The Perfect Chicago Summer Week

The Perfect Chicago Summer Week

There is no place like Chicago in the summertime (when it’s actually warm, that is).

With at least one festival in most Chicago neighborhoods, five beach hot spots (North Avenue Beach, Oak Street Beach, Edgewater Beach, Foster Beach and Montrose Beach), and destination rooftops, Chicago summers are a time to explore, get cultured, and maybe get a tan to pair with your white pants.

Relax, explore, move, and enjoy your perfect Chicago summer week.

Sunday: Brunch + BEACH

Enjoy brunch with friends and then go to the beach. Take one of your summer reading books, and if you dare, take a dip in Lake Michigan. If you feel like playing more than lounging, join the fun with beach volleyball (new season starts in August 2015) at North Avenue Beach, tennis at various tennis courts (but I suggest 3700 N. Recreation Drive, right off the Lakefront), or basketball overlooking Foster Beach.

Monday: POETRY

Don’t let a day back to work take away from Chicago’s summer sun. Weeds (1555 N Dayton St.) has an open poetry mic night every Monday. Participate or listen starting at 10 pm.


Go to the Museum of Contemporary Art. Illinois residents enjoy free admission and longer museum hours on Tuesday (year round). During summer, enjoy live jazz music and a picnic in the sculpture garden. There are a la carte options, including adult beverages and a full buffet. In the art museum, stand in a hot air balloon and wait in line to see what is at the end of a dark, winding hall. You can only enter one at a time and experience it in person. Then reflect on what you just saw by sitting on the most comfortable red couch. Feel the shock of one artist’s, Faheem Majeed, use of particle boards to make political and social statements about one of the poorer Chicago neighborhoods, South Shore.

If you feel like being more active in your community, join Open Gov Hack Nights at 1871. Learn about civic issues in Chicago, come up with ideas to make changes, and actually be part of the change.


Life is a beach. Move from your work day flow to the sounds of reggae. Surround yourself with positive vibes on Montrose Beach at The Dock. Live music starts at 7 pm and it gets happening right before 9 pm. It will start to feel like a club as three lines form and beach goers wait 20 minutes to get in. But, no worries, pack a picnic and just lie on the beach and watch the sunset. You will be able to hear the live band behind you.


On the third Thursday of every month Adler Planetarium has Adler After Dark. The party at the museum goes from 6:30 to 10:30 pm.  Look at the night sky inside the dome and find your favorite constellations. Then, go to the Doane Observatory and see them for yourself. Enjoy live music as you explore all of the museum exhibits and galleries. Today, July 16, 2015,  Adler Planetarium is having a special After Dark series due to the newly released photos of Pluto.  For tickets and more information, click here. P.S. Tickets go on sale on the first of the month.

On your average Thursday, go to the iconic, voted #1 art museum in the world, Art Institute. There is free admission for Illinois residents on Thursdays with extended hours (open till 8 pm). Grab an espresso or a bite to eat al fresco in the gardens or experience one of the best Chicago rooftops, Terzo Piano, located in the modern wing of the museum.


Pick a festival and explore a new neighborhood to start your summer weekend. The full list of Chicago summer festivals is available here.

My favorites include Taste of Randolph, Taste of Chicago, Italian Street Festa Italiana, and Taste of Greektown. Basically, Chicago festivals are a great way to experience the food truck lifestyle or dine at one of the nearby restaurants. And, yes, at Taste of Greektown 2013, they did bring a camel for you to ride —in the middle of downtown.

Saturday: YOGA + TIKI

Start your day off with a fun, free fitness class in Millennium Park. McDonald’s sponsors four classes including:

  • Tai Chi: 7 a.m.
  • Yoga: 8 a.m.
  • Pilates: 9 a.m.
  • Zumba: 10 a.m.

Rather than going on vacation, escape to the tropical beats at the speakeasy, Three Dots and a Dash. You will feel like you are on a cruise ship that landed at an exotic island. If your drink comes with a dolphin shaped banana, take it with you and make a new friend on Hubbard Street as you wait in line for Howl at the Moon or Social 25.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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