Chicago Summer Guide 2017

Tuesday, June 6, 2017

I love summers in Chicago, so naturally I love writing this post. The only problem is that I occasionally get overwhelmed with what to include/where to start so I'm just going to jump right in and let's see what happens.

I know one thing, this will definitely be a two-parter kind of post. Food and drink spots will come later (as that will be a harder/more in depth post for me to write because I think Chicago has the best food EVER.)

For now, let's start with my favorite daytime activities.

1. Street Festivals.
There's one every weekend and they're always a good time. Streets are closed down, tents are set up, bands play on every corner, and cold beer is served! It's as simple as googling "Chicago Street Festival + ( the weekend you're coming.)

2. Get on the water.
I suggest renting a pontoon or a battery operated boat and taking a cruise down the river. (Go for the pontoon, the battery ones will have you swerving all over.) Daytime is great to catch some rays, but I really like an evening cruise the best to see the city all lit up right while you're in the heart of it. Google is your friend, just search "Chicago boat rentals" and you'll find everything you need.

3. Rent a paddle board or kayak.
Either to play on in Lake Michigan, or to take down the river (the kayak, not the paddle board.) This is a great way to see the city from a new view.

4. Lounge at the beach.
Especially if you're staying downtown, it's super easy to walk to the beach and lay in the sand for a few hours. (Go early, it gets super busy!) Or stop into one of the beach bars and grab a margarita.

5. Root root root for the Cubbies! Or White Sox!
A baseball game is always fun. Back in the day when the Cubbies were awful we used to stumble into a game with $10 tickets. Unfortunately (or fortunately) that doesn't happen anymore.

Just want to be in the environment on game day? Go to Wrigleyville and drink at a rooftop bar nearby. The red line will drop you off across the street from the stadium.

6. Catch a movie in the park.
Parks all over the city host free movies throughout the entire summer. Pack a blanket, snacks, beverages, and enjoy a good old fashioned movie outdoors. Find the movie schedule here.

7. Go on an architecture boat tour.
Another chance to be on the water, see the city from a new angle, and learn some cool history on the buildings downtown. This is one of my fav things to do every summer!

If you're coming with kids... (don't. Jk jk.)

8. Lincoln Park Zoo.
It's about a 10-15 minute Uber ride from downtown and it's FREE! While you're in the area, take a walk around the gorgeous neighborhoods! We lived in Lincoln Park for over five years. In the summer, it's one of the most beautiful areas in Chicago, in my opinion!

9. Maggie Daley Park.
I've never been, but according to the photos I've seen, it looks very cool. (Google it!) Chicago is also known for its clean, safe parks located all over the city- many with splash parks in the summer!

Speaking of safe, several people ask me if Chicago is indeed "safe to visit." Yes, yes it is. Downtown, or in areas where tourists flock to in the summer, it's always heavily patrolled. I live about two miles from downtown and feel safer walking around here than I ever did living in Kansas. Any time of day, there's people (and dogs!) everywhere.

Also, public transportation is a way of life here and a great way to get around. That said, I don't typically take it alone, past 10 p.m. I have friends who regularly do, and say they've never felt threatened, it's just a personal choice of mine. Do what you're comfortable with in new surroundings. I suggest downloading a rideshare app like Lyft or Uber.

What did I miss? Probably a lot. That's just a quick list of some of my favs. Next up: best patios, rooftops, and food!


  1. There definitely is a real "safety in numbers" feel in big cities. Even if the city is known for more crime than smaller towns, walking alone down a sidewalk and not seeing other people can make you feel much more freaked out than wandering through a crowd.
    I've never been to Chicago and I'd love to go. I never would have considered renting a kayak or my own boat for the river but I think that would be so much fun!

  2. I've never been to Chicago but plan to go sometime in the future. It seems like such a fun place, especially the architecture boat tour. I LOVE architecture and exploring the city's design by water sounds so cool!

    Charmaine Ng | Architecture & Lifestyle Blog

  3. Agree on street fests! I actually saw you and Chris at Do Division last week! My husband and I were going with some friends to Fifty/50 and I gasped and grabbed him and said, "Mitch... that's Taylor, you know, The Daily Tay??" like I saw a celebrity. I saw Chris first and am pretty sure he's terrified from how hard I was staring in his face trying to figure out how I "knew" him... *insert see no evil monkey emoji*

  4. I have never been to Chicago and don't reckon it is a place I will ever visit

  5. Looking forward to the best rooftops post! I love a good rooftop. :)

  6. This makes me miss Chicago. I have always loved that city. I am now looking at airfare. Enjoy the summer in your beautiful city!

  7. Man, I love Chicago. However, I've never been there in the summer. I really think that I need to change that real soon.

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