Guide To Chicago

Wednesday, July 16, 2014

It's that time of year again... summertime in Chicago when I get several emails a week from people all over the country (and even beyond sometimes) asking for suggestions as to what they should do while visiting the Windy City.

To be quite honest, I love answering these emails because I love talking about Chicago. As I started compiling this list I realized there's far too much to say in one post so I might have to break this up into several segments. Unless of course I get lazy after writing this first post and decide not to write any others... Only time will tell.

disclaimer: I am in no way a Chicago expert and still often feel like a newbie in this city since I've only lived here about five years. However in those five years I've learned a thing or two about what I enjoy doing. Hopefully you do too!

Part 1: 10 Things To Do.

1. Go On An Architecture Boat Tour.
The history of the Chicago skyline is more interesting than you might think! See it by boat with a drink in hand and it gets even more interesting. I do this tour at least once every summer and I love it every time.

2. If an architecture boat tour doesn't sound fun to you, rent an electric boat instead and be your own captain as you cruise around the Chicago river. Pack some wine and cheese and this is always a good time.

3. Get out of downtown and head to the Lincoln Park Zoo (it's free!) And when you've had enough walk across the street to Mon Ami Gabi and have some oysters on their great patio.

4. Get your Ferris Bueller on at the Art Institute. I'm usually not cool enough to be an "art museum type of gal" but even I love the Art Institute.

5. Rent a kayak or paddle board. Kayaking down the Chicago river can be a little .... gross at times depending on how dirty the water is, but I usually enjoy it never the less. And paddle boarding in Lake Michigan is always a blast.

*Not my photo, but I bet these cute dads in plaid don't mind me posting them.

6. Go to a baseball game! Cubs or Sox, both are fun! And since our poor Cubbies are so bad you can sometimes find tickets for as low as $12! 

7. Catch an improv show! Go to any show at either Second City or iO and you will have a good time. Both theaters have produced more comedic stars than I can even count.

8. Speaking of comedy, let's talk about stand-up... Zanies is Chicago's oldest comedy club. It hosts some of the best comedians from all over the country every weekend. Of course the Laugh Factory is a great venue as well.

9. And let's talk even more stand-up. Besides the more well known clubs like I mentioned above, there's also a ton of other awesome comedy showcases going on every night featuring some of my favorite comedians in the city. Such as...
Comedians You Should Know- every Wednesday at 9 p.m. in The Back Bar at Timothy O'Tooles.
Parlour Car- every Thursday at 9 p.m. at Bar Deville.
Hoo HA Comedy- every Tuesday at 8 p.m. at ROCKIT Burger Bar.
This Week's Show- every Thursday at 9 p.m. at Bar Celona.
Going to one of these shows is a great way to get out of the tourist bubble and check out some local spots!

10. Last but not least, you should probably go to Millennium Park and take a photo by the "the bean" just because you have to or no one will believe you actually came to Chicago.

There you have it; a few things to do when you come to Chicago this summer. And most importantly, don't be afraid to take public transportation! The friendships you form with the homeless people you sit next to will last a lifetime! Just kidding, the CTA isn't that bad. Usually.

Part 2 will be about where to eat... In the meantime, click here to see my favorite Bloody Mary's in the city.

Chicago friends, have something to add? Let me know below!

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  1. My boyfriend lives in Chicago and every time I come down there we go to the Lincoln Park Zoo just because! And when I come down in a few weeks we are going to a Cubs game. I am so excited!! :) I love experiencing more and more of Chicago each time I'm there.

  2. lol take a photo of the bean or else no one would believe you are there. that is funny

  3. Wow you've done a lot of fun stuff! Chicago seems pretty awesome and beautuful.

  4. I live here and people who visit usually always want to see the Sears Tower so I would add that as a must. or an alternative drinks at the Hancock signature lounge (its amazing, the view and the booze)

  5. this guide is awesome!!! it's always my favorite to get emails asking me about what to do (usually for tomorrowland but still) makes me feel like my blog is worth it!

  6. I say this every single time you write about Chicago, but I want to visit so badly. Great guide, I will definitely be saving this for that hopefully not too far off trip.

  7. Rent a Divvy bike and go from festival to festival. There are Street Fests going on all over Chicago all summer! You'll eat like it was your last meal. You'll bike for miles and still gain weight!

  8. I was there two weeks ago and did the boat tour! Totally worth it!!!

  9. Wow, seems like a fun place. Ill add it to my list of places I wanna visit, and hopefully make it happen one day.

  10. I'll be in Chicago on August 24-27, staying near Feeding America. Are there any awesome things going on during that time (possibly in that area) that you would call don't-miss?

  11. I've been trying to plan my Chicago trip to visit my best friend's family for two years now, and it still hasn't come to fruition yet. Which sucks b/c we talk all the time about going to Second City and Navy Pier and the Chicago Eataly and all...

  12. We were just there last weekend...I couldn't begin to narrow down the restaurants I wanted to go to.

  13. I'm not going to lie... I intentionally avoid The Bean whenever we're in Chicago. I like to pretend that I'm too cool to conform. Really, I just don't want to deal with the crowd that is inevitably always there.

  14. Oy, I've been here 5 years and I've yet to go on an architecture tour. I'm trying to be more appreciative of the fact I live in this awesome city by attending more events. Too bad the first one I planned on got cancelled last Saturday! From the looks of Instagram pics of the Taste of Chicago treats, I missed out!

  15. I like the idea of the Mafia Tour - I have yet to do it since moving here, but you can take a tour of all the places the major mobster stuff happened in Chicago. :)

  16. Love this list, bookmarking it. Finally making my way to Chicago for the 1st time ever in September... architectural boat tour, the bean, and a Cubs game are definitely on the agenda. I also want to check out Three Dots and a Dash... is it worth it?

  17. Never been there but it does sound like a nice place to visit

  18. The Bean & Electric Boats are both on my list of must do's
    Chicago is one place I'm determined to visit

  19. We're casually pursuing a house that popped up on the market, but if that doesn't happen we're scheduled to be in Chicago over Labor Day weekend. Great guide! Thanks!

  20. I booked our tickets this morning to go to Chicago in a few weeks and of course this post was the one I made sure to visit first! ;) You can't think about Chicago without thinking about you. So, thanks for making me all kinds of excited already!

  21. Hey! I am planning a trip to Chicago at the end of November with my boyfriend and I was wondering if you have a guide like this for the winter? It's our first time to this city so we want to make sure we don't miss any top spots! Any restaurants or hotels/areas that you would recommend? Thanks!

    I am definitely going to be trying some of the places you've mentioned before for a good bloody!