Chicago date night ideas
Fresh plans around Chicago, from this weekend's highlights to events worth planning ahead for.
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Chicago Italian Beef Fest (formerly Jeff Fest) in Jefferson Park
Jeff Fest has rebranded as Chicago Italian Beef Fest! Families can still enjoy music, food, and kids' entertainment at Jefferson Memorial Park at this annual neighborhood festival.
Chicago · Jefferson Memorial ParkJefferson Memorial Park
FestivalFamilyOutdoor
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Phyllis Yvonne Stickney
Phyllis Yvonne Stickney is scheduled at City Winery - Chicago. Confirm the showtime, age rules, and entry details before you go.
Chicago · City Winery - ChicagoCity Winery - Chicago
CultureCouplesDate
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T.K. Kirkland
T.K. Kirkland is scheduled at City Winery - Chicago. Confirm the showtime, age rules, and entry details before you go.
Chicago · City Winery - ChicagoCity Winery - Chicago
CultureCouplesDate
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Christian Johnson
Christian Johnson is scheduled at City Winery - Chicago. Confirm the showtime, age rules, and entry details before you go.
Chicago · City Winery - ChicagoCity Winery - Chicago
ArtsCouplesDate
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Chris Klemens
Chris Klemens is scheduled at City Winery - Chicago. Confirm the showtime, age rules, and entry details before you go.
Chicago · City Winery - ChicagoCity Winery - Chicago
ArtsCouplesDate
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Lincoln Park Wine Fest
Get ready to raise a glass 🍷 — the Lincoln Park Wine Fest is proudly celebrating its 10th anniversary 🎉 this year in the heart of Chicago’s Jonquil Park.
Chicago · Jonquil ParkJonquil Park
OutdoorsFamilyOutdoor
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Davide De Pierro
Davide De Pierro is scheduled at City Winery - Chicago. Confirm the showtime, age rules, and entry details before you go.
Chicago · City Winery - ChicagoCity Winery - Chicago
ArtsCouplesDate
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D.L. Hughley
D.L. Hughley is scheduled at City Winery - Chicago. Confirm the showtime, age rules, and entry details before you go.
Chicago · City Winery - ChicagoCity Winery - Chicago
ArtsCouplesDate
New here? Start with Chicago
If you are new to Chicago, IL, start with the kind of day you want instead of a giant list: family-easy, adult/date, group-friendly, or weather-safe.
Family plans should be easy to enter, easy to leave, and clear about bathrooms, food, weather, and parking.
- Check age fit.
- Keep drives short.
- Pick food before the main stop.
Adult plans work best with one timed anchor and a nearby place for food or a walk.
- Check hours.
- Book if needed.
- Keep the route walkable.
Groups need one clear meet-up point and a plan that still works if people arrive late.
- Share the map.
- Pick one anchor.
- Have a backup nearby.
Weather-safe plans should stay close to the original area so the day does not fall apart.
- Check closures.
- Avoid long outdoor walks.
- Use official pages for changes.
What is coming up by place
Major venueCity Winery - ChicagoChicago · City Winery - Chicago
Local venueJefferson Memorial ParkChicago · Jefferson Memorial Park
Local venueJonquil ParkChicago · Jonquil Park
