My Ultimate To-Do List for Summer in Chicago

This week marks exactly 10 years since I loaded up a moving van in Minneapolis and drove seven hours south to make a new home in Chicago.  In the decade that I’ve lived here, a lot has changed but one of the constants is that summer is undoubtedly the best time of year in the city – and not just because of the weather (and, okay, sometimes in spite of the weather).

Nonetheless, I feel like I haven’t taken full advantage of all that Chicago summers have to offer. So at the suggestion of my friend Megan, and with the help of many others on Facebook, I came up with my ultimate to-do list for Summer 2011:

1.  Expand my musical horizons in Millennium Park. There is no shortage of free (yay for free!) music to enjoy in Millennium Park.  I can discover cutting-edge indie rock, pop bands and rock veterans on New Music Mondays.  Or I can scope out Music Without Borders, which “brings the best global sounds to Chicago.” Or I can return to Chicago’s roots and take in the World Class Jazz series, featuring some of Chicago’s best jazz musicians.  So many options!


2.  Catch a movie under the stars. I love the concept of Movies in the Park – check out a classic movie on the big screen under the stars with good friends, some snacks and a bottle of wine.  With a long list of movies to choose from at parks across the city, there’s something for everyone.  Even better?  It’s free!  On my list:  Dirty Dancing, Ferris Bueller’s Day Off, Grease, the Wizard of Oz, West Side Story and Sixteen Candles.

3.  Volunteer for the Rock’n’Roll Chicago Half Marathon. I have run many races here but have never volunteered at one, so I decided it’s about time to give back.  I’ve signed up to work at the start/finish line at the Rock’n’Roll Half on August 14.

4.  See Eminem perform at Lollapalooza. I went to Lolla the first three years it was in Chicago.  As someone who isn’t much into the indie music scene, I went more for the atmosphere, the people-watching and the big name acts – the Killers, Pearl Jam, Kanye West and the Red Hot Chili Peppers.  My main goal this year: to see Eminem. I know he can be controversial, but I think his lyrics are absolute genius and “Lose Yourself” is one of my favorite all-time songs that inspires me every time I hear it. (any leads to a discounted day pass would be much appreciated – they’re not cheap!)

5.  Take a Chicago Photography Walk. I recently took a beginner photography class and could not believe how much I learned.  With a new camera, I am hoping to start applying my new knowledge both here in Chicago and when I travel.  Chicago Photography Walk provides the perfect opportunity for me to explore Chicago in-depth and learn more about taking great photos at the same time.

6.  Go on a date at Navy Pier.  I may be the only non-tourist in Chicago who actually likes Navy Pier, which is probably why I only go there when people have visit from out of town.  But there is something about Navy Pier that makes me think it would be a great date destination, in a cheesy, romantic, high school kind of way.  I’m picturing dinner at Harry Caray’s, strolling along sharing a scoop of Ben & Jerry’s or  a bag of Garrett’s popcorn, drinks in the Beer Garden while jamming to some live music and ooh-ing and aah-ing while watching the fireworks over the pier.

Navy Pier

7.  Get my groove on at Chicago SummerDance. Starting in July, Chicago SummerDance is the largest annual outdoor dance series in the country.  Each night of the series offers an introductory one-hour dance lesson followed by 2 hours of live music and dancing in the Spirit of Music Garden in Grant Park.  And like Movies in the Park, Chicago SummerDance is totally free! While I have never professed to be a good dancer, I do love to dance, so this is something I have to try.

8.  Mix up my running routine. I have been meaning to participate in Fleet Feet Sports’ Fun Runs for about three years now.  Leaving every Monday and Wednesday from the Lincoln Square location at 6:30 p.m. and going 3-6 miles, they would be a great way to break up my normal running routine.

9.  Play mini-golf at the Green at Grant Park. Mini-golf was one of my favorite summer activities when I was in high school.  I suspect playing some putt-putt in Grant Park will beat out the 9-hole course on the side of Highway 96 that I frequented as a teenager.

10.  Enjoy a concert at Jammin’ at the Zoo. I’ve missed the likes of Everclear and Sister Hazel playing at Lincoln Park Zoo in the past, much to my dismay.  They haven’t announced this summer’s schedule yet, but I promise, I will make it to see at least one previously great band that likely enjoyed its heyday in the mid-90s.

11.  Explore the Farmer’s Markets. I am somewhat embarrassed to admit that I have never been to a farmer’s market in Chicago. So I am going to remedy that this summer.  While the Green City Market in Lincoln Park is probably the best known, I’ve also discovered that I’ve got the Lincoln Square Evening Market and the Northcenter Market in my own ‘hood.  Looking for a farmer’s market in your area?  Check out this list.

