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.
North AmericaUnited States3 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.
Hands down the best activity to do in Chicago is a river boat architecture tour. There are multiple tour companies that offer this and it is a MUST. I recommend it for locals too because it gives you a completely different perspective of the city. Chicago is architecturally stunning and has so much history. Please note that this is a seasonal activity. The tours run spring - fall, weather permitting.
Millennium Park is Chicago's version of Central Park. It is located in a central part of the city and has lots of greenery. It's home to The Bean, Buckingham Fountain, and much more.
Bonus: the world's first Nutella cafe is right off Michigan Ave. Highly recommend going and grabbing some crepes or Nutella coffee and treats.
River North is a great place to explore when you are looking for food or drinks. It's a pretty young neighborhood and has a lot to offer. Siena Tavern is a great Italian restaurant which an amazing octopus appetizer.
If you are looking for something sweet, JoJo's Shake Bar has incredibly over the top milkshakes. Ghirardelli also has something for anyone's sweet tooth and the building is beautiful!
Take a walk over to the world's largest Starbucks! Though I typically encourage local spots over mega chains, it is still a fun experience to visit this multi floor coffee giant. They have special things on the menu that you can only get there or at other Reserve locations. My favorite is ordering an affogato.
Headquarters Beercade is one of my go to places to drink and hang out. It is a bar full of arcade games. It is free to play the games which is a huge bonus.
When you think of the Chicago skyline, the Willis Tower (forever known to locals as the Sears tower) is what typically comes to mind. It is the third tallest building in the US and home to The Ledge, 4 glass boxes that hang over the side of the building at its observatory floor.
The Loop and South Loop hold almost all of Chicago's famous museums. If you have the time and plan on visiting multiple museums during one trip, the most cost effective option is to buy a City Pass. You can buy a pass that allows you to visit multiple museums, skip lines, and bundling will save some money too.
You can channel your inner Ferris Bueller at the Art Institute, visit a world renowned aquarium at the Shedd, or stop by to say hello to Sue the dinosaur at the field museum.
The Lincoln Park Zoo is in the north part of the city. Chicago has two zoos and this one happens to be free and easier to get to. It is right off of Lake Shore Drive and gives you great views of the Lake as well. It is also the fourth oldest zoo in the country. It is not as large as the Brookfield Zoo but still a good time. Then after you can explore more of the Lincoln Park area or head over to Wrigleyville.
The Baha'i temple is a non-denominational house of worship. It is such a beautiful building and it is open to everyone. It is outside of the city and you'd need a car to get there but it's such an huge piece of history to the North Shore. It is right on Lake Michigan which brings amazing views. Sheridan Road is famous for having large and expensive houses so the drive there is even more interesting. From downtown you'll head north on Lake Shore Drive and you are running parallel to the Lake almost the whole time.
Q & A
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.
Tips you would 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).