Your End of Summer Check List in Chicago

Welcome to Chicago!

As a born and bred Chicagoan I feel that it is my civic duty to tell you what are some of the best things to do in the best city in the world! Chicagoan’s deal with a brutal winter (sometimes -10 to -25 degrees) so we enjoy our amazing summers!

So sit back, relax and get ready for me to take you on journey through the Windy City on things you’ll absolutely love to do before the warm weather hits the road…

The Playpen/ Boat Rentals:

Nothing screams summertimes like going on a boat with your friends on Lake Michigan with the one of those ridiculous obnoxious pink flamingos rafts with a drink in your hand with getting ready to post the most insta-worthy photo of all time.

And if you’re like me and take LSD home (Lake Shore Drive, not the drug) and you see all those super cool people enjoying summer while on a boat, you’ll really know how to make people feel jealous.

The playpen is a blast but, do not fear, if you or someone you know doesn’t own a boat, which is a smart thing because you know what boat stands for, Bust Out Another Thousand, then head on over to where you can do daily boat rentals!

Ball games on the Southside or Northside:

Summer and baseball games go together like a good old-fashioned peanut butter and jelly sandwich! On the Northside of the city, Wrigley Field is filled with fun bars up and down Clark street and everywhere in between!

Also the Ricketts have put a lot of money into the area and they offer quite a lot to do besides drinking and watching a ball game.

If you’re interested in tickets you can get some here.

On the southside it’s a little different.

The ballpark is beautiful and has some of the best stadium food in the MLB. The Simba cam is also absolutely hysterical!

Yes ,they play the opening song from The Lion King and parents hold up their baby while the music is playing and Simba is on the jumbotron. 

But if you want to see the ballpark on a gorgeous night, go on a Friday or Saturday when the sky will be lit up with fireworks!

After the ballgame head on over to Shinnick’s Pub at 3758 S. Union Ave. to see one of the oldest bars in the city of Chicago. For ticket information click here.


When winters come and stay for a long time, Chicagoans get cooped up inside and we tend to get cabin fever.

So when the sun finally wants to stay out for longer than five hours there’s nothing we enjoy then an amazing rooftop bar where you can feel like you’re apart of the skyline and not just looking at it.

These are my top favorite places to enjoy that rooftop vibe

1) Aba 302 N. Green Street (3rd floor) 

Christina Slaton

2) Raised Bar Chicago 1 W Upper Wacker Dr.

3) LondonHouse Chicago 360 N Michigan Ave.

Concerts in the Park:

One of my favorite things the city does for FREE is concerts in the park at Millennium Park in the heart of downtown Chicago.

Nothing like bring your own assortment of cheeses, and meats.

While sippin’ on a bottle (or two) of wine while sitting on a blanket and taking in the beauty of this city. Here is a list of upcoming dates and details for the concert in the park.

The park only have a few more left so don’t miss out!

Boat Tour:

This city is filled with history everywhere you turn and the best way to learn about the history is on the Chicago Architectural Boat Tour.

With a variety of tours to offer including, Chicago River Boat Jazz and Cocktail hour,and Lake Michigan Navy Pier Firework Cruise.

It’s a great way to see the city and have a great time while doing it. For more information get everything here.

For my Chicago residents and dog lover check out the Shoreline Sightseeing tour lets you enjoy boat life while with your fur baby!

Lakefront Bike Rides:  

For the activity people out there who like to stay physical on their trips, the best way to do that in the city is to rent a Divvy and ride up and down the lakefront.

Ride from North Ave Beach to the Adler Planetarium to see another amazing view of the city. The views are so outstanding that it’s where I took my graduation pictures at.

Arlington Race Track:

Who enjoys betting on ponytails?!

Honestly, not me but I do enjoy dressing up in my Sunday’s best to watch the ponies while sippin’ on a cold beverage.

Arlington Race Track is just an hour outside of the city and never disappoints.

Brunch Spots:

What’s not to love about brunch? It’s a chance to wake up early get some breakfast while also get absolutely sh*tfaced at the same time where the judgement from others isn’t there.

AND you have more time to sleep it off and not be hungover the next morning. Win, win for everything!

Here are my top 5 places to Brunch in the Chicago:

1) Bub City 435 N Clark St.

This Bloody Mary bar is heaven on earth.

2) Stax Cafe 1401 W Taylor St.

3) Sweet Maple Cafe 1339 W Taylor St.

Warning they do NOT take reservations so expect a wait, but so worth it!

4) Summer House Santa Monica 1954 N Halsted St.

After brunch make sure you stop by the cookie bar!

5) Hashbrowns Cafe 731 W Maxwell St.

This is some good ole fashion brunch that doesn’t disappoint!

AVP Chicago Tour:

I grew up playing volleyball and still do from time to time and one of the things I love to do to finish my summer is going to the AVP Tournament at Oak Street Beach.

This event is free for generations admission, but if you’re interested in VIP tickets you can find them here. You can see the best of the AVP in Chicago on August 30rd – September 2nd.

You’ll get to see some of the best athletes that you know will be competing in the 2020 Olympics games. Think of it as a preview.

The energy is great, with a DJ that gets the crowd going and that backdrop is simply gorgeous! I mean, c’mon – look at this picture! Does it get any better than that?!

That’ll do it folks!

Go enjoy Chicago and have the best time ever while this heat still lingers!

— Jenna

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