Events
A Year-Round Guide for 2025
Chicago, the third-largest city in the United States and known as the “Windy City,” is a cultural, architectural, and culinary hub nestled along the shores of Lake Michigan. Famous for its iconic skyline, deep-dish pizza, and vibrant neighborhoods, Chicago offers a rich history and an exciting blend of attractions.
From lively summer festivals to cozy winter holiday markets, Chicago boasts a year-round calendar of events that appeal to visitors of all interests. Whether you’re marveling at world-class art, enjoying live music, or savoring international cuisine, the city’s dynamic energy ensures unforgettable experiences. The months between July and December are especially exciting, as Chicago comes alive with outdoor celebrations in the summer, cultural highlights in the fall, and festive traditions during the holiday season.
January
Chicago Restaurant Week
- Dates: January 24 – February 9, 2025
- Location: Various restaurants citywide
- Contact: info@choosechicago.com
- Special Highlights: Enjoy special prix fixe menus at over 250 of Chicago’s finest dining establishments.
Chicago Sketch Comedy Festival
- Dates: January 9 – 19, 2025
- Location: Stage 773, 1225 W Belmont Ave, Chicago, IL 60657
- Contact: +1 773-327-5252
- Special Highlights: The largest sketch comedy festival in the nation, featuring over 180 shows.
Winter Brew
- Dates: January 25 – 26, 2025
- Location: Lincoln Square, 4700 N Lincoln Ave, Chicago, IL 60625
- Contact: info@lincolnsquare.org
- Special Highlights: A craft beer festival showcasing local breweries in a cozy indoor setting.
February
Chicago Auto Show
- Dates: February 8 – 19, 2025
- Location: McCormick Place, 2301 S King Dr, Chicago, IL 60616
- Contact: info@chicagoautoshow.com
- Special Highlights: The largest auto show in North America, featuring the latest vehicle models and innovations.
Chinese New Year Parade
- Dates: February 10, 2025
- Location: Chinatown, Wentworth Ave and Cermak Rd, Chicago, IL 60616
- Contact: +1 312-326-5320
- Special Highlights: Traditional lion dances, floats, and fireworks celebrating the Lunar New Year.
Chicago Theatre Week
- Dates: February 15 – 25, 2025
- Location: Various theaters citywide
- Contact: info@chicagoplays.com
- Special Highlights: Discounted tickets to over 100 productions, from major theaters to smaller venues.
March
St. Patrick's Day Parade
- Dates: March 16, 2025
- Location: Downtown Chicago, Columbus Dr from Balbo to Monroe St, Chicago, IL 60601
- Contact: info@chicagostpatsparade.com
- Special Highlights: A vibrant parade with bagpipers, dancers, and the iconic dyeing of the Chicago River.
Chicago Flower & Garden Show
- Dates: March 20 – 24, 2025
- Location: Navy Pier, 600 E Grand Ave, Chicago, IL 60611
- Contact: info@chicagoflower.com
- Special Highlights: Stunning garden displays, workshops, and DIY projects for gardening enthusiasts.
International Vintage Poster Fair
- Dates: March 29 – 31, 2025
- Location: Chicago Cultural Center, 78 E Washington St, Chicago, IL 60602
- Contact: info@posterfair.com
- Special Highlights: The largest event in the U.S. dedicated to vintage posters, featuring thousands of pieces from around the world.
April
Chicago Improv Festival
- Dates: April 15 – 21, 2025
- Location: Various theaters citywide
- Contact: info@chicagoimprovfestival.org
- Special Highlights: A week-long celebration of improvisational theater with performances and workshops.
One of a Kind Show
- Dates: April 26 – 28, 2025
- Location: Merchandise Mart, 222 W Merchandise Mart Plaza, Chicago, IL 60654
- Contact: info@oneofakindshow.com
- Special Highlights: Unique handmade goods from artisans and craftspeople across North America.
Art Chicago
- Dates: April 12 – 15, 2025
- Location: Navy Pier, 600 E Grand Ave, Chicago, IL 60611
- Contact: info@artchicago.com
- Special Highlights: Contemporary and modern art fair featuring galleries from around the world.
