If you’re like me, planning is non-negotiable, especially if you’re packing your calendar with exciting events in Chicago.
Whether you are hosting friends, chasing your favorite summertime vibes, or simply staying ahead of Chicago’s lively event scene, this guide covers you.
There is so much happening year-round that it can be easy to let time slip away and miss out on your favorite annual events.
Let The Haute Seeker’s guide to exciting Chicago Events be your ultimate resource so you can make the most of what the city offers, stress-free.
Chicago Events and Experiences 2025
1. Chicago Restaurant Week
Dates: January 24–February 4, 2025
Locations: Citywide
Price: $30 – $60
Sample the best food in Chicago during Chicago Restaurant Week. This year, the specialty food event will feature more than 470 eateries, spanning 35 neighborhoods, with 71 resultants participating for the first time. For 17 consecutive days, diners enjoy special prix fixe menus, priced at $30 for brunch or lunch, or $45/$60 during dinnertime. This is one of the best and most affordable things to do in Chicago this January.
2. Chicago Theatre Week
Dates: February 6 -16, 2025
Locations: Citywide
Price: $15 – $30
Experience live theater in 2025 at a discounted rate during Chicago Theater Week. For arts and culture lovers— this is one of the best events that you can experience in Chicago this year. During Chicago Theatre Week guests can enjoy more than 100 performances at theaters across the city with ticket prices ranging between $15 – $30 dollars. 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 10–18, 2025
Location: McCormick Place | South Loop
Price: $0 – $17
The Chicago Auto Show, one of the most exciting Chicago events of 2025, returns to McCormick Place. This is one of the largest auto shows in North America that showcases the latest vehicles including cross-overs, pick-ups, concepts, and more from 20+ manufacturers from around the world. This annual event showcases everything from electric cars to luxury vehicles and interactive exhibits. A must-see for car enthusiasts and families, it’s a great way to kick off the year and get out of the house during the chilly month of February.
4. St. Patrick’s Day Parade
Date: March 15, 2025
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. C2E2 (Chicago Comic & Entertainment Expo)
Dates: April 11–13, 2025
Location: McCormick Place | South Loop
Price: $50 – $350
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 memorable experiences. From comics to gaming, this is one of the top things to do in Chicago this spring.
6. EXPO Chicago
Dates: April 24–27, 2025
Location: Navy Pier | Streeterville
Price: $36 – $165
EXPO Chicago is the biggest contemporary art event in Chicago. This internationally acclaimed art fair features galleries, installations, and artist talks, at Navy Pier, along with city-wide activations that highlight the local community. This cultural highlight is perfect for art lovers seeking unique things to do in 2025.
Haute Tip: Many events offer early-bird tickets and season passes. Set calendar reminders a few months ahead for the best deals.
7. Chicago Farmers Markets
Dates: May 17 – October 30, 2025
Locations: Citywide
Price: Free Entry
Shop for farm fresh goods and produce at one of Chicago’s city farmers’ markets. This is one of those things to do in Chicago when you’re feeling adventurous and wanting to explore. Farmers’ markets occur daily throughout various Chicago neighborhoods and are free to attend. Eat fresh and local when you shop the Chicago Farmers Market this summer.
8. Chicago Baseball: Crosstown Classic
Dates: May 16-18 & July 25-27, 2025
Locations: Wrigley Field & Guaranteed Rate Field
Price: $50 – $10,000
Cheer on Chicago’s biggest baseball rivalry as the Cubs face off against the White Sox in the Crosstown Classic. This exciting Chicago event brings fans from across the city together for a fun tradition of sports and hometown pride.
9. Summer Saturday Fireworks at Navy Pier
Dates: May 24 – August 30, 2025
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. NASCAR Chicago Street Race
Dates: July 5–6, 2025
Location: Grant Park | The Loop
Price: Starting at $99
Start your engines for the NASCAR Chicago Street Race. This thrilling event brings high-speed action to the heart of the city, making it one of the most exciting things to do in Chicago this summer. Watch professional drivers navigate the streets of downtown in this electrifying experience.
