You’ve got 48 hours (give or take) in the windy city. Unless you’re a Chicago native like moi, you’re probably asking yourself a series of questions about where to find the trendiest restaurants, fun places to sight-see, cute Instagram spots, and the best places to shop til you drop. There’s something special about Chicago, and if you get the chance, I highly recommend visiting at least once in your life! Here’s my ultimate guide to the windy city in a weekend!
Bites & Sips
Chicago has some of the best restaurants to choose from. Whether you want something sweet or salty, hot or cold, you’re sure to find a place in Chicago that will satisfy any craving.
Tons of Chicagoans rave about Stans Donuts. Not only do they have a super cute storefront, you can also catch the StansVan (aka a cute light pink van packed with delicious donuts for when you need a donut on the go!) If you’re looking for a trendy, youthful place to eat then definitely go to the Hampton Social. This place is the epitome of #instagramworthy. This is the perfect place to enjoy a nice glass of rosé or on a hot summer day, “frozé”. And don’t forget to snap a pic by their famous “Rosé all day” wall! Another must try restaurant is Shaw’s Crab House. My family and I love eating here because the food is incredible. You have to try the lobster roll. I promise you it’s an 11/10.
Sightseeing
Chicago is hands down one of the most unique cities that I’ve ever been too. The Chicago River running through the city and the proximity to Lake Michigan make it truly one of a kind.
Because of the famous Chicago River, river architecture tours are a popular thing to do for first timers. Visiting the Willis Tower is also usually on any Chicago tourist’s checklist. At the top of the building they have a cool glass skydeck with an amazing view that you can stand on and take pictures. (Just know that any true Chicagoan still refers to Willis Tower as the Sears Tower!) Oh and you definitely have to stop by Millennium Park and see some awesome sculptures too!
Activities
I love that there’s always tons of different things to do in Chicago. You can pack SO much into one day and can easily find activities that will cater to multiple different interests.
In the summer, Navy Pier is always fun to walk around! Navy Pier has a beautiful ferris wheel called the “Centennial Wheel” and there are fireworks every Wednesday and Saturday! Along with Navy Pier, Chicago has a huge variety of festivals such as the Blues festival, taste of Chicago, and Lollapoloza just to name a few. If you’re looking to do something that will really give you an authentic Chicago experience, try to squeeze in a Cubs game! No other baseball team compares to the Chicago Cubs and the beautiful Wrigley Field! And let’s not forget that the cubs were the World Series champs in 2016!!! Some other places that I enjoy visiting in Chicago are the Shedd aquarium, Science and Industry museum, and the Cadillac Theater. (My family and I just saw Aladdin at the Cadillac Theater and it was amazing!)
Shopping/Instagram Opportunities
If you didn’t go shopping and take an overwhelming amount of cute pics did you even visit Chicago???
The Magnificent Mile, also referred to as the “Mag Mile” is a huge stretch of stores and restaurants. I always make a point to stop by the gigantic Nordstrom! In terms of Insta opportunities, I highly recommend going to see the Bean, more formally titled, “Cloudgate”. The Bean is a huge mirrored sculpture shaped like (you guessed it) a bean, that has the most picturesque reflection of the Chicago skyline. Really anything previously mentioned in this article is perfect for an Instagram picture!
Chicago has it all: amazing restaurants, beautiful architecture, the best sports teams, and a fun vibe that you have to experience for yourself!
