Summer in Chicago with @JenTravelsLife #ThingsToDo #Travel

You ever get people asking you the same question over and over again?

Like “Where did you get those shoes?” or “What’s the best place to go for pizza?” or “Why aren’t you married yet?”

Anyway- this is my list of top summer picks in Chicago.

gogobot hands #travel

Lakefront Path

Walking along the lake is one of my favorite places to take a visitor, regardless of the time of year. Great place to ride a bike, walk a dog, go for a jog or hold hands with your sweetie. There are endless photo opportunities with the peaceful and calming water that feels so far from (and yet so close to) downtown.

Millennium Park


Millennium Park is absolutely what make Chicago great. The vision that they had in creating so much public land near Lake Michigan was brilliant. Even if you’d outlive in the city all the CTA converges at millennium Park so you can get in and out with no fuss. It is an absolute must-do regardless of the time of year.

The Signature Room at the 95th


Sure it’s in the top of every Chicago tourist’s list but there’s good reason. The view from the 95th floor of the Hancock Building is truly exceptional any time of day. If you time it correctly, you can even watch Navy Pier’s weekly fireworks show while you wine and dine. Locals know some of the best photo opps are in the women’s washroom. An absolute “must do” in Chicago!

Ravinia Festival


Clarence Buckingham Fountain


When you are in the Millenium Park area, Buckingham Fountain is a “Must Do”, especially in summer. It’s a gorgeous backdrop for pictures and was in the opening scene of “Married with Children”, the 80′s sitcom.

Wrigley Field  Wrigley Field travel


I was not a fan of the Cubs or beer until I went to Wrigley Field. I hope this place never changes. I know that there are efforts to upgrade but it is so cool just the way it is. I will say yes to a game at Wrigley Field even if I don’t know who’s playing. For some reason a hotdog tastes better when six people had to pass it to you.



Great spot for low-key lounging with friends or on a date. Located in the heart of River North, if you can snag a patio table, you’ll be in people-watching heaven. Can’t go wring with a pizza and house wine.

Mario’s Italian Lemonade

Grant Park



Oak Street Beach

Wendella Sightseeing Boats


Chicago Segway Tour


Macy’s State Street


Lincoln Park Zoo


I love that the Lincoln Park Zoo is always free and open year-round. And they are trying to do good by the animals in the zoo yet somehow I found the experience kind of sad.

Chicago Cultural Center


Jay Pritzker Pavilion

Garrett Popcorn


Garrett Popcorn brand needs no introduction. Yes, it IS as good as they say and they lines can be a bear at certain locations and certain times. There really is no one that does a better Chicago Mix of Cheddar and Caramel flavors.

Tavern On Rush – Steakhouse


When I decide to show someone the “Viagra Triangle” this is usually the spot that we spend the most time. There’s always an excited and eclectic crowd drinking martinis and feasting on fresh seafood appetizers and steak dinners.

Piccolo Sogno


I dated a guy that took me here a few times and that might be part of the reason I kept dating him. The food and service are top notch and though it’s not cheap, it’s not quite as high as some of Chicago’s other stellar restaurants. Everything on the menu is amazeballs.

If you can score a table on the deck- you won’t be disappointed. The trees, the laughter, the wine… Just make sure you don’t mistake your love for the venue as love for your date. :)

PERFECT date night venue.

Devon Avenue

If you love Indian food, this is THE area to be! It’s like a whole other world of culture in this neighborhood. Make a day trip of getting a henna tattoo, shopping and, of course, eating.



Founded in 1983, Chinatown is a fantastic example of a culturally progressive neighborhood. Though people from all over the world visit- the locals manage to keep the energy, and vitality of the Asian culture alive with no apologies. A walk through Chinatown can be an educational history lesson on the customs of the Chinese American community.

Michigan Avenue Bridge

I love all the bridges in Chicago because they merge beauty, photo opps and function all in one. If you see people trying to take a picture and you’re not in a hurry- offer to take it. It’s what a local would do.

Shoreline Water Taxi


Vertigo Sky Lounge


Beautiful venue and beautiful people. Atop the Dana Hotel, Vertigo boasts spectacular views and pricier-than-average cocktails. If the weather is nice- the outside deck is is a little slice of magic.

ROOF on theWit


Another great spot to appreciate views of Chicago. Be prepared for a long line on the weekends while “VIP”s sweep past. The cocktails are beautiful, as is the crowd, but I’d bring my own company anyway.




Jen Knoedl is Executive Producer of JenChicago Productions, as well as its enthusiastic video host. Click here to find out about sponsorship and partnering opportunities regarding travel, Chicago and entrepreneurship. Tweet Jen at @JenTravelsLife

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