The Best Things To Do Around Chicago On A Rainy Day, According To Tripadvisor Reviews

Chicago earns its moniker of the Windy City honestly, and with winds often come rain. Chicago averages 37 inches of rain per year, with some rain falling 133 days out of the average year. In other words, the chances are high that you're going to encounter some rain on your visit. This doesn't have to leave you moping in your hotel room, as the city is brimming with indoor activities. Chicago is one of the top-rated cities in the country for museums, there is no shortage of architecturally stunning buildings to tour, and Chicago's great steakhouses and pizzerias are unparalleled. After dinner, theater lovers can then find some of the country's edgiest and most forward-thinking work created in the country.

Since there are so many indoor attractions to choose from — and to help inform our own advice for decision-making — we also turned to traveler rankings on Tripadvisor of the best things to do on a rainy day to help you spend those foul-weather days in a memorable fashion. These travelers listed many options, including some of Chicago's underrated tourist attractions. So, grab your umbrella and rain slicker. Let's explore the third-largest city in the U.S.

Once you've scratched the major museums off your bucket list, there is no shortage of smaller museums that visitors call out as some of Chicago's best indoor destinations. The ones that top the list of Chicago travelers include the Richard Driehaus Museum, the Medieval Torture Museum, the Chicago History Museum, the American Writers Museum, and the Institute for the Study of Ancient Cultures.

The Richard Driehaus Museum is a delight for all who revel in the architecture of the Gilded Age. Within its walls, you'll find works by Tiffany Studios, cabinetry from the late 1800s, and Low Art Tile Works. The Medieval Torture Museum takes a more gruesome turn as it challenges visitors to have the courage to face the cruelties of the past. It was the country's first torture museum. It asks people to discover whether they would be the tormentor or the tormented and to avoid repeating the sins of the past. 

The Chicago History Museum celebrates all that has made the Windy City the colorful bastion, from the Great Chicago fire to its mobster past to the culturally diverse settlers of individual neighborhoods. The American Writers Museum is an interactive destination that celebrates all genres of American writing. And if the rain is pouring too hard to keep you from leaving your hotel room, they have virtual exhibits. Once called The Oriental Museum, the University of Chicago's Institute for the Study of Ancient Cultures has galleries and exhibits spanning 10,000 years of human history. 

Rain or shine, the United Center is the place to go for fans of the Chicago Bulls basketball team or the Chicago Blackhawks hockey team. The owners of those two teams got together in 1988 to build the largest arena in the U.S. In 1994, they cut ribbons to open it, and since then, it has hosted more than 200 events per year. In addition to the basketball and hockey games, major musical stars host their concerts there including Madonna, The Rolling Stones, U2, The Who, and Bruce Springsteen. The United Center has hosted the Democratic National Convention, music festivals, Disney on Ice, college basketball tournaments, and the circus.

Bulls fans will want to make sure they visit the new United Center atrium where they can take in the Michael Jordan statue. Meanwhile, anyone with family members on the spectrum will be relieved to know there is a sensory room, a therapeutic space designed to provide a calming environment for those with sensory sensitivities. Head to the guest relations booth at Gate 2 to request access to this quiet space. Note that when you go, United Arena is a fully cashless arena, so take a debit or credit or have Google Pay/Apple Pay set up on your phone. 

Outside of Broadway, Chicago is one of the top U.S. destinations for theater lovers, which is how it got its tongue-in-cheek nickname in the theater world of being the Second City, the same name that the famous improv troupe claimed. Chicago has more than 250 theater companies — five of which have won Tonys. There is almost always a show to see somewhere. Some visitor favorites include The Chicago Theatre, Lookingglass Theatre Company, The Lyric Opera of Chicago, the James M. Nederlander Theatre, and Chicago Shakespeare on Navy Pier.

What makes Chicago special as a theater destination? It is the birthplace of storefront theater and improv comedy. Some of the biggest names in theater, including David Mamet, Tina Fey, Laurie Metcalf, Stephen Colbert, Tracy Letts, and Martyna Majok, got their start in Chicago. The city claims it has more world premieres than any other city in the country. The diversity in shows and locales is part of what makes Chicago such an enticing theater destination. There are the old, architecturally grand theaters downtown and others hidden away in church basements or small storefronts. 

