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Trip Report

A Local's Guide to Chicago

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.

by charfromchicagoAbout Me:Hey you! My name is Charlotte but most people know me as Charlotte from Chicago. I have been to 50 countries and all 50 US states. I have traveled on a strict budget, more luxuriously, and everything in between. I am a huge aviation geek... read more

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.

Itinerary Overview

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.

  • 3 Nights: Michigan Ave
    They don't call it the Magnificent Mile for nothing!
  • Day trip: River North
    Great neighborhood with lots of restaurants and bars
  • Day trip: South Loop
    The Loop & South Loop house most of the city's museums & the most iconic building.
  • Day trip: Chicago Botanic Garden
  • Day trip: Lincoln Park Zoo
  • Day trip: Bahá'í House of Worship
    Architecturally stunning and right on Lake Michigan

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

  • Packing tips?

    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.

  • Transportation Tips?

    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.

  • Any surprises?

    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).


  • Personally I think it is best to Chicago in multiple smaller trips rather than one huge trip. Chicago has 4 very distinct seasons which give the city a whole different feeling. I think one weekend at a time is perfect. So I'd recommend 2-4 nights at a time. Michigan ave is a great central place to stay. These are my top two recommendations for places to stay on Michigan ave: CitizenM and London House. CitizenM just launched their first location in Chicago. They are a unique hotel concept focused on affordable luxury. The rooms are small and compact but exactly what you need. Their new location is in prime location and within walking distance of the Bean. London House is a Hilton property and has arguably the best rooftop bar in all of the city. It is located right on the Chicago river across from Trump tower. You get incredible views of the city, river, and Lake. Bonus: it is right next to where you board the iconic architecture river boat tour which is my favorite activity in Chicago.