Need Plans For This Weekend? Here's What To Do In Chicago

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If you feel like summer is passing you by, don’t freak out too much. Yes, July is over halfway gone, but you still have five weekends before Labor Day. Of course, one of the best — and hardest — parts about living in Chicago is that many of the best summer activities roll around once a year. Feeling the panic come back again? We’ve rounded up the best things to do in Chicago this weekend, from yoga with your pup to cocktails and tacos galore. Oh, and 29Rooms, our expansive, immersive experience, is back to the Windy City for a second year. In other words, your weekend is going to rock.

Catch A Pitchfork Aftershow

A three-day pass to the annual Pitchfork Music Festival isn’t cheap. But if you want to get a dose of indie cool for less, grab a ticket to one of the festival’s many aftershows located at various venues around Chicago. Tickets start at under $20 for many shows. If the bands and artists don’t ring any bells (unlike Pitchfork headliners HAIM or Robyn), many soon will. Our top pick is Snail Mail, aka 20-year-old wunderkid Lindsey Jordan, whose addictive love songs will become the new soundtrack to your late summer angst.

Doga at Sheffield Street Festival

This is the 51st annual Sheffield Street Festival, but we bet half a century ago they didn’t have yoga, much less dog yoga, aka Doga. Designed for dogs and their humans, the hour-long all-levels Vinyasa class is perhaps the calmest way we could imagine to kick off a Saturday. You can reserve a mat for $15, which is donated to the Sheffield Neighborhood Association. If you want to hang around until the rest of the festival kicks off at noon, grab brunch at nearby Homeslice afterwards to kill time.


29Rooms is kicking off its seven city tour in Chicago this week, with 29 immersive, unique experiences exploring this year’s theme, “Expand Your Reality.” You’ll find local artists, an all-day dance party, and more. This year, it’s in the Skylight Board of Trade building, turning the former trading floor into something totally unique. Fan favorite rooms from last year from collaborators like the ACLU, Kali Uchis, and The Hoodwitch will also be returning. Get your tickets here, and get ready to get surreal.

Dinner at Summer House Santa Monica

Yes, the Chicago beaches are fun, but if you’re craving ocean instead of lake, you can at least get the vibes of the west coast at Summer House Santa Monica. The seasonally-inspired spot is open year-round, but what better time to drop by than when you can get a watermelon cocktail or pasta made with local tomatoes? The airy, sunny dining area has the added benefit of having a glass roof that will make you feel like you’re dining al fresco while still availing yourself to A/C on days when it’s reaching the 90s.

Drinks and a Dip On The Robey Hotel Rooftop

Hotel pools are a great way to cool down, but are usually reserved for hotel guests. That is, unless you head to the Robey Hotel’s rooftop, where you can get city skyline views and splash around without a reservation. Of course, you’ll also want to take advantage of their food and drink offerings. If you show up at 11 a.m. when they open, you can grab a smoothie. Come in the evening and opt for a frozen cocktail and fries while you dry off.

Get A Sugar Rush At Milk Bar’s Pop-Up

Another NYC institution that has taken to the road, Milk Bar’s All You Can Treat tour is stopping by Big Star in Wicker Park this weekend. Try the cookies, cake truffles, and cereal milk soft serve that have become beloved by sugar freaks worldwide. There will also be merch for sale if you need to find ways to show your Milk Bar love the other 364 days of the year.

Tacos y Tamales Festival

Based on traditional open-air markets in Central America called tianguis, the Tacos y Tamales Festival puts special focus on, you guessed it, tacos and tamales. Admission to the street festival is free, though there is a $5 suggested donation to the Frida Kahlo Community Organization. Modelo sponsors the event, so you can grab a beer or michelada at their beer garden to cool off. Need something stiffer? There are a few tequila tastings throughout the weekend. For $39, you get 15 samples, along with some much-needed snacks.

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