Food, fun, festivals, drinks, and more this Summer!

Whether you have plans for the summer or not, make sure to check out this non-exhaustive list of fun things to do over the summer! Maybe you can make a night out of these with your friends, family, and/or significant other. This list was kept in mind to satisfy everyone’s leisurely needs.


Now if you’re like me, then you really love food! When I venture out to a new restaurant I always make sure to check reviews and even if they have something I like, I’d be willing to also try something new on their menu. (Side note: For those of you who like to take the occasional guilty pleasure food photo, then these places will guarantee!) Get your food fix with these awesome places:

  • Au Cheval

I mean, come on, it’s voted #1 burger in America! For those of you who haven’t tried it, then I highly recommend getting their double bacon cheeseburger with an egg and a side of fries with your choice of drink. Be sure to arrive with plenty of time to spare, this place doesn’t take reservations and the wait times can be extremely long! During your wait, you can actually check out the next restaurant…

  • Punch Bowl Social

This place is really a one-stop shop. It’s got virtual reality, bowling, bags and table games, karaoke. They also have their famous 360 bar, and really good food and drinks! Enjoy a night there or make a date out of it. This place won’t let you down. (Offers gluten-free and vegetarian options)

  • Pequod’s Pizza

Take a break from Giordano’s or Lou Malnati’s and visit Pequod’s Pizza! Their crust alone is to die for.

  • MingHin Chicago

If you’re looking for exceptional dim sum then this is the place to go! With two locations: Chinatown and the Loop, be sure to visit MingHin for Chinese food cravings. 

  • Del Toro

Located in Pilsen, this place has authentic Mexican food and crafty drinks to occupy your evening out. Make sure you have some time to spare because this place also doesn’t accept reservations, but the wait time isn’t too bad.

  • Tutto Fresco

An underrated Italian restaurant located in the Lakeview area. Good prices, friendly staff, and amazing food! Make sure to give this place a visit.

  • Cafe Iberico

Tapas and paella that is to die for! Affordable prices and amazing food, this place would make for a good date night or just a night out with friends. This place also doesn’t accept reservations if it’s a party of two, but the wait time is never horrible. This place won’t disappoint! 


This is by no means an exhaustive list of places to get a drink in and around the city, but be sure to check out these places, if you haven’t already. Drink responsibly!

  • Off Color Brewing Taproom The Mousetrap

Located in Logan Square, this taproom will be sure to satisfy your craft beer cravings and it’s even bring your own food (BYOF)! Bring some board games to share with friends or you can even take a tour. This place won’t let you down!

  • Roof on theWit

Located on the 27th floor of theWit Hotel, be sure to dress to impress when going to this rather “boujee” bar that also has fun events and small plates for you to enjoy.

  • Hampton Social

Arguably one of the most Instagram-able spots in the city, be sure to brunch it up with your best friends or enjoy some nice drinks and cocktails with whomever you please! #RoseAllDay

  • City Winery

While there are many locations, be sure to check out the location by the Riverwalk during the summer! Enjoy a nice glass of wine and sit inches away from the river, or sit down and enjoy it with a meal. With the expansive wine list (and limited beer list), this place and the views are delightful.

  • The Dec Rooftop Lounge + Bar

Located at the Ritz-Carlton, come here for the sights alone, or enjoy a nice drink with your friends and loved ones!

  • Kaiser Tiger

Check out their beer-garden and enjoy the rooftop views at Kaiser Tiger. This place has good eats and craft beers, and will not disappoint.

  • Ballast Brewery

Located in Fulton Market, enjoy a day at this brewery with a nice cold glass of craft beer! Host an event or come here for a fun night out.

  • Cindy’s Rooftop

Last on our list is also one of the most Instagram-able spots in the city. VIEWS, VIEWS, VIEWS! Enjoy the views and a drink with your friends or loved ones at this hip rooftop bar located at the Chicago Athletic Association Hotel; also conveniently by the Gage!


This list won’t cover everything, but it’s a nice starting point. Whether it’s street, food, or music festivals, these will definitely enhance your summer!

  • Lincoln Park Wine Fest 2019

From May 17th-19th make sure to unwind with some wine after a harsh cold winter and enjoy the weather and some good company!

  • Aon Summer Fireworks at Navy Pier

From May 25th-Aug. 28th, catch the fireworks at Navy Pier (mostly every Wednesday and Saturday)! Be sure to get there at least an hour early if you want a good place to stand or sit, and get a good view.

  • Spring Awakening Music Festival

EDM is not for everyone, but if you enjoy this type of music and meeting new people, then be sure to check out your favorite DJs this year from June 7-9th.

  • Country Lakeshake

Country girl shake it for me! If you like Luke Bryan, Miranda Lambert, Keith Urban and more, then be sure to check out this little slice of country in our big city from June 21st-23rd.

  • Chicago Food Truck Festival

From June 22nd-23rd, 45+ gourmet food trucks will be gathered in the South Loop to satisfy all your foodie needs! Drinks and music will also accompany the food and tickets are only $10!

  • Chicago Pride Parade

This parade will be located in Boystown and whether you’re celebrating your pride or attending with some friends, this celebration will put a smile on your face on June 30th.

  • Tastemaker Tour Chicago

End your summer at Tastemaker from Aug.16th-18th at Revel Fulton Market where you’ll get to enjoy music, food, and drinks from local favorites to renowned chefs and restaurants. Make sure to buy your tickets early because they WILL sell out!


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