Chicago Events & Things to Do: Architecture, Millennium Park, Sports, Comedy & Concerts

Quick answer: The best things to do in Chicago include catching a Cubs game at Wrigley Field or a White Sox game at Rate Field, taking an architecture river cruise, seeing Cloud Gate ("The Bean") in Millennium Park, stepping onto The Ledge at Skydeck Chicago, eating deep-dish pizza, and exploring world-class museums. Summer brings baseball, Lollapalooza, and lakefront fun. Fall and the holidays bring the Chicago Marathon, the Magnificent Mile Lights Festival, and Christkindlmarket.

Looking for things to do in Chicago this weekend, today, or with kids? Chicago is famous for its skyline, best seen on an architecture river cruise, plus Millennium Park and Cloud Gate, Navy Pier, the Art Institute of Chicago, and deep-dish pizza. It's one of America's great sports towns with the Cubs, White Sox, Bears, Bulls, and Blackhawks, and nightlife runs from Second City comedy to late-night blues clubs.

What Is There to Do in Chicago?

Chicago offers something for every type of traveler. All year long, visitors can find pro sports, concerts, festivals, comedy shows, theater, food and drink experiences, river and lake cruises, sightseeing tours, museums, and family activities across the city.

Want to know what's happening during your visit? Explore our listings to find upcoming events and experiences for your travel dates.

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What Baseball Teams Are in Chicago?

Chicago is one of the few cities with two Major League Baseball teams: the Chicago Cubs on the North Side and the Chicago White Sox on the South Side. The rivalry between the two fan bases is one of the best in sports, and a game at either ballpark is a must for any baseball fan.

In 2026, both teams made the postseason in the same year. The Cubs clinched a Wild Card berth for their second straight playoff appearance. The White Sox clinched a playoff spot after three straight 100-loss seasons, becoming the first team ever to reach the playoffs after back-to-back 100-loss seasons.

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Chicago Cubs Games at Wrigley Field

Wrigley Field opened in 1914, making it the second-oldest ballpark in the majors, behind only Boston's Fenway Park. It's famous for its ivy-covered outfield walls, hand-turned scoreboard, rooftop seats, and the classic red marquee at Clark and Addison.

The surrounding Wrigleyville neighborhood is packed with sports bars and restaurants, and Gallagher Way next to the ballpark hosts events all year. Even when the Cubs aren't playing, you can book an official Wrigley Field tour to go behind the scenes.

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Chicago White Sox Games at Rate Field

The White Sox play at Rate Field on the South Side. Formerly known as U.S. Cellular Field and Guaranteed Rate Field, it has been the home of the White Sox since 1991.

Sox games are known for their loyal, hard-working South Side fan base, great tailgating in the parking lots, and easy access from downtown on the CTA Red Line. The 2026 postseason run made it one of the most exciting times to be a Sox fan in years.

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When Is Baseball Season in Chicago?

The MLB regular season runs from late March through late September, with the postseason in October. The 2027 season is set to begin with Opening Day on Thursday, March 25, 2027.

Each summer, the Cubs and White Sox also face off in the Crosstown Classic, one of the most anticipated series of the year in Chicago. In 2026, the series wrapped up with a three-game set at Wrigley Field in August.

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More Chicago Sports: Bears, Bulls, Blackhawks & More

Baseball is only the start. Chicago is a true pro sports city:

• Chicago Bears: NFL football at Soldier Field on the lakefront.
• Chicago Bulls and Chicago Blackhawks: NBA basketball and NHL hockey at the United Center.
• Chicago Sky and Chicago Fire: WNBA basketball and MLS soccer.
• Chicago Marathon: One of the world's major marathons. The 48th running is Sunday, October 11, 2026.

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What Are the Best Things to See in Chicago?

• Architecture River Cruise: Chicago is famous for its skyline. The Chicago Architecture Center river cruise is one of the most popular ways to see it, running March through November.
• Cloud Gate ("The Bean"): The giant mirrored sculpture in Millennium Park measures 66 feet long and 33 feet high.
• Skydeck Chicago: Step onto The Ledge, glass boxes that extend 4.3 feet out from the Willis Tower.
• The Art Institute of Chicago: Founded in 1879, it's one of the world's major art museums.
• Navy Pier: Rides, restaurants, boat tours, and fireworks on Lake Michigan.

