This Weekend in Chicago – Derby Day Edition

2018-05-03T21:02:21-05:00May 3rd, 2018|Life|0 Comments

Looking for something to do in Chicago this weekend?

With two of the biggest drinking holidays being this weekend, and the weather finally cooperating – there seems to be a lot going on! Here are my plans for the weekend, leave a comment if you’ll be attending any of the festivities!


Minus the Bear is playing at the House of Blues! The location is perfect for us, being right next to our apartment, and tickets were only $20! The House of Blues is such a great venue, even if there’s not an “official” show going on. They always have music on the first floor and Sundays they have Gospel Brunch (which I’ve been dying to try!).


From noon until 6p, Joe’s on Weed St. hosts a street festival for the Kentucky Derby! They put up a huge screen to stream the race, and it’s right next to an Off Track Betting where you can place your wagers on a horse. (Personally, I always go for the pink one, and the cutest name – great strategy). Bub City will be there serving food, and you can drink outside! The street festival is free, and if you want to venture into Joe’s on Weed St, it’s a $2 cover. With this year’s Derby Day falling on Cinco de Mayo, they are turning the upstairs of Joe’s into an El Jimador lounge where there will be El Jimador giveaways and Derby drinks, too.

This will be our fourth year attending the Derby Day Street Festival! Now the million dollar question: what to wear?? (still TBD) but I do know I will be busting out these adorable bad boys for the first time this weekend!
I would love to invest in the actual Free People version of these shoes, but that’s just not practical for me! Cute though, right?


Dr. Dog is playing at the Riv! If you’ve never heard of Dr. Dog, you can listen to my favorite album here! They are a very fun and energetic band to watch. Last time they were in town they came on St. Patrick’s Day, and this year it’s Cinco de Mayo, but maybe one day they will come on a lesser-drinking holiday 🙂

Between the Derby Street Party and the concert, I’m hoping to knock back a few margs and tacos to evenly-weight the holidays! I do love the street tacos they make under the bridge next to the Riv… (you should check them out). Anyone have other suggestions?

Runner Up

Reese Witherspoon’s clothing line Draper James has teamed up with Crate and Barrel for a collab of dinnerware and other hosting items. They are kicking off the launch with a party at the Crate and Barrel at 850 W North Ave (yes, a 3 minute walk from the Derby Party), between 1p and 3p, and they’re serving Sprinkles Cupcakes, so… may have to stop by.

What are your weekend plans?

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