May
Chicago Kids and Kites Festival
- Dates: May 4, 2025
- Location: Cricket Hill in Lincoln Park, Montrose Ave and Lake Shore Dr, Chicago, IL 60613
- Contact: +1 312-744-3316
- Special Highlights: Free kite-making kits for kids, family-friendly activities, and kite flying demonstrations.
Chicago Mayfest
- Dates: May 17 – 19, 2025
- Location: Lakeview, Ashland Ave and Barry Ave, Chicago, IL 60657
- Contact: info@chicagoevents.com
- Special Highlights: Live music, food, and drinks celebrating the start of the summer festival season.
Chicago House Music Festival
- Dates: May 25, 2025
- Location: Millennium Park, 201 E Randolph St, Chicago, IL 60601
- Contact: info@chicagoparkdistrict.com
- Special Highlights: Free performances by local and international house music artists.
June
Chicago Blues Festival
- Dates: June 7 – 9, 2025
- Location: Millennium Park, 201 E Randolph St, Chicago, IL 60601
- Contact: info@chicagoparkdistrict.com
- Special Highlights: The largest free blues festival in the world, featuring top blues musicians.
Chicago Pride Parade
- Dates: June 30, 2025
- Location: North Side, starting at Montrose Ave and Broadway St, Chicago, IL 60613
- Contact: info@chicagopride.com
- Special Highlights: A vibrant celebration of the LGBTQ+ community with colorful floats and performances.
Grant Park Music Festival
- Dates: June 12 – August 17, 2025
- Location: Jay Pritzker Pavilion, Millennium Park, 201 E Randolph St, Chicago, IL 60601
- Contact: info@grantparkmusicfestival.com
- Special Highlights: Free classical music concerts performed by the Grant Park Orchestra and Chorus.
July
Taste of Chicago
Date: July 10–14, 2025
Contact: info@tasteofchicago.us | (312) 744-3316
Website: www.tasteofchicago.us
Location: Grant Park, 337 E Randolph St, Chicago, IL
Description: One of the world’s largest food festivals, the Taste of Chicago showcases the city’s diverse culinary scene, featuring local restaurants, food trucks, live music, and family activities.
Highlights and Features: Attendees can sample a wide variety of dishes, from deep-dish pizza to international cuisine, while enjoying free concerts on the main stage featuring renowned artists.
Practical Information: Admission to the festival is free, but food and beverages are purchased via tickets available onsite. Public transportation is recommended; Grant Park is accessible via the Red and Blue L lines.
Tips: Visit during weekday afternoons to avoid crowds, and don’t miss the signature “Taste Portions” for smaller, affordable samplings of each vendor’s best dishes.
Windy City Smokeout
Date: July 18–21, 2025
Contact: info@windycitysmokeout.com | (312) 777-4200
Website: www.windycitysmokeout.com
Location: United Center Parking Lot, 1901 W Madison St, Chicago, IL
Description: A four-day festival celebrating country music, barbecue, and craft beer, the Windy City Smokeout is a must-attend summer event for food and music lovers.
Highlights and Features: The festival features performances by top country artists, ribs and brisket from award-winning pitmasters, and over 75 craft beers from local and national breweries.
Practical Information: Tickets range from $50 for single-day general admission to $200 for weekend passes. Limited parking is available; public transit is recommended.
Tips: Arrive early to catch the smaller acts on side stages and explore the vendor booths for exclusive barbecue sauces and merchandise.
Chicago Air and Water Show
Date: July 27–28, 2025
Contact: info@chicagoairandwater.org | (312) 744-3316
Location: North Avenue Beach, 1600 N Lake Shore Dr, Chicago, IL
Description: The Chicago Air and Water Show is among the largest free air shows in the United States, featuring thrilling aerial stunts and watercraft demonstrations over Lake Michigan.
Highlights and Features: Performances include the U.S. Navy Blue Angels, U.S. Army Parachute Team Golden Knights, and other military and civilian pilots.
Practical Information: Admission is free. Spectators can watch from North Avenue Beach or other nearby lakefront spots. Public transit is strongly recommended, as parking is limited.
Tips: Bring sunscreen, folding chairs, and binoculars for the best viewing experience. Arrive early to secure a good spot near the beach.
