OUR ULTIMATE COVID BOOKING GUARANTEE. FIND OUT MORE
As the third most populous city in the United States, Chicago is filled with people who are looking to have a good time. The Windy City offers something for everyone, from outstanding live shows and renowned museums to greasy, delicious pizza. These are the top things to do in Chicago.
Chicago’s 18-mile (29km) lakefront path spans the entire east side of the city. It’s a picturesque place to spend a sunny day walking, biking or running beside beautiful Lake Michigan while also seeing gorgeous views of the Chicago skyline. Along the way, you’ll pass dozens of free parks and public beaches where you can take a rest, play some catch or go for a swim. The path recently underwent a massive expansion. Now, bikers and pedestrians use separate lanes, making it safer and more enjoyable for everyone.
No matter what season you find yourself in Chicago, there is bound to be a professional sports game to see. Chicagoans love their Blackhawks, Bulls, Bears, Cubs and White Sox, and even the frigid winter temperatures won’t stop them from getting out and supporting their teams. If you dare, bundle up for a mid-winter Bears game at Soldier Field, or wait for the sun to come out to enjoy a baseball game at Wrigley Field or Guaranteed Rate Stadium. You can also leave the weather out of the equation and watch the Bulls or Blackhawks play indoors at the United Center.
Hop aboard this boat cruise and spend time winding down the Chicago River while learning stories behind the fascinating architecture you see along the way. Chicago’s architecture is truly one-of-a-kind, and this fascinating tour is beloved by locals and tourists alike. If you’re interested in taking a cruise but architecture isn’t your thing, try a cocktail cruise or a sunset cruise, or one with live music. This city is interesting whether you see it late at night or early in the morning.
No visit to Chicago would be complete without at least one slice of deep-dish pizza, though the best place to get it is up for debate. Lou Malnati’s, Giordano’s, Pizzeria Uno, and Pequod’s are all city favorites. No one knows officially who invented it – but it’s distinctively delicious and consists of a high-sided dough filled with cheese, tomato and toppings. If you’ve got time and room in your stomach, why not try all the varieties and decide the best one for yourself?
Every August, millions of people gather for a weekend on Chicago’s lakefront to watch a fleet of military jets flip and spin through the air. The show, which is completely free, can be seen for miles along the shoreline, but is best viewed from a boat, rooftop or beach. Pack a picnic to take with you, or take the opportunity to try a Chicago hot dog, made with beef and a large selection of distinctive toppings.
Along the most central part of the Chicago River, running right through downtown, is a pedestrian walkway stretching just over a mile (1.6km). It’s a lovely place for a stroll and offers a taste of nature in the city. There are any number of attractive waterside restaurants and bars to drop into while you’re there, or you could try renting a kayak to see the river from a different perspective. There are also lots of areas to simply sit back, relax and watch the boats drift by.
Chicago has so many amazing museums to choose from, and, with CityPass, you don’t have to pick just one. Instead, you can spend $108 (£83) per person, or $89 (£68) for children, to have access to five of them. Easy to use and great value, it’s not something to miss. With one CityPass, you can visit the Shedd Aquarium, the Willis Tower Skydeck, the Field Museum of Natural History, the Adler Planetarium or the Art Institute and the Museum of Science and Industry or the John Hancock Center Observation Deck.
Chicago is so much more than its downtown area. Its many neighborhoods are full of culture and wonderful things to do. Spend an afternoon enjoying Pilsen’s National Museum of Mexican Art, shopping local in quiet, pleasant Andersonville or wandering Edgewater’s Bryn Mawr Historic District. You can also head to the Old Town for more things to do, including famous beer pubs, shops selling artisanal fudge and spices and a wonderful old-time feel as you stroll around the neighborhood taking everything in.
There is live music available all over this city. During your visit, find out what’s playing at some of the city’s best local venues, such as the Vic Theatre and the Aragon Ballroom. For dinner and a show, try Andy’s Jazz Club or Schuba’s Tavern. In the summertime, Millennium Park offers a free, outdoor weekly concert series. And if you’re willing to spend some money, a concert at Wrigley Field is an unforgettable experience – names including Paul McCartney, Jimmy Buffett and Elton John have played there.
Chicago really knows how to entertain its visitors. The Logan Theatre has been churning out fantastic evenings since it opened in 1929, and it’s still going strong. But don’t expect to see the latest Hollywood blockbuster every visit; you can see something a little different here. From renowned arthouse classics to the latest documentaries, you definitely won’t be falling asleep in the back row. Even the design and interiors are eye-catching – this is how cinemas were meant to be. The cherry on the cake is that it tops its popcorn with real butter.
Additional reporting by Alice Johnston.