From eats to must-see sights, here’s all the best places to go in Chicago.
“Chicago is one town that won’t let you down. It’s my kind of town!” Frank Sinatra was right when he sang about Chicago in “My Kind of Town.” As the third-largest city in the U.S. behind New York City and Los Angeles, Chicago is vibrant, exciting, and lively. When my fiancé, Ferdy, was called to work there on a job, I had the pleasure of going to the Windy City with him and my goodness, the city was incredible!
To inspire you for your own future travels, I have rounded up all of my favorite eats and sights from my trip to Chicago, so if you get the chance to head out to the amazing Windy City, you’ll be prepared!
Where to Eat
Important things first: FOOD! From delectable treats to Chicago classics, these were my faves.
You can’t go to Chicago without having a deep-dish pizza. I’m telling you, once you have a slice of this classic Chicago dish, you won’t go back to regular pizza ever again. We ordered the Deep Dish Malnati Chicago Classic™ deep-dish pizza, which had salty sausage, creamy mozzarella cheese, and tart, vine-ripened tomato sauce on a buttery crust. It really doesn’t get any more authentic Chicago than this. After eating our scrumptious pie, I quite literally fell into a food coma. If you can’t make it out to there just yet but want to bring those classic Chicago flavors home to you, Lou Malnati’s ships nationwide! (I might just have to order some to last me until I can go back!)
The Famous Dutch Pancake Huis (Pannenkoeken Cafe)
Ferdy as you may know is Dutch and pannenkoeken is a classic dish in his culture, so we were excited to try the Dutch pancakes at the Famous Dutch Pancake Huis. Ferdy got the traditional apple pannenkoeken and I tried the chocolate banana one. They were both so insanely delicious! Besides the sweet pannenkoeken, they also offer some savory ones like bacon and cheese or sausage, mushrooms, and cheese. If you’re looking for a yummy way to start your day that’s a little different than your standard breakfast, I highly recommend the Famous Dutch Pancake Huis.
After seeing this marshmallow café in a Buzzfeed “Bring Me” video, I knew I HAD to go to XO Marshmallow. Besides being every marshmallow lover and color enthusiast’s dream (have you seen their café?!), XO Marshmallow offers up some seriously delicious treats. From frozen and hot drinks to s’mores, Swoon Pies (which are similar to Moon Pies), Dream Bars (which are like Rice Krispy treats), and an array of exciting marshmallow flavors, they have all the goods. Make sure to stop by for some marshmallow-y goodness! You can also check out XO Marshmallow online and they ship their treats nationwide!
The Original Rainbow Cone
For the perfect, totally Instagrammable treat, make sure to visit The Original Rainbow Cone! Their rainbow ice cream cone is truly the prettiest ice cream you will ever see. It’s also great for those that always have a hard time deciding which flavor to get because you get them all. The Original Rainbow Cone, the shop’s signature cone, comes with not one but five flavors: Chocolate, Strawberry, Palmer House, Pistachio, and Orange Sherbet. All together, they make a perfect rainbow that is absolutely delicious.
Stan’s Donuts and Coffee
One morning in Chicago, Ferdy and I wanted something quick yet sweet and delicious for breakfast. We stumbled upon Stan’s Donuts and Coffee when looking for places to go and took a little walk on over to the shop. The retro vibe of the shop instantly sold me when we walked in, but the donuts were amazing! They offered every type of mouth-watering donut you could think of from the classic Maple Long John, Chocolate Glazed, and Apple Fritter to the exciting and bold Lemon Pistachio Old Fashioned. There’s a little bit of donut magic for everyone at Stan’s.
Sights to See
There is so much to see when you go to Chicago, and this list in no way covers them all! These spots, however, were some of my highlights, and I think you’ll enjoy them, too!
The Start of Route 66
Ferdy and I had been to the start/end of Route 66 in Santa Monica, so seeing the East Coast start/end of Route 66 was a must for us. Once one of the most popular interstates in the U.S., you can find several Route 66 signs in Downtown Chicago, but the best one is the sign that marks the start of the historic route. Now, we just can’t wait to drive down it in its entirety!