August
Lollapalooza
Date: August 1–4, 2025
Contact: info@lollapalooza.com | (888) 512-7469
Website: www.lollapalooza.com
Location: Grant Park, 337 E Randolph St, Chicago, IL
Description: One of the world’s premier music festivals, Lollapalooza brings together top artists across multiple genres, including rock, hip-hop, EDM, and pop, for a four-day celebration of music and culture.
Highlights and Features: The festival includes eight stages, over 170 performances, art installations, and a variety of food vendors offering global cuisine.
Practical Information: Tickets range from $150 for single-day passes to $600 for four-day passes. Public transit is recommended, as parking is limited around Grant Park.
Tips: Download the festival app to plan your schedule and navigate the grounds. Stay hydrated and wear comfortable shoes for walking between stages.
Chicago Jazz Festival
Date: August 29–September 1, 2025
Contact: info@chicagojazzfestival.org | (312) 744-3316
Website: www.chicagojazzfestival.org
Location: Millennium Park, 201 E Randolph St, Chicago, IL
Description: The Chicago Jazz Festival celebrates the city’s rich jazz heritage with free performances by local, national, and international artists in Millennium Park and other venues.
Highlights and Features: This year’s lineup includes Grammy-winning artists and emerging talent, with performances taking place at the Jay Pritzker Pavilion and nearby jazz clubs.
Practical Information: Admission is free. Millennium Park is accessible via public transportation, including the Red, Green, and Blue lines.
Tips: Arrive early for main stage performances to secure a good seat, and explore nearby jazz clubs for intimate late-night shows.
Chicago Hot Dog Fest
Date: August 9–11, 2025
Contact: info@chicagohistory.org | (312) 642-4600
Location: Chicago History Museum, 1601 N Clark St, Chicago, IL
Description: A tribute to Chicago’s iconic hot dog, this festival features creative takes on the classic dish, live music, and family-friendly activities.
Highlights and Features: Vendors serve up unique hot dog creations, while historians share the cultural significance of the Chicago-style hot dog.
Practical Information: Admission is free, but food and beverage tickets must be purchased onsite. Parking is limited; public transit is recommended.
Tips: Try hot dogs from multiple vendors to experience the different flavors and styles, and don’t miss the live music performances.
September
Riot Fest
Date: September 13–15, 2025
Contact: info@riotfest.org | (312) 555-1212
Website: www.riotfest.org
Location: Douglass Park, 1401 S Sacramento Dr, Chicago, IL
Description: Riot Fest is a three-day music festival known for its punk, rock, and alternative music lineup, as well as carnival rides and quirky attractions.
Highlights and Features: The festival includes performances by legendary bands, a Ferris wheel, and wrestling matches.
Practical Information: Tickets start at $100 for single-day passes. Public transit or rideshare services are recommended.
Tips: Explore the sideshow attractions and grab a map to navigate the festival grounds.
Oktoberfest Chicago
Date: September 27–29, 2025
Contact: info@oktoberfestchicago.com | (773) 525-2501
Website: www.oktoberfestchicago.com
Location: Lincoln Square, 4700 N Lincoln Ave, Chicago, IL
Description: A traditional German Oktoberfest celebration featuring beer, bratwurst, and live polka music in one of Chicago’s most charming neighborhoods.
Highlights and Features: Authentic German beer, Bavarian pretzels, and live performances by polka bands and folk dancers.
Practical Information: Tickets are $10 for general admission. Public transportation is recommended.
Tips: Dress in traditional German attire for the full experience, and arrive early to secure a spot in the beer garden.
Chicago Gourmet
Date: September 28–29, 2025
Contact: info@chicagogourmet.org | (312) 567-8500
Location: Millennium Park, 201 E Randolph St, Chicago, IL
Description: Chicago Gourmet is a high-end food and wine festival featuring tastings from the city’s top chefs, sommeliers, and mixologists.
Highlights and Features: Guests can enjoy cooking demonstrations, wine tastings, and gourmet dishes from Chicago’s most celebrated restaurants.
Practical Information: Tickets range from $150 to $300. Public transit is strongly recommended.
Tips: Attend the Grand Tasting Pavilion for the widest selection of food and drink options.
October
Chicago Marathon
Date: October 12, 2025
Contact: info@chicagomarathon.com | (312) 904-9800
Website: www.chicagomarathon.com
Location: Start and Finish at Grant Park, 337 E Randolph St, Chicago, IL
Description: The Bank of America Chicago Marathon is one of the six World Marathon Majors, drawing elite athletes and recreational runners from around the globe. The 26.2-mile course takes participants through 29 diverse neighborhoods, showcasing the city’s architecture, culture, and energy.
