What to Do in Chicago by Day or Night

Day

Daytime Things To Do see more daytime things to do in Chicago

Night

Nighttime Things To Do see more nighttime things to do in Chicago

The Windy City is a metropolis that is deeply affected by the weather, but regardless of the season, there are plenty of things to do in Chicago year round.

The nightlife scene is mostly indoors in the winter and the city itself is also a subdued beast locked in a deep freeze during the day. This is not to imply that everyone goes into hibernation (certainly not the shirtless Bears fans at Soldier Field) but crowds at most outdoor locales are comparatively scant.

As soon as the April / May thaw arrives, however, residents shake off their cabin fever and make any excuse to soak up the sun. Runners, bikers, and all-around outdoor lovers blanket the city’s nineteen miles of uninterrupted lakefront paths, and popular Lake Michigan beaches like ritzy Oak Street and rowdy North Avenue become a sea of skimpy swimwear and volleyball tournaments.

The city’s network of more than 550 parks – including Grant / Millennium, Lincoln, and Northerly Island – swell with things to do like softball games, sunbathers, dog walkers, and barbecue gods on any warm day. The carnival rides, events, and major promenade at Navy Pier are an obvious choice for first-time visitors, though the area’s cornucopia of cafés and theaters appeals to long-time residents as well.

Even before the thermometer inches past fifty, people head out in the morning to popular brunch spots and fantastic shopping districts to snatch up everything from haute couture along the landmark Magnificent Mile to quirky and trendy wares in Wicker Park.

And even though there are no traditional happy hours in Chicago, no summer would be complete without a day at one of its ballparks, whether in Bridgeport’s Sox country or sitting in the sun behind the ivy walls at historic Wrigley.

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What are you in the mood for?

  1. Lucas

    Sports? Pub crawls? Rowdy bars? Good beer? Then check out these suggestions from Lucas:

    Lucas Likes: Beer Sports Rowdy Casual Anything goes Bar Flirty

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  2. Adriana

    Exclusive hotspots? Chic crowds? Bottle service? Posh shopping? Then check out these suggestions from Adriana:

    Adriana Likes: Exclusive Nightclub Fashion Forward Shopping Jetsetter Lounge Hotel Bar High End / Exclusive

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  3. Jonah

    Eclectic crowds? Authentic bars? Live music? Nothing mainstream? Then check out these suggestions from Jonah:

    Jonah Likes: Live Music Eclectic Indie Alternative Non-mainstream Laid back Conversational Creative / Art / Music Types

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  4. Emma

    Amazing drink deals? Unpretentious crowds? Karaoke with friends? Dancing all night? Then check out these suggestions from Emma:

    Emma Likes: Happy Hour Culture Dancing Lively Budget-friendly Sightseeing Party Groups

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... or find things to do by interest

  • Sports
  • Live Music
  • High Energy
  • Laid back
  • Beer
  • Students
  • Shopping
  • Exclusive
  • Conversational
  • Sightseeing
  • Budget-friendly
  • Free
  • Dog Friendly
  • Expensive
  • Dancing
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