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Your Guide to Chicago City Chase...

Before 6 hours of city chasing
...based on the challenges we did (and didn't) complete.

If you did City Chase this year then maybe this list will remind you of the challenges you chose to
take on (assuming there was some overlap). If not, maybe this will inspire you to take it on next year. If you're into the element of surprise (which is part of what makes City Chase so fun) then don't read any further (spoiler alert and all that). I won't be listing all the specifics about any of the challenges so there should still be some mystery around the challenges but this list should definitely give you a leg up if you're just looking to know more before you take this thing on yourself.

For a review of the event as a whole (not a detailed recounting of this year's challenges) check out my Newcity review.

Anyway, here we go. Since we picked up our packets and whatnot at one of the locations earlier in the week we didn't have to arrive at the starting line until just before 10 o'clock when the actual chase kicked off. But we got there around nine and checked out the starting area. Before the race they were giving out plenty of Red Bull and Neutrogena sunscreen and there was an Austrian biker doing all kinds of tricks on his bike. During the pre-race show the announcer said the biker's name about 100 times but I've actually forgotten it.. so now I know why he said the guy's name so many times.

The kickoff of the race involved running around the north part of Grant Park and finding five questions with multiple choice answers. When ordered in the proper way, the five correct letters spelled a word that you had to write down and present to the judges in order to get your clue list so you could start the actual chase. We ended up with the answer BRAUN which got us a list, but in hindsight that doesn't make sense because that's not a word. But if that's not it I'm not sure what the correct answer was. I went back and looked at the clues and there was no W anywhere so the answer wasn't BRAWN. I don't know... Surely Carole Moseley Braun doesn't warrant being the clue to start off a race like this does she?

Anyway, below is the list of challenges we attempted (the ones we actually completed are highlighted in yellow). We spent the first two hours or so deciphering clues, running around without a game plan and basically not completing very much of anything, so we didn't really get into a planning/actionable groove until we were waiting for the Grand bus to take us from #4 to #5 below. From that point on we were moving pretty quickly and had gotten the hang of this whole City Chase thing.

