If you’re like me, planning is non-negotiable, especially when your calendar is filling up with the best and most exciting Chicago events 2026 has to offer.
Whether you’re hosting friends during the summer, spending the holidays with family, or enjoying the city solo, this curated list has you covered year-round. With so much happening across Chicago, it’s easy to let time slip by and miss your favorite annual events.
Let The Haute Seeker’s Guide to Chicago Events 2026 be your go-to planning resource, helping you make the most of the city with curiosity and less stress.
Chicago Events & Experiences 2026
1. Chicago Restaurant Week
Dates: January 23 – February 8, 2026
Locations: Citywide
Price: $30 – $60
Chicago Restaurant Week kicks off the year with one of the city’s most anticipated food events. This is one of my favorite events of the year as it allows me to check out some of the hottest(and even hardest to get into) restaurants around Chicago. It’s also a great time to discover new restaurants in the city and the surrounding suburbs. This is because hundreds of restaurants across dozens of neighborhoods offer special prix fixe menus, making this one of the best times to explore Chicago’s dining scene without peak-season prices.
2. Chicago Theatre Week
Dates: February 5 – February 15, 2026
Locations: Citywide
Price: $15 – $30(or less)
Chicago Theatre Week gives arts lovers discounted tickets to over 100 performances citywide, from intimate theaters to large stages. Tickets go on sale January 6, 2026, through the League of Chicago Theatre and Choose Chicago.
Haute Tip: Looking for discounts at Chicago theaters all year long? Check out TodayTix It’s where I find discounted shows to my favorite venues throughout the year.
3. Chicago Auto Show
Dates: February 7 – February 16, 2026
Location: McCormick Place | South Loop
Price: $0 – $24.34
The 118th Chicago Auto Show showcases the latest vehicles, indoor test tracks, and outdoor ride-and-drives. New for 2026, Chi-Town Alley celebrates Chicago car culture with custom builds and performance rides. Returning favorites for this exciting Chicago event include VIP Tours, Automotive Career Day, and the Family Zone. Tickets are now on sale at ChicagoAutoShow.com.
4. St. Patrick’s Day Parade
Date: March 14, 2026
Location: Downtown Chicago
Price: Free Entry
The unofficially official start of spring commences with St. Patrick’s Day in Chicago and the dyeing of the Chicago River. The St. Patrick’s Day Parade in downtown Chicago features festive floats, lively Irish music, and, of course, the famous dyeing of the Chicago River. Perfect for families and friends, this free event is a beloved city tradition that celebrates the refreshing spring. Be sure to save this celebratory, iconic outdoor event in your calendar.
5.2026 NCAA MARCH MADNESS Midwest Regional
Dates: March 27 & March 29, 2026
Location: United Center | Near West Side
Price: $380 – $8,000
College basketball fans in Chicago can enjoy March Madness in their backyard this year. In 2026, Chicago hosts the NCAA Men’s Basketball Midwest Regional, bringing tournament energy and national attention to the United Center.
6.C2E2 (Chicago Comic & Entertainment Expo)
Dates: March 27 – 29, 2026
Location: McCormick Place | South Loop
Price: $25 – $375
Fans of pop culture, comic enthusiasts, collectors, cosplayer lovers, and more come together each spring for C2E2. This entertainment convention and expo features panels, interactive content, celebrities, and more for a weekend of exciting fandom experiences. From comics to gaming, this is one of the top things to do during the spring in Chicago.
7. EXPO Chicago
Dates: April 9–12, 2026
Location: Navy Pier | Streeterville
Price: TBD
EXPO Chicago is the city’s premier contemporary art fair and one of the most culturally significant Chicago events in spring 2026. Hosted at Navy Pier, this internationally recognized event features global galleries, large-scale installations, artist talks, and citywide programming. As an art lover, I always look forward to this event. It’s a great weekend of thought-provoking pieces and great conversations. I always look forward to the gallery open house events in different neighborhoods—go for the art, stay for the free wine and snacks!
Haute Tip: Many events offer early-bird tickets and season passes. Set calendar reminders a few months ahead for the best deals.
8. Chicago Farmers’ Markets
Dates: May – October 2026
Locations: Citywide
Price: Free Entry
Chicago farmers’ markets are truly a warm-weather staple in the city. Enjoy fresh produce and goods and produce at one of Chicago’s city farmers’ markets. Farmers’ markets occur daily throughout various Chicago neighborhoods and are free to attend.