You can catch a Broadway musical or an intimate one-person experimental show. On any given day, you can find classics, avant-garde works, and a wide range of dramas, comedies, and family shows. Chicago Plays offers an online aggregate guide to theater in the city.

Reeling from the Great Fire of 1871, Chicago set out to rebuild and quickly became the playground of architects. They pioneered steel-frame construction for skyscrapers and the city competed with New York City in the early 20th century to be the city of skyscrapers. But not all its famous buildings are skyscrapers. Chicago proudly boasts a connection with one of America's imminent architects, Frank Lloyd Wright, who apprenticed in the Windy City and opened his own practice in 1893 from where his fame would grow.

When looking for a rainy day activity, visitors recommend two buildings Wright was intimately involved in: the Rookery Building and the Frank Lloyd Wright Robie House. The Frank Lloyd Wright Trust arranges tours for both buildings. The Rookery Building pre-dates Wright, originally an 11-story business building (a 12th floor was later added) designed by Daniel Burnham and John Root and completed in 1888. Wright led its renovation in 1905 where he encased the iron columns in gilded white marble and added bronze chandeliers to the light court. Thirty years later, William Drummond would add an art deco look and replace Wright's open-geometric elevator cages with solid bronze doors etched with birds. It is now on the National Register of Historic Places and one of Chicago's official landmarks. 

The Robie House is one of the best examples of Wright's famous Prairie style and is considered one of the most innovative and important buildings in architectural history. Built in 1910, it kicked off the modernist movement for residential homes. It's a home where every element is interconnected from the grounds and the building to the furniture and ornamentation. While three families lived in the home as a residence, it would go on to become a classroom, a refectory, a dormitory, and office spaces before becoming the museum that it is today. Both guided and self-guided audio tours are available of the home.

The city is filled with incredible dining, from famous steakhouses to Chicago-style pizzerias and everything in between. But if you ask Tripadvisor reviewers, for the best place to eat and drink on a rainy day, they'll tell you Goose Island Beer Co. There are three locations appealing to craft beer lovers: a brewhouse, a barrel house, and an events space. Whether you are going there for a meal, a brew, or a tour, it's a chance to experience the beer that sparked the craft beer revolution in the U.S. They exist, they say, "to lead in the craft of brewing by creating award-winning beers that define classic and innovative styles to capture the hearts, imaginations, and palates of beer drinkers."

Goose Island Beer was founded after the founder, John Hall, took a tour across Europe and was impressed with how many different types of beer there were in each region. He decided that America needed to have its own craft brewing culture. This was in 1988, and after Hall figured out how to make great beer, he invited people in to watch how he did it. In 1995, he opened a larger brewery with another brewpub to follow in 1999. 

In 2011, Anheuser-Busch acquired Goose Island Beer Company. You can tour the 1995 brewery, which creates brews using 32 fermenters and more than 15 different types of yeast systems. The Goose Island Barrel House is home to their bourbon barrel-aged beers, a process they pioneered. The Clybourn Brewhouse, which opened in 1988, closed in December 2023 but with a new location: Goose Island at the Salt Shed is to open in 2024.

What better way to spend a rainy day than curled up with a book? Perhaps that's why Tripadvisor reviewers suggest a visit to the Harold Washington Library Center, Chicago Public Library's main library located in the South Loop and named for Chicago's first Black mayor. It was that mayor, Harold Washington, who first launched the design/build competition for the library in 1987 with a $144 million bond issued to pay for it. The winner was Thomas Beeby from Hammond, Beeby & Babka, Inc. The design is an example of late 20th Century American Architecture and elements throughout the building pay homage to Chicago's history and culture. 

When you go, search out the five massive stone owls that fly atop the library. A 20-foot-high, three-ton great horned owl is over the building's entrance while the other four 12-foot-high barn owls perch on the corners of the building's roof. On the ninth floor, you can spend a rainy day touring their winter garden. Other highlights are the special collections, genealogy databases and the Ancestry Library edition, a newspaper microfilm collection, original artwork by more than 50 artists, author events, a Maker Lab, and free music practice rooms with pianos and more than 40,000 volumes of printed music. Browsing the shelves is a great way to stay dry on Chicago's rainy days.