Curator’s statement
Chicago is a foodie’s paradise. From steakhouses to pizza to seafood right on the water, this is the best place to experience new culinary tastes. The Windy City will give you the best experience outside of food as well. If you’re a Harry Potter fan, one of the biggest stores I’ve seen is here and is a great place to enhance your collection, and the River Walk will easily be the highlight of any trip.
The Fora Difference
Book with Tiajuana Gilmore to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay in Chicago
Unlock perks by contacting Tiajuana Gilmore to book your trip.
Things to do in Chicago
Wide shot of the Chicago Riverwalk
Explore the Riverwalk: It’s about a one-mile-long walkway filled with different shops, restaurants, and cafes right along the Chicago River.
Andy’s Jazz Club: One of the best jazz clubs in Chicago. It has a $20 cover, but it’s worth it between the food, drinks, and live music—it’s a must-see.
See The Bean: Iconic sculpture that’s located in Millennium Park. It’s shaped like a bean, hence the name. It’s also great for pictures and grabbing a quick bite to eat, as there are a few cafes surrounding it.
Visit the Medieval Torture Museum: Not for the faint of heart, kids, or squeamish, but if you’re a morbid history buff, please visit. The whole museum takes about 45 minutes to an hour to go through and has interactive displays to truly understand each method.
360 Chicago Observation Deck: It’s the best way to see Chicago’s skyline. It’s 94 floors up and you can look out from the top on tilting glass.
Places to eat & drink in Chicago
Wildberry Pancakes and Cafe: Great place to grab one of the best vegan hashes or huge pancakes. The coffee isn’t bad either and the seasonal options are endless.
Labriola: If you want authentic Chicago pizza, stop here. The pizzas are amazing and flavorful with endless toppings. They also have both alcoholic and non-alcoholic drink options.
The L Station: One of the best places to get soul food near the Chicago Loop. If you love spicy food and good drinks, stop here. The staff and service are amazing and will make sure you enjoy your meal and feel like a family member.
Il Porcellino: The legend of II Porcellino says you must eat here for good Italian. Grab the fusilli pesto Genovese if you want a vegetarian option with full flavor, and pair it with rose wine.
The Dearborn: Great drinks and a perfect location close to the Chicago Theater. The decor inside is so inviting, you’ll want to stay to try the whole menu, including the Midwest fried chicken.
Chicago Chop House: A traditional steakhouse with fine dining service. If you can, grab a seat in the courtyard—it has the best view for enjoying your ribeye.
Need to know
This city is mostly walkable with beautiful sites. Grabbing a taxi, Uber, or Lyft is very easy, or you can take a water taxi all over the city. Take in a show at the Chicago Theater—it’ll be the best experience. Take a bus tour as well and dress warmly—the wind is high!
Travel Advisor
Tiajuana Gilmore
Tiajuana Gilmore
Get in touch with Tiajuana Gilmore
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
For more inspiration and insider recommendations, visit our Chicago page.