venue with lots of concerts during the summer, including many CSO performances.  I’d like to go this summer with a picnic and sit on the lawn to listen to the concert.

9. Go to the Museum of Science and Industry

I’ve heard lots of good things about this museum, so I’d like to check it out!

10. Attend a performance of the Chicago Symphony Orchestra

I’ve been to one performance of the Chicago Symphony Orchestra, featuring one of my all-time favorite pieces of music, Mussorgsky’s Pictures at an Exhibition, and it was excellent, so I’m hoping to go back soon.

11. Attend a season at the Chicago Lyric Opera

The student tickets for the Chicago Lyric Opera are a steal, especially compared to regularly priced tickets.  I’m aiming to making to all of the operas in a season, a feat I haven’t managed yet.

12. See the Improv Shakespeare Company perform

The Improv Shakespeare Company is just one of the myriad of comedy options in Chicago, and they do a fantastic job.  I’d like to make it to another one of their performances and spend a couple of hours laughing until my stomach hurts.

13. See a comedy show at The Second City

I’m almost embarrassed to admit that I’ve never been to The Second City, the city’s premier comedy club.  With many famous alumni such as Steve Carell and Stephen Colbert, I can’t leave without seeing at least one show there.

14. Go to a comedy festival

There are a number of comedy festivals going on in northern Chicago throughout the year.  I’ve seen ads for them all over the city, and I think it would be fun to check one out.

15. See an off-Broadway show in the theater district

Until very recently, I didn’t even know that Chicago had a theater district.  It does exist though, and there are many touring shows that pass through.  I’ve seen a couple shows here, including The Book of Mormon and Wicked, but there are several more that I still want to see.

16. Go to a cider bar

I’ve heard rumors of a cider bar opening up in Wicker Park, and as a lover of hard cider, I’m going to have to seek this place out.

17. See a show at the Steppenwolf Theater

One of the train lines passes by the Steppenwolf Theater, and I’m curious about what kinds of shows they have there, just based on the name.  I want to show up one day and see what’s going on there.

18. Go to the Orchid Festival at the Chicago Botanic Garden

The Orchid Festival at the botanic garden is supposed to be magnificent.  It happens every spring, and hopefully, I can make there this year.

19. Have drinks in the Signature Room at the top of the Hancock Tower

There is a terrific view of the Navy Pier fireworks from the Signature Room, especially from the women’s bathroom (I won’t tell you how I know that).  One of these days, I’m going to go back and actually have a drink while looking out at the city instead of just camping out in the bathroom.

20. See the fireworks at Navy Pier

I’ve been to the Fourth of July fireworks once and the weekly summer fireworks a couple of times, but it’s been several years since I actually watched fireworks from Navy Pier, so that’s on my to-do list for the summer.

21. Go to the Chicago History Museum

My friends got married at the Chicago History Museum last fall, and that was the first time I’d heard of the museum.  From the brief glimpse I had of it, it seems like a fascinating place to learn about the city.

22. Visit one of the fine dining vegetarian restaurants in Chicago

There are a number of fine dining experiences in Chicago, including Alinea and Next, but there are also some that do vegetarian/vegan food.  I’m saving up money to try one of these out. And if you have suggestions, they’d be most welcome!

23. Eat Mexican food in Pilsen

Pilsen is the neighborhood that is supposed to have the best Mexican food in Chicago.  I’ve had some great Mexican food in other parts of the city, so I’m really excited to see what Pilsen has to offer.

24. Go dancing at the Summer Dance Festival in Grant Park

The free dance lessons at the Summer Dance Festival are always a lot of fun.  I haven’t been in the past couple of years, but this summer, I’m going to take full advantage of the lessons to learn different styles of dance.

25. Get my picture on the wall of fame at Pho’s Hot and Spicy

Pho’s Hot and Spicy is a small hole-in-the-wall Thai restaurant in Lakeview.  They have absurdly spicy food there, and if you eat something with a certain level of spiciness, you get your picture on the wall.  I’ve eaten capsaicin extract before, but I’m not sure I can handle the spice there.

26. Go apple picking

Since I didn’t make it out to go apple picking last fall, I’m putting this back on my bucket list.  I’ve heard good things about Midwestern apple orchards and I really want to check them out for myself.

27. Have afternoon tea in downtown Chicago

There are all kinds of fancy afternoon tea options in downtown Chicago.  They can be rather pricey, but I’m going to try to find one that’s reasonably priced and vegetarian friendly.

28. Run a half marathon

This is not so much related to being in Chicago as it is to my fitness goals for the next couple of years.  Hopefully, I’ll be able to check this one off the list this year.

29. Have specialty donuts

There are a lot of donut shops in Chicago, as the city seems to have a bit of an obsession with donuts.  I’ve yet to try the more popular ones like Glazed & Infused or The Doughnut Vault, so I need to remedy that soon.