9. Summer Saturday Fireworks at Navy Pier
Dates: May – August 2026
Location: Navy Pier | Streeterville
Price: Free Entry
Make your summer nights just a little bit brighter with free Saturday fireworks at Navy Pier. This outdoor event is a family-friendly favorite and one of the best things to do in Chicago this year.
10. Pokémon Fossil Museum Exhibition
Dates: May 22, 2026 – April 11, 2027
Location: The Field Museum
Price: Ticketed plus Museum Admission
This immersive museum exhibition makes its North American debut at the Field Museum in Chicago, blending real fossils with fossil Pokémon models and exploration learning that’s perfect for kids, families, and pop culture fans alike.
11. Savannah Bananas at Wrigley Field
Dates: July 24, 2026 – July 26th, 2026
Location: The Field Museum
Price: Ticketed plus Museum Admission
The Savannah Bananas bring their wildly popular Banana Ball experience to Chicago, making this one of the most bucket-list Chicago sports events of 2026. Hosted at historic Wrigley Field, this high-energy, entertainment-first baseball experience blends sports, performance, and spectacle.
12. WNBA AT&T All-Star Game
Date: July 25, 2026
Location: United Center
Price: TBD
Chicago hosts the WNBA All-Star Game, spotlighting the league’s top talent in women’s basketball and bringing major summer sports energy to the city of Chicago. Besides the game, fans will enjoy a multi-day lineup of events and activations across the city, including:
- Community impact events highlighting the WNBA’s commitment to youth engagement around Chicago and at the Sky’s brand-new practice facility in Bedford Park.
- The 3-Point Contest and Kia WNBA Skills Challenge will take place on Friday, July 24, at Wintrust Arena, home of the Chicago Sky.
- WNBA Live, the league’s interactive fan festival featuring player appearances, performances, and celebrating the WNBA’s intersection with fashion, music, and culture, will take place at McCormick Place.
13. Opening of the Obama Presidential Library
Dates: Summer 2026
Location: Obama Presidential Library | Woodlawn
Price: TBD
The opening of the Obama Presidential Library marks one of the most important Chicago cultural events of 2026. This long-anticipated destination will serve as a global center for history, education, and community engagement, drawing visitors from around the world and reshaping Chicago’s South Side cultural landscape.
14. Taste of Chicago
Dates: July – August 2026 (exact city dates TBD)
Location: Grant Park | The Loop
Price: Free Entry, food and drink tickets are available for purchase
Taste of Chicago returns as the city’s premier summer food festival, now fully back in July after the NASCAR event moved to Joliet Speedway. As a local to Chicago, I think the Taste of Chicago is a great way to try foods that you most will not get to throughout the year(or ever), so it’s worth going to for that simple fact. The free festival features dozens of food vendors, trucks, and live performances from top music artists. Mark your calendar for this beloved annual tradition, perfect for foodies, families, and music lovers alike.
15. Windy City Smokeout
Dates: July 9 – July 12, 2026
Location: United Center | Near West Side
Price: TBD
Chicago’s beloved BBQ and music festival will showcase top pitmasters, craft beer, and national headliners; tickets and wristbands typically go on sale early in the year.
16. Bud Billiken Parade
Dates: August 2026
Location: Bronzeville
Price: Free Entry
Celebrate the nation’s largest African American parade at the Bud Billiken Parade. This cultural tradition features vibrant floats, performances, and a celebration of education and community, making it one of the best Chicago events in 2026 for families.
17. Northalsted Market Days
Dates: August 7, 2026 – August 9, 2026
Location: Northalsted(Boystown)/Lakeview neighborhood
Price: TBD
Northalsted Market Days® is a weekend-long, live music street festival celebrating the LGBTQ+ community in Chicago’s landmark Northalsted/Lakeview neighborhood. The 1/2 mile-long summer festival features an all-day lineup of live music on multiple stages, hundreds of vendors, food and drink, dance exhibitions, drag performances, and more.
18. Lollapalooza Chicago
Dates: Summer 2026
Location: Grant Park | The Loop
Price: TBD
Lollapalooza in Chicago is an epic 4-day music festival featuring performances from hundreds of artists from around the world across multiple stages in Grant Park. From live music to local food vendors, this iconic festival is a highlight of summer in the city.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
19. Chicago Gourmet
Dates: September 24 – 27, 2026
Location: Millennium Park | The Loop
Price: TBD
Chicago Gourmet is the premier food and drink festival in Chicago. Indulge in a weekend of fine dining, wine tastings, and chef-led demos at this annual event. This culinary celebration is one of the most exciting Chicago events for foodies and wine enthusiasts alike.
Planning a Trip to Chicago?
Check out this guide on the absolute best time to visit the Windy City.
