With 2026 underway, we’re excited for all our upcoming trips this year. But globetrotting aside, our own city of Chicago offers enough adventures to fill a whole calendar. We love being tourists in our own backyard, exploring it even after decades of living there. And because we are always obsessed with underrated attractions, we want to share our favorite activities in the city and suburbs that may not be too obvious. Consider this our month-by-month off-the-beaten-path travel guide of Chicago.
January
Anyone who visits Chicago in January deserves a medal for bravery. Whenever we hear someone planning a trip to Chicago in January, we try to talk them out of it. It’s brutal here. The holidays are over, the lake is frozen, and the city seems to be hibernating. Not surprisingly, the best activities are indoors: whether exploring Chicago’s blues scene or going for pizza and rating which joint has the best deep dish. To escape the cold, one of our favorite activities is visiting a spa. And not just to any spa, but a Korean spa.
Located in suburban Niles, just north of Chicago, King Spa & Sauna represents a tradition of Korean spas known as jjimjilbang. Open 24/7, this mega spa complex is the largest Asian sauna in the United States and offers a unique cultural experience of communal bathing and relaxation. The wet areas of the spa are gender-segregated and feature tubs and whirlpools, steam rooms, and traditional services like massages and body scrubs. The co-ed space, where you wear comfy pajamas provided by the spa, includes multiple dry sauna rooms, such as the Salt Room, the Ocher Room, the Charcoal Room, the Amethyst Room, a movie theater, and a Korean restaurant. It’s a great spot for relaxation.
Tip: H Mart, a popular Asian supermarket, is right next door and there, at the service counter, you can buy discounted tickets to the spa.
February
The weather is still miserable in Chi-Town, and the collective morale sinks to its lowest point with many residents contemplating whether it’s time to move somewhere warmer. As winter’s freezing grip continues, we still spend most of our time inside. February has become our “theater” month, when we go to performances almost every weekend. Chicago’s theater scene is impressive. Almost every night, dozens of local theaters, as well as touring companies, stage high-quality productions. Goodman, Steppenwolf, Lookingglass, Court, Raven, and many others—the quality and the quantity of theatre is top-notch. Some shows that get started in Chicago sometimes even end up in New York. Just two years ago, we were lucky to see Steppenwolf’s Purpose, which later transferred to Broadway, where it received critical acclaim and won the Tony Award for Best Play. Grab your tickets and enjoy a show. Check hottix.org for discounted tickets.
If you are courageous enough for outside activities, each February, Chinatown hosts Chinese New Year celebrations. Dress warmly and enjoy the parade, which usually features colorful floats, dancing dragons and lions, and shivering local politicians. After the parade, warm up with hot steamed dumplings or a bowl of Sichuan soup at one of Chinatown’s restaurants.
March
The days can still be frigid, but the city finally starts waking up from winter’s hibernation. For a lot of Chicagoans, an unofficial end of winter is St. Patrick’s Day, when the Chicago River is dyed green and life somewhat returns to normalcy. For us, the best attractions are still indoors. In March, both the Lincoln Park Conservatory and the Garfield Park Conservatory host spring shows, featuring an astonishing display of daffodils, tulips, and hydrangeas that fill the spaces. Although the city streets may still be covered in snow, blooming spring flowers unmistakably signal that the end of brutal winter is just around the corner.
April
Ukrainian Village is one of the oldest and most underrated neighborhoods in the city. Home to several Ukrainian churches, two Ukrainian museums, and many Ukrainian-owned businesses, the neighborhood has long been home to a sizeable Ukrainian diaspora. One of our favorite events in the city is the egg-painting workshop that takes place every year shortly before Easter at the Ukrainian National Museum. A pagan custom that later became a part of Christian Orthodox Easter celebrations, egg painting is a form of Ukrainian folk art. The workshop is a great place to create an exquisitely painted Easter egg, learn more about the Ukrainian culture and traditions, and visit the museum. Julia has been going to these workshops for years, and our apartment is now filled with beautifully painted Easter eggs. We usually cap our visit by eating lunch at the nearby Trizub restaurant serving modern Ukrainian fare and loading up on Ukrainian grocery items at Ann’s Bakery and Goods across the street.
May
The Magnificent Mile is a popular Chicago attraction and well worth visiting, especially for those seeking an upscale shopping experience. But in early May, this section of Michigan Avenue truly lives up to its name. For several weeks, it dazzles and wows visitors with thousands of blooming tulips of different colors, shapes, and sizes. Just stroll along the iconic street and enjoy the show. A truly not-to-miss experience!