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Upcoming Chicago Events in 2026 and 2027

Chicago's event calendar is full year-round:

• Chicago Marathon: October 11, 2026, one of the six World Marathon Majors.
• Magnificent Mile Lights Festival: The 35th annual kickoff to the holiday season, with a parade and fireworks on the river, is Saturday, November 21, 2026.
• Christkindlmarket: Chicago's German-style holiday market opens November 20, 2026, in the Loop through December 24 and in Wrigleyville through December 31.
• Lollapalooza: The famous four-day music festival returns to Grant Park July 29 to August 1, 2027.

Hotels fill up fast during these weekends, so book tickets and lodging early.

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Where Should You Eat in Chicago?

Chicago is one of the best food cities in the country. It's famous for deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, Garrett popcorn, and an award-winning restaurant scene.

A guided food tour is one of the easiest ways to try several Chicago classics in one afternoon.

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Chicago Comedy, Theater & Live Music

Chicago is a legendary live-entertainment city. It's known for improv and sketch comedy, a thriving theater district, and deep roots in blues and jazz. Big concert tours regularly play the United Center, Soldier Field, and Wrigley Field.

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Things to Do in Chicago With Kids

Traveling with kids? Chicago has plenty of family-friendly attractions and activities, including Navy Pier, the Field Museum, the Shedd Aquarium, the Museum of Science and Industry, Lincoln Park Zoo, Millennium Park, Skydeck Chicago, and Cubs and White Sox games.

Families can mix museums, lakefront fun, and live sports to build a trip everyone will enjoy.

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Free Things to Do in Chicago

• Millennium Park: Cloud Gate, Crown Fountain, and free summer concerts at Pritzker Pavilion.
• Lincoln Park Zoo: One of the last free zoos in the country.
• Chicago Lakefront Trail: 18 miles of lakefront path with beaches and skyline views.
• Navy Pier: Free to walk, with summer fireworks and lake views.

Things to Do in Chicago for Adults & Couples

• Architecture river cruise: The top-rated way to see Chicago's skyline.
• Second City comedy: The improv theater that launched generations of comedians.
• Live blues: Kingston Mines and Buddy Guy's Legends.
• Skydeck or 360 Chicago: Sky-high views at sunset.

Things to Do in Chicago This Weekend & Today

Chicago weekends in summer mean street festivals, beaches, and baseball at Wrigley. In the colder months, plan around museums, comedy, and Bulls or Blackhawks games at the United Center.

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Popular Chicago Questions

What are the best free things to do in Chicago?

Free favorites in Chicago include Millennium Park, Lincoln Park Zoo, Chicago Lakefront Trail, and Navy Pier. See the free things to do section above for details.

What are the best things to do in Chicago for adults and couples?

Popular picks for adults and couples in Chicago include architecture river cruise, Second City comedy, live blues, and Skydeck or 360 Chicago.

What MLB teams play in Chicago?

Chicago has two MLB teams. The Chicago Cubs (National League) play at Wrigley Field on the North Side, and the Chicago White Sox (American League) play at Rate Field on the South Side.

How old is Wrigley Field?

Wrigley Field opened in 1914. That makes it the second-oldest ballpark in Major League Baseball, behind Fenway Park in Boston.

Can you tour Wrigley Field?

Yes. The Cubs offer official Wrigley Field tours, with stops that typically include the dugouts, the press box, and field-level views of the ivy.

When is Opening Day 2027 for the Cubs and White Sox?

MLB's traditional Opening Day for 2027 is Thursday, March 25, 2027. Check each team's schedule for its first home game.

When is the Chicago Marathon 2026?

The 2026 Bank of America Chicago Marathon is Sunday, October 11, 2026.

When is the best time to visit Chicago?

Late spring through early fall (May to October) brings baseball season, festivals, lakefront beaches, and river cruises. November and December are great for holiday events like the Magnificent Mile Lights Festival and Christkindlmarket. Winters are cold, but hotel prices are often lower.

What is there to do in Chicago this weekend?

Browse Chicago tours and activities for architecture cruises, food tours, and experiences you can book for your dates.

Plan Your Chicago Trip

Chicago is a city you can experience differently every time you visit. Cheer on the Cubs at Wrigley Field or the White Sox at Rate Field, cruise the river past world-famous architecture, snap a photo at The Bean, dig into deep-dish pizza, catch a comedy show, or celebrate the holidays on the Magnificent Mile.

Start exploring Chicago with Get Your Ticket and discover your next game, event, tour, or adventure.

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