See an Outdoor Movie or Music Performance
The Chicago Park District is still hosting movies through the end of the week, aka this week -- the LAST week of August. Millennium Park is still hosting live performances through September, including live Jazz shows this Friday. Go to explorechicago.org to learn more!
Buy Something from The Market
They have these everywhere. I searched the list on Explore Chicago for you and came up with 227 results. There's nothing more summery than fresh flowers from the market and sharing a glass of wine over some cheese and fruit you bought that morning. So get out of bed early and check out one of the many great markets in this city! Heck you can even go on your lunch hour if you work near Daley Plaza.
Go to a FestivalI don't care if doesn't sound your style. I'm not concerned that the only one happening is far from your neighborhood. Nothing defines a Chicago summer better than festivals. So find one and GO! Metromix always has a great list of events.
Barbecue, picnic, terrace, rooftop, breakfast, lunch hour or dinner. Eat outside as much as possible before you can't anymore. There are tons of great rooftops and outdoor dining options in Chicago. Check out this list from OpenTable.com
Have a Picnic
Get a few friends, some blankets and food and go to the nearest park you can find. Go on a Sunday afternoon or one evening after work. Beautiful summer weather shouldn't be missed!
Go for Walks
I tend to be an inside girl. Then I go outside and I yell at myself for waiting for a necessity to drag me out. Before summer's over just walk around the block, go for a bike ride. Don't be like me. Get outside after work and enjoy the weather. You don't need plans or an activity and don't make excuses for all the stuff you have to do that happens to be inside. Just go out.
Go to the Beach
Every year this one misses me. It's the obvious summer activity yet somehow I find myself lucky if I make it once. So before it gets cold get yourself in a bathing suit and acquire a tan line. Even if it only lasts for a day.
Do Something Touristy
Bike tour, boat tour, cruise tour, chocolate tour, history tour. Whatever it is, be a tourist in your own town and do something you normally make fun of matching-sweatshirt-wearing, walking-six-people-wide foreigners/suburbanites (ehem, tourists) do. Go to Navy Pier and get ice cream. Wander around Millennium Park. Take the gangster tour. Go to a zoo and pretend like you've never see animals before. Then get ice cream.
Go To a Sports Game
Pick one. I hear there's a bunch.
Have a Chill House Party
Don't all the hit tv shows have people wearing fabulous yet simple outfits, drinking martinis their bffs make perfectly and just hanging out at the rich kid's really cool house? Because that's what you do in the summer. You don't need to be on tv or even fabulously dress, but you do need to make time to just relax a little, enjoy some r&r with friends and pretend as though you're 15 again with no responsibilities. So pick a house, pick a drink, play some music and call it a party.