30. Try all of the deep dish pizza places in the city

I don’t know if I can track down every place in Chicago that serves Chicago-style deep dish pizza, but I’m certainly going to try!

31. Attend a Chicago Cubs baseball game

Wrigley Field feels like an old neighborhood ballpark, and I want to go experience it again on a hot summer day, even though the Cubs are a terrible team.

32. Attend a Chicago White Sox baseball game

The White Sox are definitely the Chicago team with the better track record of winning games.  Tickets are pretty cheap, and the ballpark is nice, though it doesn’t have the nostalgia of Wrigley Field.

33. Go to a neighborhood street festival

I walk by street festivals all the time in the summer, but I rarely stop to see what’s going on.  This year, I’m going to try to make it to at least one street festival.

34. Ride the ferris wheel at Navy Pier

A very touristy thing to do, I’ve never managed to ride the ferris wheel at Navy Pier.  It seems like the view would be nice, so I might give it a go.

35. See a play at the Chicago Shakespeare Theater

The Chicago Shakespeare Theater has cheap student tickets, so there’s no reason for me not to go.  Maybe I’ll try to make it to Pericles this year.

36. Go to a rooftop bar

Chicago is full of rooftop bars, but I’m not sure I’ve actually been to one.  I plan to fix this as soon as it’s warm enough to be outside.

37. Go on a cupcake crawl

Although the specialty cupcake storm is dying out, there are still lots of cupcake stores around the city, so I’d like to spend a Saturday doing a cupcake crawl and sampling different types of cupcakes.  I just hope I don’t get diabetes!

38. See the Chicago River being dyed green for St. Patrick’s Day

It’s usually pretty cold when the Chicago River is dyed green for St. Patrick’s Day, so I’ve always been too lazy to go watch.  Before I leave Chicago though, I have to see it at least once.

39. Have brunch at Wildberry

Wildberry is a brunch/lunch place right next to Millennium Park.  It’s extremely popular, with waits often being longer than an hour, but with good reason.  I went there over a year ago, and I still dream about it.

40. Spend a day at the Brookfield Zoo

I’ve heard great things about the Brookfield Zoo in the Chicago suburbs, and I’d like to go see it sometime.  It is much larger than the Lincoln Park Zoo with an extensive collection of animals.

41. Eat chocolate lava cake at The Grand Lux Cafe

The Grand Lux Cafe is in the heart of downtown Chicago on Michigan Avenue.  The chocolate lava cake, a chocolate cake with a melted chocolate interior, is one of their specialty desserts, and it is fabulous.  I can’t think of a better way to spend an evening than eating cake and sitting at one of the window tables overlooking the Magnificent Mile.

42. Listen to free jazz at the Museum of Contemporary Art

Despite living within walking distance of the Museum of Contemporary Art for two years, I never actually went inside.  They  have free jazz performances on Tuesdays during the summer, so I’ve resolved to go see the museum and enjoy some jazz.

43. Walk the Riverwalk

The path along the Chicago River is very pleasant for a walk during summer evenings.  I love meandering down the path and admiring the city when it’s all lit up at night.

44. Go to Green Mill

Formerly the hangout of Al Capone, this lounge seems like an intriguing place to spend an evening people-watching and listening to jazz.

45. Play beach volleyball on North Avenue Beach

North Avenue Beach has lots of beach volleyball courts set up during the summer for recreational leagues and casual play.  I’m not much of an athlete, but I have an idyllic image of playing volleyball in the warm sand as the sun sets over Chicago.

46. Go on a bar crawl

There are bar crawls happening all the time in the city, but I’ve never been to one.  Before I move, I’m going to take part in my first bar crawl.

47. Go to the Gay Pride parade

The Pride parade seems like a colorful and fun time, and I’m curious to see it sometime.  Everyone I know who’s been has really enjoyed it.

48. Attend Wait Wait Don’t Tell Me

For fans of NPR, Wait Wait Don’t Tell Me needs no introduction (if you haven’t heard of it, you should give it a listen).  Having grown up listening to NPR as a kid, there is no way I can leave Chicago without seeing a taping of the show.

49. Do a Frank Lloyd Wright architectural tour in Oak Park

There are a number of houses and buildings designed by Frank Lloyd Wright in the Chicago suburbs, and I recently discovered that there is a guided architecture tour dedicated to seeing them.  I don’t know a lot about architecture, but it would be interesting to learn more on one of these tours.

50. Do a Chicago Architectural Boat Tour

I’ve been on a couple of Chicago boat tours, and I really enjoyed them.  I want to do another as a farewell cruise before I leave Chicago.  What better way is there to say goodbye?

Any other suggestions for my Chicago Bucket List?

3 responses to “Chicago Bucket List

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