So, here you go. The titles before each challenge are the titles that were given on the clue sheet (some are a bit cryptic but that's the way City Chase rolls):
  1. Careoke - We mistakenly thought this challenge was located at Hubbard and Michigan (as did another team we ran into). It was actually at the CNA Building. Lesson learned. Make sure you know where you're heading before you take off. We burned a lot of time running here from Grant Park and then arguing about where the challenge spot might be.
  2. Roll - Strip bowling at Lucky Strike. We stumbled onto this one when we saw another team entering AMC River East and realized this must be the bowling alley the clue was referencing. Either both teammates needed to bowl a strike (not a spare) or remove an item of clothing each time your teammate failed to get a strike (until you're completely naked). We chickened out on this one after two failed attempts and left. Honestly, when we were here there wasn't much nakedness going on, but there were a TON of participants (around 50) just standing around watching what everyone else was doing (most likely waiting for someone else to get naked). This is a risque challenge but it seems like the nudity aspect gets played up more than it actually occurs.
  3. Skills & Drills - This challenge included a number of beach sports (dribbling, passing and shooting a soccer ball, landing a tennis ball in a specific spot and volleying a tennis ball ten times). We managed most of them fairly well but had to have three tries at the volleying challenge. This was our first completed challenge and we were pretty excited about that.
  4. Cliffhanger - Rappelling down one of the towers at the end of Navy Pier. The line for this one was very very long so we took off after standing in line for a few minutes. A lot of time was wasted getting to (and away from) this challenge. This is probably the most popular of the challenges (for obvious reasons) but not recommended for a team that wants to complete ten challenges (much less place in the competition). Either head here right away (assuming it's in future City Chases, plan to spend several hours here just to get the experience or write it off completely).
  5. Flew the Coop - This challenge involved donning a pair of work gloves, hopping into an animal trailer filled with chickens, catching two of them and putting them into a cage. Both team members had to complete this (separately) within five minutes. Luckily I grew up in the country raising chickens and finished this in around 15 seconds. Brynn took a little longer (it didn't help that I was barking instructions at her the whole time) but we finished with plenty of time to spare.
  6. Wiggle Room - We thought this one was located at Walter Payton Prep School (as did several other teams we saw circling the building and that talked to later on the course) but it was actually at another magnet school. Again, make sure that you KNOW where you're heading before you dedicate time to finding a challenge.
  7. Polar Plunge - This was one of the most fun challenges. As a team we had to shoot five layups and five free throws... from a wheelchair. Each of the ten shots missed resulted in an additional second that both teammates had to be submerged in a metal tub of ice water. We made four of our shots (all layups) and had to stay down for six seconds. That might not sound like much but freezing water is tough to endure. But since it was such a hot day, this one was a blessing in disguise. I would recommend either taking your shoes off beforehand or wearing waterproof socks (Brynn did the former, I did the latter). When you stand up out of a metal tub filled with water all the water falls right onto your feet.
  8. Braveheart - One of the easiest and fastest challenges - each teammate had to lay on the ground and let either a millipede or a cockroach crawl on their face while a snake or a rat crawled under their shirt for sixty seconds. This one was harder to watch than it was to do.
  9. Cup - The line was pretty lengthy for this one (located in a Southport bar) but it moved quickly. The challenge was to compete against another team in a game of beer pong (with no drinking required). We lost to a couple of beer pong pros and had to take three shots (one of soy sauce, one of lemon juice concentrate and one of maple syrup). All three tasted bad but a shot of soy sauce is much worse than it sounds.
  10. Shopping - At a Jewel on Southport we had to complete a very Price is Right-esque challenge, matching at least four of five common items with their exact prices within 45 seconds. We got it on the second try. There was no line for this one.
  11. Special Olympics - This was a pre-race challenge involving raising $40 for Special Olympics Chicago but it could only be redeemed (with proof of the amount you raised) at three challenge locations throughout the city. We redeemed ours at the Jewel.
  12. Brynn the hand-bike master
  13. Paparazzi - This was a near-impossible challenge by our standards. At Rebel Bar & Grill on Clark (near Wrigley Field) teams received a list of ten scavenger hunt items involving the Cubs game and Wrigley Field, seven of which had to be completed to finish the challenge. We passed on this one.
  14. Tour de Hands - This one took a little while to get to (it was on the running trail near Cannon Drive roughly halfway between Fullerton and North) and there was a bit of a wait (around 15 minutes) but it was definitely worth it. Each teammate had to hand-pedal a bike a half mile each in fifteen minutes overall. This was our favorite - it was physically challenging but also a unique experience.
  15. Mission - On North Avenue Beach, just north of Castaways, there were several members of the Marine Corps leading this challenge which involved first swimming/wading a few dozen feet into Lake Michigan (basically enough to get your entire body wet) and then completing some seriously challenging activities in the sand, including pushing giant tires, belly-crawling under a mesh of ribbons and completing twenty pull-ups (as a team). This was the hardest challenge we did (and it didn't help that you first got wet before crawling through sand that then clung to your body) but also one of the most rewarding. For me it was awesome to see Brynn pushing through this one like a little soldier. I already thought she was more hardcore than me but this one confirmed it. I think this challenge invigorated her too because she was leading the way running out of here.
  16. International - This one was a mental challenge more than anything else, involving a number of stations labeled as various countries that you had to run between, following various clues. We stumbled upon it just north of North and State as we were heading to catch a bus at Clark and North to head back downtown for another challenge at Daley Plaza that we were planning for our tenth one. Without this one it's unlikely we would have made it in time to complete ten challenges.
We got to the finish line at 4:10 (the finish line officially closed at 4:30), so I think we were probably one of the last teams to complete ten challenges. Still I think we both felt good about what we accomplished and were just proud to have finished at all.

The after-party at Moe's Cantina was pretty massive. Every chaser got one ticket for a beer (Coors Light) and a mixed drink (with Southern Comfort). The top three teams, best costumes and highest fund-raisers were announced.
Overall, we had a great time over the course of the day (even if we did get in a number of logistical arguments). The biggest thing I would tell future chasers is to not underestimate how difficult this event is. Both Brynn and I exercise quite a bit (typically running about five days a week) and consider ourselves in pretty good shape, but this was a physically exhausting process for us. It may have been less exhausting if we'd spent more time upfront making plans and using the CTA rather than just running everywhere but there were a few challenges that weren't accessible aside from using your feet.

So, to sum everything up... wear sunscreen, wear comfortable shoes and make a plan before you even attempt to tackle your first challenge.


  1. Sounds like a pretty crazy but rewarding day!

  2. Looks like a great after-party. Beer and a cocktail. What a combo!

  3. I've written about this event and seen Chasers running around the city, but I never knew how the day panned out. This was so fun to read. And awesome that you got to hand-pedal a bike, I want to do that! Can't believe you were out running on Sunday after all this on Saturday!

    1. Good to see you on the trail on Sunday! Brynn and I were totally exhausted after City Chase but still had to get our long run in (we did shorten it, though - we were supposed to do 14 but did 9 instead). And then we got rained on for the last 5 miles!

    2. Good to see you too and at last night's BTN party! Can't believe you stayed out to run 5 more miles in the rain--I quit!


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