8 Best Places to Visit On a Summer Vacation in Chicagoon June 22, 2021 at 12:56 am

You’re vaccinated, you’ve got a significant other to do things with, and Chicago is open for the summer season— so now what are you going to do? There are so many great ways to have fun with a friend here in the city; here are just a few suggestions to resurrect Date Night with the perfect summer vacation.

1551 W North Ave, Chicago IL 60622

Experience Patio Season as it was meant to be experienced with a great view of the city and the perfect cocktail. This newer rooftop spot in Wicker Park is situated at the top of Hyatt Place Chicago/Wicker Park, giving you the best vantage point from which to appreciate the skyline with your boo.


2444 N Elston Ave, Chicago, IL 60647


Located at 2444 N Elston Ave, Chicago, IL 60647, The Hotel at Midtown is perhaps the finest boutique hotel in the entire city to visit in the summer. But it’s so much more to that. Attached to the Midtown Athletic Club, a stay at The Hotel at Midtown gives you access to a world-class fitness facility, a brunch restaurant, indoor and outdoor pools, tennis courts, and a spa that is to die for. If you’re looking for hotels to visit for your vacation in Chicago, The Hotel at Midtown is truly a perfect blend of luxury and wellness. Enjoy the indulgence without having to stay directly in the heart of The Loop.

700 E Grand Ave, Chicago IL 60611

With food, music, and other attractions, it’s no surprise that Navy Pier is one of Chicago’s top destinations. Even if you’re a Chicago native who’s had all the deep-dish pizza and ferris wheel rides they can stand, the summertime fireworks are always a great opportunity to get outside with your honey and gaze at the night sky.

222 W Merchandise Mart Plaza, Ste 470, Chicago IL 60654

This huge light display on the facade of the old Merchandise Mart building is often accompanied by music, and features work by world-renowned artists. What better way to enjoy the summer nights on your vacation in Chicago than to see some local art in the fresh air?

300 N Central Park Ave, Chicago IL 60624

With thousands of plants on display in eight different indoor gardens, Garfield Park Conservatory is an oasis of green within the urban landscape. Make a reservation for you and your friend to take a minute and smell the roses.

This 1.25-mile walk includes some of the city’s best dining, public art, outdoor activities, and more. If you are taking a vacation in Chicago, we recommend checking out the Chicago Architecture Center. Grab some lunch at one of the Riverwalk’s many restaurants, and even try your hand at urban kayaking!

220 E Chicago Ave, Chicago IL 60611

June through August, you can catch live music at the Museum of Contemporary Art every Tuesday at 5:30p.m. No more date nights watching music livestreams on a screen!

Photo by Sawyer Bengtson on Unsplash

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