Chicago is world famous for its comedy. The seemingly endless list of legends who got their start performing at the city’s many theaters includes Tina Fey, Stephen Colbert, Tim Meadows and Aidy Bryant. If you stop by one of the city’s many comedy institutions, you’re not only guaranteed a good time, but you may very well see a performance featuring the next star of Saturday Night Live.
The Second City is Chicago’s most famous comedy club, but the smaller clubs are equally, if not more, entertaining and are also significantly cheaper. Venues like IO and The Annoyance Theater often have dozens of shows playing at once and offer more intimate settings. Both theaters have bars with great atmospheres. If you hang around for a beer after a show, you’re sure to run into some of your favorite cast members.
Chicago’s 18-mile 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.
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. If you’ve got time and room in your stomach, why not try them all 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, so pack a picnic and find a boat, rooftop or beach from which to enjoy it.
Along the most central part of the Chicago River, running right through downtown, is a pedestrian walkway stretching just over a mile. It’s a lovely place for a stroll and also offers waterside restaurants and bars, kayak rentals and 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 per person ($89 for children) to have access to five. 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 Historical District. You can also head to the old town for more things to do.
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 Theater 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.
This article is an updated version of a story created by Benjamin Smith.