Chicago

7 - chicago, where a lot of my family is and my birthplace!

Shaking off the winter weather, Chicago comes alive during the warm summer- and Pride is the perfect and colorful celebration to embrace what this city has to offer. While some staple events remain postponed, Pride in the Park is a live outdoor music festival that is planned for late June, so get ready for some fun with great tunes and good vibes at this welcoming Pride destination.

We all know that Chicago goes all out for St. Patrick’s Day, so it’s no surprise that the entire city comes together for Cinco de Mayo, too. Start with the parade from Little Village that leads to the festivities at Douglas Park with local marching bands, mariachi bands, and beautifully decorated parade floats. Then head to some of the local restaurants for food and drink specials, like a spicy Mexican chocolate cupcake at Sugar Bliss Bakery, or City Winery Riverwalk for drink specials and river views. Grab your partner and let the music take you away with a dance party and salsa lesson at Duet Dance Studios. Now that you’re a salsa dancing pro, it’s time to head out on the water for a proper Cinco de Mayo party cruise on Lake Michigan.

Chicago is magical during the summertime, you see the city come alive beneath sunny days. You can plan a Ferris Bueller's Day Off-themed activity day complete with the breathtaking view from Sears Tower and a visit to the Art Institute of Chicago to check out world-renown art or relax along the sandy beaches of freshwater Lake Michigan. We recommend grabbing a slice of authentic Chicago deep-dish pizza while you're in town to see what all the hype is about.

From doughnuts to hotdogs, the Windy City is a feast for food lovers. Don't miss the drinks at the Aviary.

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