11. Windy City Smokeout
Dates:July 10–13, 2025
Location: United Center | Near West Side
Price: $59.95 – $269.95
This summer, enjoy a weekend filled with BBQ, craft beer, and country music at the Windy City Smokeout. One of the best Chicago events of the season, it’s a foodie’s paradise and a must-attend outdoor festival for country music lovers.
12. Lollapalooza
Dates: July 31 – August 3, 2025
Location: Grant Park | The Loop
Price: $189 – $25,000
Returning in 2025 is one of the best festivals in Chicago, Lollapalooza. This epic 4-day music festival features performances from 170+ artists from around the world across 8 stages. From live music to local food vendors, this iconic festival is a highlight of summer in the city.
13. Bud Billiken Parade
Dates: August 9, 2025
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 this year for families.
14. Northalsted Market Days
Dates: August 9–10, 2025
Location: Northalsted(Boystown)/Lakeview neighborhood
Price: Free Entry, $20 suggested donation
Celebrate community and experience live music this summer during Northalsted Market Days®. This is a weekend-long, live music street festival celebrating community in Chicago’s landmark Northalsted/Lakeview neighborhood. The 1/2 mile-long summer festival features an all-day lineup of live music on 5 stages, 250+ vendors, food and drink, dance exhibitions, drag performances, and more.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
15. Taste of Chicago
Dates: September 2025
Location: Grant Park | The Loop
Price: Free Entry, food and drink tickets are available for purchase
This summer, the city’s most well-known food festival returns to Grant Park in downtown Chicago. The beloved food festival tradition spotlights Chicago’s incredible and diverse food scene. The free event features dozens of vendors, food trucks, and performances from some of music’s most well-known artists. Mark your calendar for this annual tradition, perfect for foodies, families, and music lovers. Can’t make it to the main event? Check out neighborhood pop-ups for a mini experience of the Taste, featuring local artists and neighborhood restaurants.
16. Chicago Gourmet
Dates: September 25–28, 2025
Location: Millennium Park | The Loop
Price: TBD
Indulge in a weekend of fine dining, wine tastings, and chef-led demos at Chicago Gourmet. This annual 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.
17. Chicago Fashion Week
Dates: October 1–7, 2025
Locations: Various Locations
Price: TBD
Celebrate style and innovation at Chicago Fashion Week. This annual showcase of emerging designers and established brands is one of the top Chicago events for fashion enthusiasts this year.
18. Bank of Chicago Marathon
Date: October 12, 2025
Location: Citywide
Price: Free to watch, runners registration required
Join thousands of spectators to cheer on runners at the iconic Chicago Marathon. 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.
19. Chicago International Film Festival
Dates: October 2025
Locations: Various Theaters
Price: TBD
Film lovers, don’t miss out on one of the best film festivals in the Midwest, the Chicago International Film Festival. Featuring world premieres and award-winning films, this is one of the most exciting fall events in Chicago for 2025.
20. Open House Chicago
Dates: October 18–19, 2025
Locations: Citywide
Price: Free Entry
Explore Chicago’s architectural wonders with Open House Chicago, a free event offering behind-the-scenes access to iconic buildings. Perfect for history and architecture lovers, this event highlights the best of Chicago’s design legacy.
21. Chicago Thanksgiving Parade
Date: November 27, 2025
Location: State Street, Downtown Chicago
Price: Free Entry
Celebrate Thanksgiving morning 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!
22. Zoolights
Dates: November 2025 –January 2026
Location: Lincoln Park Zoo
Price: $0 – $10
Brighten your 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.
23. Christkindlmarket
Dates: November 21–December 24, 2025
Location: Daley Plaza | The Loop
Price: Free Entry
Step into a European-inspired holiday market with unique gifts, festive treats, and cheerful vibes. Christkindlmarket is one of Chicago’s most magical free events during the holiday season. If the downtown holiday crowd is too much for you, make your way out to Aurora for the market location in the suburbs.
Stay Ahead with this Chicago Events Guide
This Chicago events guide for 2025 is all for you, fellow seeker! Juggling work, life, and play, can be challenging, but staying informed about upcoming events in the city can make all the difference.
So grab your planner and start marking dates for these exciting Chicago events. Cheers to a year filled with amazing experiences!
