Chicago’s Best End-of-Summer Dates

Chicagoans have been kissed by a delightful summer this year, with moderate humidity, plenty of sunshine, and just a few showers here and there. Before my favorite season arrives in a month or so (insert Kanye “I’mma let you finish” reference), squeeze every last drop of what the city has to offer with these best summer date ideas.

  • Buy a 24-hour Divvy pass ($9.95 + tax) and ride along Lake Shore Drive. If you’re just biking along the lakeshore, helmets aren’t needed. Buy sandwiches to go and pack with drinks (avoid glass, pls) and a blanket for a picnic by the “Theater by the Lake” station along the water. Bonus points if you cue up this song on your iPhone or handy mini Bluetooth speaker.
  • Kayak the Chicago River, or if you’re more of a lazy water baby, corral a few couples and share a rental of an electric boat. Check Groupon first.
  • If you have a car, drive to the Chicago Botanic Garden and saunter through the gorgeous, immense grounds. Fyi – admission is free, but parking is steep. Make the painful moment quicker by having cash on hand.
  • Stroll through Logan Square on a Sunday. Take the Blue Line to the California stop, and walk northwest along Milwaukee Avenue to see the restaurants, bars, and boutiques that have sprouted in less time than it takes to train for a marathon. Peruse the farmer’s market (10 a.m. to 3 p.m.; get extra smooches with a bouquet of local wildflowers), then have brunch at Jam, Reno, Longman & Eagle, or my personal fave, Lula Café. Finally, people-watch on the grass at the historic Illinois Centennial Monument.
  • Spend a Saturday shopping along Milwaukee and Damen avenues in Wicker Park. Starting at 6 p.m. Saturdays and 1 p.m. Sundays, have a scenic pre-dinner drink at the Mad Men-reminiscent Robey rooftop Up & Up (entrance is on the North Ave. side). If the wait at Big Star is too long (when isn’t it?) try their booze-free adjacent patio, or people-watch from bar stools along the window at retro Dove’s Luncheonette. If the temperature is 80 degrees or higher at the time, snag a free matcha ice cream dessert at Kizuki Ramen & Izakaya.

    The view from The Robey’s rooftop Up and Up bar.

Have you tried any of these date ideas? Have other end-of-summer recommendations? Let us know in the comments, or tweet us at @nextdatechicago, and you’ll get a shout out.


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