Highlights and Features: Spectators can enjoy live music and vibrant cheer zones throughout the race route. The event serves as a celebration of community, fitness, and charity, with millions of dollars raised for nonprofit organizations.
Practical Information: Registration is required to participate in the race and typically sells out months in advance. Spectators can line the course free of charge. Public transportation is highly recommended for navigating the city on race day.
Tips: Head to iconic spots like Chinatown or the Loop to cheer on runners while enjoying entertainment and food. If you’re running, arrive early and dress in layers for the cool October morning.
Arts in the Dark Parade
Date: October 19, 2025
Contact: info@artsinthedark.org | (312) 744-3316
Website: www.artsinthedark.org
Location: State Street, Downtown Chicago
Description: The Arts in the Dark Parade is a magical nighttime parade celebrating Chicago’s creative community. It brings together artists, performers, and cultural institutions for a dazzling procession of lights, costumes, and performances.
Highlights and Features: The parade includes illuminated floats, puppets, dancers, and musicians, creating a unique experience that blends Halloween spirit with artistic creativity.
Practical Information: Admission is free. The parade route is accessible via multiple CTA train lines, with stations at Lake, Monroe, and Jackson.
Tips: Arrive early to secure a spot along State Street, and bring a camera to capture the glowing displays. Dress warmly for the evening event.
Open House Chicago
Date: October 26–27, 2025
Contact: info@openhousechicago.org | (312) 922-3432
Location: Various locations across Chicago
Description: Open House Chicago, organized by the Chicago Architecture Center, provides free access to hundreds of the city’s most iconic and unique buildings, many of which are typically closed to the public.
Highlights and Features: Visitors can explore historic mansions, modern skyscrapers, theaters, churches, and cultural landmarks, with expert guides offering insights into Chicago’s architectural history.
Practical Information: Admission is free, but registration is recommended to access the full schedule and building list. Public transportation is the easiest way to visit multiple locations.
Tips: Plan your route ahead of time using the event map, and prioritize locations that are only open during specific hours. Wear comfortable shoes for walking.
November
Thanksgiving Day Parade
Date: November 28, 2025
Contact: info@chicagothanksgivingparade.com | (312) 235-2211
Website: www.chicagothanksgivingparade.com
Location: State Street, Downtown Chicago
Description: The Chicago Thanksgiving Day Parade is a festive tradition featuring larger-than-life balloons, marching bands, floats, and performances from local groups.
Highlights and Features: The parade kicks off the holiday season with appearances by Santa Claus, Broadway-style performances, and multicultural displays.
Practical Information: Admission is free. Spectators can view the parade along State Street between Congress Parkway and Randolph Street. Public transit is highly recommended.
Tips: Dress warmly and arrive early for a good viewing spot. Bring a thermos of hot coffee or cocoa to stay warm.
Magnificent Mile Lights Festival
Date: November 23–24, 2025
Contact: info@lightsfestival.org | (312) 409-5560
Website: www.themagnificentmile.com/lights-festival
Location: Michigan Avenue, Magnificent Mile
Description: The Magnificent Mile Lights Festival kicks off the holiday season in Chicago with a dazzling parade, live music, and the illumination of over one million lights along Michigan Avenue.
Highlights and Features: The two-day festival includes family-friendly activities, an evening tree-lighting parade featuring Mickey Mouse, and a spectacular fireworks display over the Chicago River.
Practical Information: Admission is free. The event is accessible via CTA buses and trains, with multiple stops along Michigan Avenue.
Tips: Arrive early for the best viewing spots along the parade route, and dress warmly for the chilly November weather.
Christkindlmarket
Date: November 22–December 24, 2025
Contact: info@christkindlmarket.com | (312) 494-2175
Website: www.christkindlmarket.com
Location: Daley Plaza, 50 W Washington St, Chicago, IL
Description: Inspired by traditional German holiday markets, Christkindlmarket Chicago is a beloved holiday tradition featuring festive stalls selling ornaments, gifts, and European treats.
