Things to do in Chicago, where to go, when to visit. Chicago is my hometown! I have designed this itinerary based on a lifetime of knowledge.
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North America3 days / September 2022
Highs & Lows
The Lake is at it's peak temperature at the end of August/early September
The weather can be all over the place. One day its scorching hot, the next day it's freezing. Which can be hard to pack for.
This is my locals guide to Chicago. I have lived in many different places and also traveled all around the world and Chicago will always be one of my favorite cities on the planet. It is hands down my favorite city in the US. Chicago often gets overlooked by international travelers whose first US thought is NYC or LA. Chicago has a stunning skyline (unlike LA). Chicago has alleys which makes it a very clean city and the streets aren't full of trash (like NYC). AND it has strong midwest friendly vibes unlike both LA and NYC. All of this to say, Chicago absolutely needs to be on your bucket list.
Chicago can get extremely cold in the winter, along with a hefty amount of lake effect snow. BUT Chicago in the winter is still beautiful and hosts one of the best Christmas markets in the US. I am basing this itinerary off of my favorite month to visit, September. But Chicago has something incredible to offer every month of the year.
Q & A
How was the food?
I included a lot of my favorite spots in the individual locations BUT there are a few Chicago staples that you need to try. You can go to any location but a trip to Chicago is not complete without deep dish pizza (preferably Lou Malnati's over Giordano's), Portillo's for Chicago style hot dogs or Italian beef sandwiches, Nuts on Clark popcorn, and if you are looking for some drunk late night food, be sure to check out Weiner Circle.
What tips would you give a friend?
Chicago has a lot of jazz history which has left a great impact in the music scene. There is a great comedy club called Second City. Whatever you are interested in, you can most likely find it in Chicago. People are overall friendly so don't hesitate to ask for directions or help if you need any. Chicago has a lot of sports teams and though we aren't always "good" its always a good time! I highly recommend getting tickets to a Bears, Blackhawks, Cubs, White Sox, Bulls, or Fire game
Living in Chicago, depending on what time of the year you go, PLEASE wear layers and bring a proper coat. Chicago can be hot one day and freezing the next. Or in the winter it is just straight cold all the time. The cold, lake effect, and wind are NOT to be messed with. Chicago is nicknamed the Windy City because of political history but it indeed is very windy, especially around the base of skyscrapers. Wind chill is intense and its always better to be over prepared.
Chicago is very easy to get around. Both airports (ORD & MDW) have access to the L. The L is the "subway" system in Chicago. The L reaches all around the city and the most amount of lines can be found around The Loop. Chicago is very walkable, there are lots of scooters and bikes all around the city, and many Uber options as well. If you are only staying downtown, you do not need a car. If you are planning to venture out into the suburbs, I'd recommend booking something on SpotHero for overnight parking.
Chicago is a very unique and diverse city. They have a very strong Polish and Ukrainian population. I highly recommend exploring those neighborhoods or restaurants in that cuisine. Chicago also has an incredible Chinatown. Very authentic and has lots of incredible restaurants (and karaoke spots).