20. Bank of America Chicago Marathon
Date: October 11, 2026
Location: Citywide
Price: Free to watch, runners’ registration required
Chicago’s iconic fall marathon returns, drawing runners and fans from around the world. Watching this global event as a spectator is so incredible. It’s inspiring to see the runners and spread positivity with others. This annual race is one of the most inspiring events of the year as marathon participants run throughout Chicago’s most vibrant and culturally diverse neighborhoods.
21. Chicago International Film Festival
Dates: October 2026
Locations: Various Theaters
Price: TBD
Chicago film lovers, save the date for the 2026 annual Chicago International Film Festival. This is the best film festival in the Midwest, featuring world premieres and award-winning films. This is one of the most exciting fall events in Chicago for 2026.
22. Open House Chicago
Dates: October 17–18, 2026
Locations: Citywide
Price: Free Entry
Explore Chicago’s architecture and design scene with Open House Chicago, a free event offering behind-the-scenes access to iconic buildings. This is one of the best free things to do in Chicago during the fall. It’s my favorite event of the season as it gives me a chance to explore new and familiar neighborhoods in a totally different way. Perfect for history and architecture lovers, this event highlights the best of Chicago’s design legacy.
23. Chicago Fashion Week
Dates: October 2026
Locations: Various Locations
Price: TBD
Chicago Fashion Week returns with runway shows and designer spotlight events across multiple venues. Celebrate style and innovation at Chicago Fashion Week.
24. Chicago Bally’s Casino
Dates: Fall 2026
Locations: Various Locations
This fall, Bally’s Chicago Casino transitions from its temporary Medinah Temple home to a permanent River West destination in fall 2026. Visitors can experience world-class gaming and a stunning new riverwalk at Bally’s Chicago Casino & Resort.
25. Chicago Thanksgiving Parade
Date: November 26, 2026
Location: State Street, Downtown Chicago
Price: Free Entry
Celebrate Thanksgiving morning in Chicago with marching bands, festive floats, and holiday cheer at this iconic parade. One of the best Chicago events to kick off the holiday season. Plus, it’s perfect for all ages!
26. Zoolights
Dates: November 2026 –January 2027
Location: Lincoln Park Zoo
Price: $0 – $10
Brighten your Chicago winter nights with this dazzling light display at Lincoln Park Zoo. Perfect for families and couples, Zoolights is one of the most beloved free events in Chicago this year.
27. Christkindlmarket
Dates: November – December 2026
Location: Daley Plaza | The Loop
Price: Free Entry
Chicago’s iconic German-style holiday market returns with festive treats, gifts, and seasonal cheer, anchoring the downtown holiday experience.
Haute Tip: Visit the Wrigleyville location for small crowds and nearby holiday pop-up bars.
Additional 2026 Chicago Celebrations & Cultural Highlights
- Illinois America 250 Celebrations: Throughout spring and summer 2026, Chicago and Illinois will mark the 250th anniversary of the Declaration of Independence with concerts, historic exhibits, performances, and themed programming across the city. Highlights include International Jazz Day (April 30) and the CSO America 250 musical series (June 2–5), culminating in July 4 celebrations. Event pricing varies by venue and activity.
- Route 66 Centennial Celebrations: Chicago kicks off the 100th anniversary of Route 66, the iconic highway that begins in the city, with celebrations throughout 2026. Events include historic vehicle rallies, guided tours, interpretive programs, and community experiences highlighting Chicago’s role as the eastern terminus. Most events are free or low-cost.
- Kick Back in Chicago — FIFA World Cup Summer Celebration: During summer 2026 (June–July), Chicago will host FIFA World Cup-themed programming across fan zones citywide. While not an official host city, the initiative features watch parties, Chicago Fire soccer events, and cultural programming to bring the tournament energy to locals and visitors. Most activities are free, with select ticketed events.
Mark Your Calendar: Top Chicago Experiences for 2026
This Chicago events 2026 guide is designed for you, fellow seeker! Balancing work, life, and play can be tricky, but staying on top of the city’s upcoming events makes it easier to plan unforgettable experiences.
Whether you’re locking in annual favorites or discovering something new, use this guide to build a year filled with moments worth showing up for. Grab your planner, start saving dates, and explore the best things to do in Chicago in 2026.
Before you go, I’d love to know: which Chicago events do you plan your year around, and which ones are new to you this year? Drop a comment, save this guide, and check back often. I’ll be updating it as new events and dates are announced, so you never miss what’s next.
Which 2026 Chicago event are you most excited about, or did I miss one you never skip? Let me know in the comments!
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