June
The classic summer activity in the Windy City is catching a baseball game. Chicago is a great baseball town and home to two major league teams with an illustrious history. And while both the Cubs and the White Sox get you the MLB experience, a Chicago Dogs game in Rosemont by O’Hare Airport is also worth checking out. Although the Dogs play in an independent baseball league, and the quality of baseball is much lower than in the majors, the cozy ballpark and a fun atmosphere make up for it. Named after the famous Chicago hot dogs, the team has one of the best names and logos in professional sports (Milwaukee Milkmen from the same baseball league come in a close second). The fan entertainment at Impact Field is always good. Two antagonistic mascots, Mustard and Ketchup, keep the atmosphere at the ballpark fun and light. On Saturdays, there are fireworks after the game. Our favorite day is Family Sunday, when fans are allowed to throw a baseball on the field and get autographs from the entire team before the game.
July
Although the “City of Festivals” nickname belongs to the nearby Milwaukee, there are plenty of festivals in Chicago. One of our favorites is the Colombian Fest that usually takes place around July 20, Colombia’s Independence Day. The location of the festival changes from year to year, but the constant is the abundance of Colombian music —from salsa to cumbia —and Colombian foods, such as arepas, buñuelos, and fried plantains. The festival runs for three days (from Friday to Sunday), and Friday is typically free of charge and honors Chicago’s first responders and fallen police officers.
August
Not many people consider Chicago a beach destination. But for several weeks in the summer, the city may surprise you. In August, Lake Michigan finally warms up, and under the right weather conditions, the water appears almost Caribbean turquoise blue. The action on the beach, in the shadow of skyscrapers, is also strong, with people sunbathing, swimming, picnicking, and playing volleyball. On weekends, the golden sands of Chicago’s beaches are full of people and energy, at times resembling Rio’s Copacabana beaches. When I took my parents to North Street Beach during their visit to Chicago, they were pleasantly surprised by the quality of the beach and wondered why I didn’t spend more time there in the summer with such an incredible place so close to home.
September
While Chicago’s winters are harsh and summers can bring scorching heat, September is one of the best months to take a walk around the city. Our favorite neighborhood for walking is Oak Park, west of downtown. With its broad, tree-lined streets and buildings designed by Frank Lloyd Wright and his contemporaries, strolling through the neighborhood is always a pleasurable and meditative experience. The Frank Lloyd Wright Home and Studio is the most logical place to begin your exploration. From here, you can either take a guided tour with one of the museum’s docents or get a map of the area and do a self-guided walk at your own pace.
October
Every January, when we sketch out our activities for the year, we block off one particular weekend in October on our calendars—Open House Chicago. Organized by the Chicago Architecture Center, this event provides a unique opportunity to get inside some of the iconic buildings that are otherwise closed to the public. For out-of-town tourists, Open House Chicago is great because it allows them to see the city from the top floors of many buildings for free and save money on admission prices to observation decks, such as Willis Tower ($32) or the former John Hancock Center ($30). The event covers not only downtown but also many of the other 77 Chicago communities. Although the emphasis is primarily on architecture, the event also allows you to discover more about local businesses, such as glassblowing studios, bowling alleys, and breweries and distilleries. Exploring Chicago’s neighborhoods during beautiful fall foliage is also why we try to make the event every year.
November
We already wrote about this event in a different post, but Chicago has one of the best Day of the Dead celebrations. This ancient Mexican holiday is widely celebrated in Pilsen, a predominantly Mexican neighborhood. The decorations are up, and local bakeries sell delicious pan de muerto. The National Museum of Mexican Art hosts the temporary exhibit dedicated to the holiday, and for one evening, colorful ofrendas are set up by the museum, and the community celebrates the lives of departed loved ones. You can even buy cempasúchil (marigolds), the yellow flower closely associated with this holiday, in the neighborhood.
December
For many people, December bucket list items in Chicago include visiting the German-style Christkindlmarket at Daley Plaza and ice-skating in Millennium Park by the Bean. We are not here to persuade you that it’s a bad way to spend time in the city (although do prepare for crowds). But suburban Rosemont, right across from the Chicago Dogs stadium, gets quite festive, too. A Christmas tree, holiday decorations, and an ice-skating rink—the place is fun and filled with holiday cheer without the downtown crowds and expensive parking.
So, there you have it! Our own travel guide of hidden gems in Chicago. Enjoy it and say hello if you run into us while exploring our favorite city.
