City guide
Things to do in Chicago this weekend
Everything below is within about a two-hour drive of Chicago, IL — festivals, fairs, markets, museum days and one-off weekends, refreshed as new dates are confirmed. Want a wider net? The main explorer stretches the radius to four hours and lets you filter by cost and category.
This weekend near Chicago
13 listed
- Zoo Boo 2026 — Potawatomi ZooOct 16–25, 2026 — Potawatomi Zoo · South Bend, IN
- Boo at the Zoo 2026 (Milwaukee County Zoo)Oct 16–24, 2026 — Milwaukee County Zoo · Milwaukee, WI
- Sycamore Pumpkin Festival 2026Oct 21–25, 2026 — Downtown Sycamore / courthouse lawn · Sycamore, IL
- Milwaukee Astronomical Society Open House: Spooky Skies 2026Oct 23, 2026 — Milwaukee Astronomical Society Observatory · New Berlin, WI
- Arts in the Dark Halloween Parade 2026Oct 24, 2026 — Columbus Drive, north from Balbo to Jackson · Chicago, IL
- All Aboard the Spooktacular Express 2026Oct 24, 2026 — National New York Central Railroad Museum · Elkhart, IN
- Music Box of Horrors 2026Oct 24–25, 2026 — Music Box Theatre · Chicago, IL
- South Bend Fall Artisan Market 2026Oct 24–25, 2026 — Century Center · South Bend, IN
- Pontiac Family Fall Fest 2026Oct 24, 2026 — Chautauqua Park · Pontiac, IL
- Family Spooktacular 2026Oct 24–25, 2026 — Naper Settlement · Naperville, IL
- Chicago Women's Expo + Great Food Expo 2026Oct 24–25, 2026 — Donald E. Stephens Convention Center — Hall F · Rosemont, IL
- Brookfield Toy Vault October Funko Show 2026Oct 24, 2026 — Brookfield Square Mall · Brookfield, WI
- Chicago Toy Show — October 2026Oct 25, 2026 — Kane County Fairgrounds · St. Charles, IL
Coming up near Chicago
Page 3 of 3 — 119 listed
- International Gem & Jewelry Show — Rosemont December 2026Dec 11–13, 2026 — Donald E. Stephens Convention Center — Hall G · Rosemont, IL
- 14th Annual Krampus Fest at Martyrs' 2026Dec 12, 2026 — Martyrs' · Chicago, IL
- Shipshewana on the Road — Valparaiso Fall 2026Dec 12–13, 2026 — Porter County Expo & Fairgrounds · Valparaiso, IN
- Renegade Craft Chicago — Winter 2026Dec 18–20, 2026 — Bridgeport Art Center · Chicago, IL
- Brookfield Toy Vault Christmas Show 2026Dec 19–20, 2026 — Brookfield Square Mall · Brookfield, WI
- Waukesha Pokémon/TCG Non-Sports Card Show – December 2026Dec 20, 2026 — Waukesha Expo Center – Forum · Waukesha, WI
- Illinois Home Show — Rosemont January 2027Jan 9–10, 2027 — Donald E. Stephens Convention Center — Hall A · Rosemont, IL
- Illinois Bridal & Wedding Expo — Rosemont January 2027Jan 9–10, 2027 — Donald E. Stephens Convention Center — Hall A · Rosemont, IL
- Capricon 2027Jan 28–31, 2027 — Marriott Chicago O Hare · Chicago, IL
- Greenberg’s Great Train & Toy Show – Grayslake 2027Jan 30–31, 2027 — Lake County Fairgrounds & Event Center · Grayslake, IL
- Lake Geneva Winterfest 2027Feb 3–7, 2027 — Riviera Plaza and Flat Iron Park · Lake Geneva, WI
- Chicago Auto Show 2027Feb 13–21, 2027 — McCormick Place · Chicago, IL
- Anime Milwaukee 2027Mar 5–7, 2027 — Baird Center and Hilton Milwaukee · Milwaukee, WI
- Chicago World of Wheels 2027Mar 12–14, 2027 — Donald E. Stephens Convention Center · Rosemont, IL
- Obscura Paracon 2027Mar 20–21, 2027 — Altgeld Hall, Northern Illinois University · DeKalb, IL
- Hall of Heroes Comic Con 2027Apr 3–4, 2027 — Century Center · South Bend, IN
- AdeptiCon 2027Apr 7–11, 2027 — Baird Center · Milwaukee, WI
- Chicago Spring Showcase of Miniatures 2027Apr 8–10, 2027 — Chicago Marriott Schaumburg · Schaumburg, IL
- Milwaukee Lionel Railroad Club Open House – Spring 2027Apr 10–11, 2027 — Milwaukee Lionel Railroad Club – Parkland Plaza · New Berlin, WI
- Milwaukee Auto Show 2027Apr 15–18, 2027 — Wisconsin State Fair Park Exposition Center · West Allis, WI
- Midwest Gaming Classic 2027Apr 23–25, 2027 — Baird Center · Milwaukee, WI
- Chicago Toy Show — April 2027Apr 25, 2027 — Kane County Fairgrounds · St. Charles, IL
- One of a Kind Spring Show Chicago 2027Apr 30 – May 2, 2027 — THE MART · Chicago, IL
- C2E2 2027Apr 30 – May 2, 2027 — McCormick Place — South Building · Chicago, IL
- Anime Central 2027May 14–16, 2027 — Donald E. Stephens Convention Center and Hyatt Regency O Hare · Rosemont, IL
- Milwaukee Horror Con 2027May 14–16, 2027 — Baird Center, South Building · Milwaukee, WI
- Cavalcade of Planes 2027Jun 5–6, 2027 — Clow International Airport · Bolingbrook, IL
- Illinois St. Andrew Society Scottish Festival and Highland Games 2027Jun 11–12, 2027 — Caledonia Senior Living and Memory Care · North Riverside, IL
- PUDDLE 2027 – Life Is a CircusJun 12, 2027 — Holiday Inn Chicago O’Hare – Rosemont · Rosemont, IL
- Anime Midwest 2027Jul 2–4, 2027 — Donald E. Stephens Convention Center · Rosemont, IL
- Gerber Collision & Glass Route 66 NHRA Nationals 2027Jul 9–11, 2027 — Route 66 Raceway · Joliet, IL
- Chicago Toy Show — July 2027Jul 25, 2027 — Kane County Fairgrounds · St. Charles, IL
- Wisconsin State Fair 2027Aug 5–15, 2027 — Wisconsin State Fair Park · West Allis, WI
- Milwaukee Irish Fest 2027Aug 19–22, 2027 — Henry Maier Festival Park · Milwaukee, WI
- Fan Expo Chicago 2027Aug 20–22, 2027 — Donald E. Stephens Convention Center · Rosemont, IL
- NIU STEMfest 2027Sep 18, 2027 — Northern Illinois University campus · DeKalb, IL
- Milwaukee Lionel Railroad Club Toy Train Sale – 2027–2028Oct 17, 2027 – Mar 19, 2028 — New Berlin Entertainment Center · New Berlin, WI
- Chicago Toy Show — October 2027Oct 24, 2027 — Kane County Fairgrounds · St. Charles, IL
- Milwaukee Lionel Railroad Club Toy Train Sale – Fall 2028Oct 22 – Dec 17, 2028 — New Berlin Entertainment Center · New Berlin, WI