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From improv shows and ice cream crawls, to Segway tours and staycations, here are the best ways to woo a significant other in the Second City now.

Chicago has no shortage of skyline views, but the one from Cindy’s at the Chicago Athletic Association -- complete with vistas of Millennium Park, Lake Michigan, and the Jay Pritzker Pavilion -- has date night written all over it.

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Once you’ve worked up an appetite, head just up the river for lunch or dinner at the Moshulu, where you can enjoy breathtaking views, delicious fare and crave-worthy cocktails aboard this fully restored, four-masted sailing ship.From there, venture back to your nearby hotel room at the Hilton Philadelphia at Penn’s Landing.With those in mind and some of the great ideas I’ve seen or gathered via Pinterest- BAM I was at 90!I felt selfish not sharing this on the blog, I mean after all I already typed this!Outdoor concerts are low-pressure, laid-back, and the perfect opportunity to talk as much -- or as little -- as you want.

Headliners this summer include Drive-By Truckers, Hurray for the Riff Raff, and Lady Wray.

I started with this spreadsheet and then added some others we had already done or I had heard of others doing. I decided to add some more free dates since many use a budget or lack of as one of the excuses to not date, and I wanted to help with that issue!

I also wanted to come up with some at-home dates for those with small children that are hard to leave.

Do some research before you leave so you know which constellations to look for.13. Swing on the swings, play Frisbee, or feed the ducks.14. Local museums usually don’t cost much to get in.15. Each person gets (or whatever amount you decide) to spend on any food item at the grocery store for dinner.

If the weather doesn’t permit an outdoor picnic, lay out a blanket on the floor and eat in the living room.11. Whether it’s at your local community theater, high school, or a big-city play house, there is plenty of entertainment available in most areas.12. Pack a blanket, pillows, and food (like our Ham and Swiss Poppy Seed Sandwiches), and go somewhere to see the stars.

Be sure to have some treats for the occasion, like our Gooey Almond and Coconut Chex Mix.6. Find out what tourist attractions are in your city and spend the night acting like tourists—don’t forget to take lots of cheesy pictures!