Chicago is my city. It is the first place where I discovered the eccentric offerings of places and spaces. From the El to the all the different neighborhoods that you can just happen to stumble into from a decent walk, Chicago has it all. I grew up about an hour north of the city, yet taking the Yellow line into the Red line into downtown was something I looked forward to whenever my family was planning to go. Now I am living in the heart of it all. I can spend the day exploring new cafes, book stores, and architectural sights all at my own leisure. I could take an entire book to talk about how much I love Chicago, yet here I will give my essentials.
Whether you are coming in from O’Hare, train, or car, you will probably want to end up downtown at some point during your visit, major key: do NOT park downtown. Find a parking lot in a neighborhood, or if you are coming in from a suburb or Metra train, park at a train station for a day. The charge is usually no more than five dollars, where if you are parking downtown expect to spend well over $30 for a day sometimes more if you do not know where to look. Best scenario, you have a friend or relative near the city and you can use their space for the day. After you figure out your transportation, my itinerary requires a train ride. Ventra is the Chicago card system you pay for the train, buy a day train pass so you do not have to reload it throughout the day. Trains come every few minutes for any color line so no need to worry about making a specific train. If you are coming in the winter time make sure to bundle up. We may be called the Windy City for our politicians, yet it is also quite chilly and if there is wind coming off Lake Michigan, get ready to “have icicles hanging from your ears” as my California relatives mock when they visit.
I live on the North side in Lincoln Park, so my suggestions may be a bit biased, however, most would agree with my go-to places. Brunch is not only a time to eat, it is also a verb in my vocabulary, so it is time for brunching. Grab some friends or family and head on over to my stomping ground in Lincoln Park, accessible from the Fullerton Red line or the Armitage Brown line. Summer House Santa Monica is a vibrant place for brunching, as well as lunch and dinner that are also fine options for this venue. It has unique dishes as well as a clean and fresh ambiance and amazing menu options from Salmon Hash to Belgium waffles along with amazing fresh coffee you simply cannot go wrong. The desserts are a main staple of this stop, there are amazing cookies as well as tarts and other sweet delights, which are all for display when you walk in the door. Along with the amazing food options, the photo ops for Instagram are just as necessary. Another option is Toast, this was one of the first breakfast/brunch places I went to when I moved to the city and I go back all the time. They have a scandalous dish rightly named, “The French Toast Orgy.” It is stuffed French Toast with mascarpone, strawberry, and dark chocolate filling. I substitute the dark chocolate one with another mascarpone piece since the chocolate is a bit intense, however if you have a major sweet tooth by all means dig in. There is also amazing coffee and if you want to turn it into a bit of a boost brunch, the Bloody Mary’s are perfect.
After you are done brunching, make your way East towards the lake and take a stroll through Lincoln Park. There is Lincoln Park Zoo, the boardwalk, and beautiful views of the lake all to enjoy for free. A frequently missed location by visitors is the Alfred Caldwell Lily Pond. It is right behind Lincoln Park Zoo and it is a quite secluded place with beautiful views of the carefully planed ponds within a tree covered canopy. It is a perfect way to work off brunch. If you are visiting in the warmer months, there is also the Green City Market. A bunch on vendors from around Chicago and the Midwest come to sell fresh fruits, vegetables, spreads, crepes, jewelry, and crafts. It is a great time to explore and it is on the way into Gold Coast.
Gold Coast is for the luxury shopper in us all. Hermès, Chanel, Dior, Saint Laurent, and much more. It is the perfect place to do some window shopping or some splurging. There are also some of my favorites such as Madewell, Marc Jacobs, and Rag and Bone. Go in take in the pristine views of high fashion. Walk down Oak Street and then down Walton, you will find the signature Sprinkles Cupcakes. My personal favorite, Red Velvet is always available in store as well as in the innovative Cupcake ATM. Simply make your selection of your favorite flavor, and then out comes the cupcake all boxed up and ready to enjoy.
Make your way down the street to Michigan Avenue. If you want to avoid the crowds go early in the day on a weekday, if thats not an option then prepare yourself for crowds of tourists. If walking down Michigan Avenue is a must, go for it, if not then avoid the hustle of frustrated city dwellers and the dazed confused tourists. Take a few back streets around the crowded sidewalks and only pop out on the main avenue when necessary such as when visiting Tiffany’s or taking pictures of the beautiful John Hancock lobby. You will make your way past the Chicago Tribune building with its Gothic revival architecture, then across the Chicago River back on Michigan Avenue. You just left River North and entered the Loop when you cross the bridge. Stroll down Michigan a bit further and you will see the iconic Millennium Park, yet right across from the ice rink/ Park Cafe, is the frequently overlooked Cultural Center. Another amazing Chicago architectural sight, there is a Tiffany glass dome inside as well as gorgeous interior details. There are unique exhibitions year round and it is also free to take a look inside. Right next store, on the Washington Street side there is a French cafe, Toni’s. One of the best cups of coffee I have has as well as small dishes and full on meals. Take a break from walking and enjoy the simplistic scene. Take your Instagram worthy stroll through Millennium Park then, if you are an art enthusiast or you would like to get started, head on over to the Art Institute. Tickets are not too pricy and you get to see a bunch of original pieces of artwork. Go see Monet and Van Gough, yet do not forget about the unique exhibits that are there on occasion. I am lover of the little rooms on the lower level, it teleports you into different little worlds frame by frame, a definite must. When leaving, make sure to stop by the gardens on either side of the museum. They are beautiful and great places to sit and reflect.
Right across the street on the corner of Jackson and Michigan is the Chicago Architecture Foundation. Walk in the front door and there is a 3D map of the city in the lobby. Go up on the stage and you will discover it is interactive with a bunch of statistics about different parts of the it as well as urban planning facts. Another place that is overlooked, yet necessary to understand the full effect of Chicago.
To take a bit of an adventure, hop on the blue linear Jackson Boulevard going towards O’Hare and make your way to the Damon stop. You are now in Wicker Park. My new found favorite of my early twenties. Everything here is colorful and eccentric. From food such as Big Star Tacos, The Furious Spoon Ramen, Stan’s Donuts, and so much more, there is a store front for everyone. From record shops to book shops, so many places are ready to explore. Dedicate your evening to taking pictures by murals and going on a hunt to find a secret speakeasy, a password is required and I will leave that fun to you. Ask around, get to know some people and they may be in the know of where to go.
Chicago, my love, you are wonderful. There are consistently new places to explore and the sights never get old. Of all the places I go, I know I will always call Chicago home. Let me know if you have more suggestions. I will have plenty of more posts about my adventures here. I keep a running spreadsheet of places I go, and I am always looking for more to explore!