There’s nowhere like Chicago, a city that offers everything in all the right doses. It’s a place that offers a virtually guaranteed great time, whoever you’re traveling with, even if it’s just yourself.
But it’s especially fun if you’re visiting with others, say friends, your extended family, or your work colleagues. We’d go as far as to say that it’s just as fun as taking a group trip to Las Vegas or anywhere else in the United States.
Why? Because there’s so much to do here, and since it’s a widely visited tourist destination (around 50 million people visit each year), everything you need to have a great time — hotels, restaurants — is already firmly in place.
Planning a group trip to Chicago? We’ve got you covered. Below, we’ve put together a few ideas that’ll ensure everyone in your traveling party returns home with plenty of happy memories.
Stay in a Top-End Hotel
We’d recommend staying in a top-end hotel regardless of your reason for visiting Chicago (because why not enjoy the finer things in life?), but we doubly recommend it if you’re traveling with a group and want to maximize your chances of having an awesome trip.
There’s no shortage of luxury hotels in Chicago to choose from, especially on the Magnificent Mile. Pool your money and book a suite where you can all stay together — it’ll ensure the fun never stops.
Where to Eat/Drink
Chicago is a foodie’s dream. It’s not an exaggeration to say that the city has a world-class food scene, and what’s even more fun is that you don’t necessarily need to go to a formal Michelin-starred restaurant to sample it (though feel free). There are plenty of places that offer delicious Chicago classics and modern twists while also providing a fun atmosphere, which is ideal for groups. Time Out Market always delivers the goods, while the Sterling Food Hall is also pretty special.
Fun Activities
The Windy City knows how to have fun, and you’ll find a virtually endless list of fun activities that are absolutely perfect for groups. How about a paddleboarding adventure on the Chicago River? Or catching a White Sox or Cubs game? Chicago also boasts one of the largest indoor entertainment centers in the country, where you and your traveling companions can race go-karts, go on rides, or do battle at the arcade. Whether you’re visiting for a weekend or a week, you’ll find that there’s never a dull moment.
Days in the Park
There’s much to see and do in Chicago, but one of the best things to do while visiting is…nothing at all. Well, not strictly nothing. Setting aside an afternoon to do nothing other than picnic in the park should very much be on your itinerary, especially if you’re visiting during Spring or Summer. Chicago boasts some of the best parks in the country, particularly Grant Park, Lincoln Park, and Millennium Park. Take a blanket, pick up some drinks, and enjoy all the great views this city offers.