Highlights and Features: Visitors can enjoy mulled wine in souvenir mugs, authentic German bratwurst, and handmade goods from international vendors. A life-sized Christmas pyramid and live holiday music add to the festive atmosphere.
Practical Information: Admission is free. Daley Plaza is easily accessible via public transit, including the Red and Blue lines.
Tips: Visit during weekday mornings to avoid crowds, and bring cash, as some vendors do not accept cards.
December
ZooLights at Lincoln Park Zoo
Date: December 1–31, 2025 (select evenings)
Contact: events@lpzoo.org | (312) 742-2000
Website: www.lpzoo.org
Location: Lincoln Park Zoo, 2001 N Clark St, Chicago, IL
Description: ZooLights transforms Lincoln Park Zoo into a winter wonderland with spectacular light displays, holiday-themed activities, and seasonal treats.
Highlights and Features: Visitors can enjoy ice carving demonstrations, photos with Santa, and hot cocoa while strolling through the illuminated zoo grounds.
Practical Information: Admission is free, but some activities require tickets. Parking is available for a fee; public transit is recommended.
Tips: Visit early in the evening for smaller crowds, and bundle up for the outdoor event.
Ice Skating at Millennium Park
Date: December 1, 2025–March 1, 2026
Contact: info@millenniumpark.org | (312) 742-1168
Website: www.millenniumpark.org
Location: McCormick Tribune Ice Rink, Millennium Park, 201 E Randolph St, Chicago, IL
Description: Ice skating at Millennium Park is a quintessential Chicago winter experience, offering stunning views of the city skyline and the iconic “Bean.”
Highlights and Features: Skaters of all ages can enjoy the festive atmosphere while gliding across the rink. Skate rentals and hot cocoa are available onsite.
Practical Information: Admission is free, but skate rentals cost $15. The rink is accessible via public transit.
Tips: Weekday mornings are less crowded. Dress in layers and bring gloves for comfort.
New Year’s Eve Fireworks at Navy Pier
Date: December 31, 2025
Contact: info@navypier.org | (312) 595-7437
Website: www.navypier.org
Location: Navy Pier, 600 E Grand Ave, Chicago, IL
Description: Ring in the new year with a dazzling fireworks display over Lake Michigan at Navy Pier. The event includes live entertainment, dining options, and festive activities leading up to the countdown.
Highlights and Features: The fireworks are synchronized to music, creating a breathtaking display of color and sound. Indoor events at Navy Pier include family-friendly activities and live performances.
Practical Information: Admission to the pier is free, but reservations are required for some restaurants and events. Public transit or rideshare services are recommended, as parking fills up quickly.
Tips: Arrive early to explore Navy Pier’s attractions before the fireworks. Dress warmly for the outdoor show, and secure a spot by the lake for the best view.
Tickets and Booking
- Online: Most events have online ticket sales on their official websites.
- On-Site: Some events offer on-site ticket sales.
- Prices: Vary by event, with options ranging from free to several hundred dollars for premium experiences.
Getting There
- Public Transportation: Chicago Transit Authority (CTA) offers buses and trains that service most event locations.
- Parking: Available at most venues but can be expensive; public transit is often more convenient.
- Accessibility: Most events and venues are accessible to people with disabilities.
- Nearby Hotels: Book early for major events as hotels can fill up quickly.
- Recommendations: Look for hotels near event venues for convenience.
Insider Tips
Best Times to Attend:
- Early Arrival: Arrive early to avoid crowds and secure the best spots.
- Weekdays: Often less crowded than weekends.
Local Customs:
- Respectful Behavior: Be mindful of local customs and respectful during parades and festivals.
Additional Attractions:
- Explore Nearby: Check out local attractions like museums, parks, and restaurants while attending events.
Safety and Comfort
Staying Safe:
- Crowds: Stay aware of your surroundings in crowded areas.
- Weather: Dress appropriately for the weather; Chicago can be cold in winter and hot in summer.
Comfort Tips:
- Essentials: Bring water, snacks, and sun protection for outdoor events.
- Layering: Dress in layers for fluctuating temperatures.
Planning Your Visit
Chicago offers a wealth of events throughout the year, making it a vibrant destination for visitors. From food festivals to music events and cultural celebrations, there’s always something happening in the Windy City. Plan your visit around these exciting events to experience the best of what Chicago has to offer. Happy exploring!