Little Goat Diner

This four day itinerary provides a unique mix of Chicago's iconic landmarks, cultural experiences, diverse neighborhoods, and culinary delights! Adjustments can be made based on personal preferences and the time of year.

Read along with me as I tell you exactly how I spent the perfect 12 (ish) hour date night in Chicago with my husband and our two best friends. Reva, my fire wife and book bestie have recently entered our hockey romance era (didn't know that was actually a thing but here we are). After reading a couple hockey smut novels we found ourselves booking a trip to the windy city to enjoy a Chicago Blackhawks game...since it's valentines day next week we invited our hubbies to join us too ;) It ended up being the absolute perfect evening beyond fulfilling our hearts' hockey desires. We were led to the last standing prohibition era speakeasy, in the basement of the oldest building in Chicago. We shared a second hand smoke fueled nostalgic visit to one of the mob boss locales as well. Foodie finds on this trip were a solid 10 out of 10! Our hotel was just the right amount of classy yet affordable and we plan to return in the summer to spend time exploring the area on foot here too! If you enjoy this guide please do me a solid and save it to your faves and share with a friend and leave me a comment below :D Follow me on instagram for all my real time travel finds www.instagram.com/jesstakethetrip/ This is a living guide - if you save it you will receive future updates including any new places and deeper insights!

Welcome to the Windy City, located along the shores of beautiful Lake Michigan. Chicago is a hustling and bustling city full of over 70 unique & charming neighborhoods, amazing food and iconic landmarks. Chicago has so much to offer, there is something for everyone to enjoy. Fun fact: Chicago is NOT the capital of Illinois, even though it is the most well known city in Illinois (We see you Springfield). This guide includes everything from popular tourist destinations to local stops by neighborhood and tons of restaurants to try. While this is not an all inclusive list of what to do in Chicago, but its a pretty good way to start with over 150 options and tons of personal favorites! Get ready to plan your weekend of fun in Chicago depending on what neighborhood you're located in. Get ready to put on your walking shoes, as you are sure to get plenty of steps in walking around the city. Immerse yourself in the melting pot of cultures. If you're searching for a specific day-to-day itinerary for Chicago, set up a call and I will help craft the perfect trip based on your needs. Even if you only have a day (which only would begin to scratch the surface) it is absolutely worth it to make a trip to downtown Chicago.