Labor Day Weekend in Chicago

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I struggle with Labor Day weekend. I want to soak in every last drop of summer but if we’re being honest, I am also ready for college football, chili and leather boots. In the spirit of not denying ourselves our respective college season openers and making the most of summer specific activities, here’s a list of both to help make planning for the long weekend less of a challenge.

Chicago Jazz Fest: Pack a picnic and head to Millennium Park for jazz with a side of skyline. Here are four bands you have to see.

Headquarters River North: This Lakeview favorite brings their huge craft beer selection and arcade games to River North. Opens today and in case beer and pinball isn’t enough for you, this location is going to have food.

Magnificent Mile Women’s Half Marathon & 5k: Ladies, if you’ve been hitting the pavement all summer, do a victory lap by running the first ever race to hit the Mag Mile. Registration for both the half and 5k looks like it’s still open.

Critical Mass Ride: A few weeks ago, we were test riding bikes and I fell off mine at a stop sign and yelled “I DON’T WANT TO RIDE BIKES!” as I got up so this is a suggestion for you, not me. But if you are a biker of the pedal-y sort, head to Daley Plaza on Friday at 5:30 for this free ride through the city’s streets with a few thousand of your biker friends.

Fireworks Cruise: Water. Skyline. Fireworks. Enough said.

College Football Bars: We live in a city with a bar for there is. Here’s a complete list of where to see your team on college game days. (And here’s the Spartan Fight Song for good measure.)

Elle on the River: one last shot at tacos and punch al fresco. This has been one of my favorite spots this summer and the only thing better than their fish taco on chickpea flatbread is the views of the river.

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Summer Send-Off

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Last night, we attended a cook-out at the home of friends in Lincoln Park.  We’ve spent several Memorial/Labor Days with them and I must say, I’m a sucker for the rooftop element to this gathering.

This Labor Day isn’t messing around with its “Hey, summer’s over!” message so it was an evening for sweaters over dresses and shorts, an evening that forced our hosts to bring out the patio heater when blankets just couldn’t cut it.  But it was also a night for burgers on the grill, 312, Molly’s Cupcakes and Garrett’s Popcorn.


(Note: Ryan and I were craving Garrett’s yesterday so instead of buying it for ourselves, we grabbed a bag to bring as a host gift.  It was a HUGE hit- after sharing a few handfuls with us, our hosts tucked it away to have for themselves today.  So, even if you live in Chicago, Garrett’s is a clutch host gift.)

Last night was the perfect send-off to summer- one last hurrah.  But if we’re being honest, I’m totally eyeing the sweater section of my closet and excited for the cool crisp days ahead.