The DuSable Bridge offers spectacular views of Chicago. By simply standing on the bridge, you will get to see some of the Windy City’s architecturally significant buildings, including The Wrigley Building and Tribune Tower, and a breathtaking view of the river.
Speaking of the Wrigley Building—it is perhaps the prettiest skyscraper in Chicago, making the building a must-see. With its iconic clock tower, you’ll definitely get the perfect travel picture. (I know I did!)
After visiting the Wrigley Building, head on down Michigan Avenue for the ultimate Chicago shopping experience. From Coach and Tory Burch to the Gap, they don’t call it the Magnificent Mile for nothing! The premier shopping district offers an array of shops for everyone, along with plenty of dining options. However, my favorite part of the Magnificent Mile would have to be the Starbucks Reserve Chicago Roastery. I absolutely love Starbucks and this location happens to be the largest Starbucks in the world! You could easily spend the entire day on the Magnificent Mile shopping and enjoying your Starbucks coffee!
If you’re lucky enough to go to Chicago during the spring, like Ferdy and I did, you’ll be able to witness the beauty of Chicago’s tulips. The tulip beds line Michigan Avenue, stretching from Roosevelt Road at the south end of Grant Park to the north end of the Magnificent Mile at Oak Street. The Chicago Department of Transportation organizes the planting of the tulips and each fall, over 100,000 bulbs from my favorite place in the whole world—the Netherlands!—to be planted. In mid-to-late April thousands upon thousands of bright and bold tulips line the streets, and several of the shops along the Magnificent Mile coordinate their window displays to match the tulips outside. The tulips are definitely a sight to behold while in Chicago.
Navy Pier is one of Chicago’s top attractions and offers an eclectic range of activities, rides, games, shopping, and dining. But perhaps the most famous attraction of Navy Pier is its Centennial Wheel and is a necessary stop during your trip to Navy Pier. Standing nearly 200 feet high, the Centennial Wheel offers unbeatable views of the city and Lake Michigan. Plus, you can even catch Lake Michigan and Chicago River cruises from Navy Pier!
Lakefront and Riverwalk
Chicago is definitely surrounded by beautiful bodies of water and it was so fun to explore all of it. I highly recommend walking along the lakefront and enjoying Lake Michigan or cruising down the Riverwalk in Downtown Chicago. Along the Riverwalk, you can also take a boat ride or go kayaking, enjoy several eateries, and watch the Centennial Fountain & Water Arc, which sprays over the river!
Cloud Gate, or “The Bean” as locals call it, is a public sculpture in Millennium Park. One of Chicago’s most popular sites, Cloud Gate reflects the city’s famous skyline and the surrounding green space. The sculpture’s polished surface invites visitors to touch the surface and observe their own reflection, making it interactive and fun. So, make sure to put “The Bean” on your itinerary!
The Chicago Theatre
If you enjoy theater like I do, then make sure to add The Chicago Theatre to your list! A legendary theater in the heart of Chicago, it’s a great place to catch a show while in the city. Plus, the inside of the theater is absolutely spectacular and alone makes the trip well worth it. Make sure to check their website for the latest plays and shows running at the theater!
If you are a sports fan, I highly recommend making a stop at Wrigley Field, home of the Chicago Cubs. Check their season schedule to catch a game, or just stop by the stadium to catch a picture with the iconic Wrigley Field sign!
Last, but certainly not least, is the Willis Tower! I was lucky enough to see the building every day from our hotel and it is magnificent, especially when they light the spires up at night. If you’re not too scared of heights, you need to visit Skydeck Chicago at the Willis Tower. At 1,353 feet in the air, the Skydeck offers spectacular views, spanning up to four states! And you get to see it all from glass boxes that extend out 4.3 feet from the building! (Did I mention that the Willis Tower is the third-tallest building in the nation?)
I hope you add some of these destinations to your itinerary when you visit Chicago! Enjoy the Windy City!