Healthy Latina Sailing
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The Ultimate Chicago Summer Bucket List

There are a lot of things I love about Chicago, but there’s one thing that tops the list every year. Summer is hands down the number one thing that keeps me sticking around even with the rough winters, high rent, and bad hair days due to excessive winds. The sad thing is, it never sticks around long enough. We usually get at least one month of gorgeous weather when you factor out all the rainy days. Which leaves little time for all of my favorite activities, especially when traveling starts coming in the mix.

Chicago Skyline

For anyone who’s a planner like me, you need a summer bucket list. Check out my favorite spots and activities in the world’s greatest Second City.

Underground Comedy Show – Chicago’s comedy scene boasts some of the greatest like Tina Fey, but paying to visit one of the major comedy clubs is only so fun. There’s a little bit more intrigue to a BYOB and $10 cover that’s sure to make you laugh hysterically. It’s been a while since I laughed until I cried, but I highly recommend the feeling! Pro tip: improv shows are the best ones.

Healthy Latina Sailing

Sailing on Lake Michigan – I had originally purchased a sailing trip for my sister’s bachelorette party, but the weather was too foggy and we weren’t able to use our voucher. I needed to use the trip before it expired, and was able to gain a completely different perspective on the opposite side of the breaker wall. In addition to a fantastic paleo brunch, I was able to spend time with a few of my favorite people and learn more about sailing basics.  Pro tip: sign up for emails from SeaBreeze Charters for the best rates and a really cool captain named Lorenzo.

Montrose Dog Beach

Montrose Dog Beach – You’ll need to borrow someone’s dog for this one, but the Montrose Dog Beach is a magical place. Where else can you go swimming with your pup in an enclosed area and meet so many dog lovers all at once? Pro tip: visit in the early mornings because it’s packed by 10 a.m., always.

Run or Bike on the Lakefront Path – If you love the mix of city grit, nature and a lake that looks like an ocean, you’ve found a home on the lakefront path. It’s mostly a road path, but there are openings to trails and signs along the way that let you know how far you’ve run. Pro tip: you’ll find drinking fountains along the way so you don’t need to worry about water bottles.

Rooftop Bar – If you want to party like a true Chicagoan, you need a great sundress and a signature drink for a rooftop bar. There are so many great ones to choose from, but definitely look for one with a view of the lake or the skyline! A few to check out are: Cindy’s Rooftop, J. Parker, and London House. Pro tip: order a Tito’s with soda and a splash of grapefruit juice for the perfect Paleo and gluten-free cocktail.

Outdoor Brunch – Every city is on a brunch kick now. You can’t go anywhere without people trying to tell you that they have the BEST eggs bennies and their bottomless mimosas are to DIE FOR. Most of the time I don’t fall for this, but there’s something about sunshine that makes me want to brunch so hard, I forget that I have eggs and bacon at home. Pro tip: pick a spot you can bring your dog to.

Wrigley Field Sunset

Cubs Game – I’ve been a Cubs fan since birth, but we’re actually good this year. Which means it’s the perfect time to check out Wrigley Field and learn how to score the game. Or see how you look in a baseball hat. Pro tip: the bleachers are one big party but the covered seats in the 220s are a better view of the first baseline.

Chicago River Walk

Wine Bar on the Chicago River – Chicago just recently poured a ton of money into the Chicago River Walk so you can take a leisurely stroll and marvel at the gorgeous architecture (unbiased opinion here). There’s nothing better than sitting on the steps with your favorite people. Pro tip: stop in at City Winery for a glass of Malbec that will make you wonder why Chicago was ever called the Second City.

And, of course, if you need a tour guide, you know where to find me 🙂

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