12.  Try 10 new outdoor drinking locales. Ok, this isn’t anything new, but I tend to stick with the familiar.  I find a bar, I like it, and I go back there – a lot.  So when I read that there are over 50 new rooftops, beer gardens and sidewalk cafes opening this summer, I decided I need to make a concerted effort to branch out.  Sampling all 50 would be a little ambitious, so I’m going with a more reasonable goal of checking out 10, including South Branch (perfect for a Friday happy hour in the Loop), Wolcott’s (just blocks from my house) and Club 162 (great for some pre- or post-Cubs game drinking).

Lake Michigan sunrise

13.  Stay out all night and watch the sun rise over Lake Michigan. While training for the Chicago Marathon last summer, I typically started my Saturday long runs around 5:30 a.m. in order to finish before it got too hot.  On one of these early mornings, I was running down by North Avenue Beach and saw a couple of twenty-somethings frolicking in the water, wearing what were clearly their clothes from the night before.  At that moment, I started thinking how fun it would be to stay out all night and end up at the beach, watching the sun come up over Lake Michigan.

So there you have it – my ultimate to-do list for this summer, and what I personally think is a great list of activities to try in Chicago whether you’ve lived here a decade or are just passing through for a few days.  Am I missing anything that you highly recommend?

Of course, it would be way more fun to have some partners in crime as I make my way through my list – if you’re interested in joining me for any of the above, let me know!

Photos: La Sequencia, Ed Goodwin, John Picken

15 thoughts on “My Ultimate To-Do List for Summer in Chicago”

  1. Cool list. I went to a drive-in last summer somewhere in the suburbs, it was fun. I’ve never heard of mini golf in Grant Park but the burbs have some superior mini golf action. And I always go to as many free festivals as possible – I figure, it’s our tax money that’s going to fund most of these!

  2. Sushi Mura on Southport. We left Chicago 5 years ago and I still dream about the crunch tuna roll. It was the first restaurant I ever really got into raw fish sushi (stuck to veggie rolls before that I am sad to admit). Mama-san and Papa-san are a hoot too. Papa-san will do sake bombs with whoever orders them. He gets more drunk as the night goes on and mama-san gives him dirty looks. Have an awesome summer in Chicago! One of these days we will get back there.

  3. I love Chicago, and have been there probably 15-20 times since it so close to STL, and think you have a great list here. One bit of summer fun that I enjoy here and I bet you can do up there is find an old school Drive-In movie theater … it truly is one of the most “summery” and “Americana” type things you can do!

    1. Thanks Scott! Love the drive-in suggestion – used to love those in high school (lived in Minnesota then). Will have to do some research and see if we have any here – thinking it might require a trip to the ‘burbs…

      Let me know if you make it up here at all this summer – would be great to meet in person!

    1. Yay! Between this and the guest post I did for you guys, you should be all set when you come through town! Still bummed I’ll miss you!

  4. Ralph DePasquale

    Great list! I have a few more things for you too,.. if you’re still interested?!? Didn’t you do number 13 after our show?? lol. If not, I have a great way to check that one off and do something very cool too. Do the McDonald’s late ride with me! I am getting a few people to do it this year. Mid-July and fun ride through parts of the city you would likely never ride your bike through and it all culminates with a McD’s breakfast at Buckingham Fountain to watch the sun come up!!

    Two more things: 1. Adler after Dark – Some of the best views of the city at night and cool things to do inside as well. I am member,..we can talk. 2. Sail in one of the beer can races. Can talk about that too. I would love to do some of the things on your list that I haven’t done.


    1. LOL, I did get to see the sunrise after our show, but only from the Golden Nugget! Definitely like the idea of the late ride – just need a bike!

  5. Nice! Chicago in the summer really can’t be beat. I did Summer Dance last year and LOVED it. So fun…and very international. I even met some Couchsurfers there!
    I used to do Yoga at sunrise @ No Ave Beach when that outdoor gym was still there. LOVED that. I have to check out the people behind Photo Walk and maybe do a story on them. I like it!!

    1. Thanks! Very excited to try SummerDance – everyone I know who’s done it has had a blast. Hoping to try the Photo Walk as soon as it warms up a bit – will let you know how it goes!

  6. Great list! I love the farmers markets, especially Green City. I also want to play mini golf in Grant Park, go to jammin at the zoo and see one of the movies under the stars. Also on my list: the Horse exhibit at the Field Museum, finally going to the beach (yep, nearly 5 years here and I have never been!), and riding the Navy Pier Ferris Wheel.

    1. Thanks! But wait, you’ve never been to the beach here?!?! That needs to change! 🙂

  7. I meant to go to yoga at Millennium Park last summer so I’m going to try again this year if they’re offering it. The farmer’s market in Logan isn’t huge but it’s a nice scene with people selling stuff out on the boulevard and sitting in the grass.

  8. This is a great list! I make my summer to-do list every year, and I may be stealing some of your ideas. I’ve never heard of the Photography Walk! How cool!

    1. Thanks! Steal whatever you like – and let me know if you want to join me for any of these! I may try to volunteer at Retro on Roscoe too (you suggested that one, right?) but it’s the same weekend as Lolla…Eminem has priority! 🙂

Comments are closed.

Scroll to Top