Are you worried about the first impression you will create on your first date?
Are you on a budget and need to watch your wallet?

Check out these creative ideas for cold and warm weather that are guaranteed to get you a second date.


Wintertime Outdoor Ideas


Ice Skating in Millenium Park or the Rink at Wrigley; afterward, warm up in a coffee house.  For a truly romantic evening, make reservations to skate at the John Hancock Observatory – it’s the world’s highest ice rink!

Navy Pier Ferris Wheel – it offers a breathtaking view and is a perfect way to end a memorable evening.

How about bowling?  It seems to the be the date that time forgot.  Alleys are scattered throughout the city.  All have refreshments available and many on tap!  Get your game on by visiting Emporium Arcade Bar on N. Milwaukee Avenue in Wicker Park featuring 28 craft beers on tap.  Whether you like old school pinball or 1980’s and 90’s arcade games, show off your skills!

Spring and Summer Ideas


Take a Bike Ride – for around $10, you can rent a bike for 24 hours, plenty of time to take in some sights.

Visit a Museum – check out the Art Institute of Chicago – rumor has it that if you’re an Chicago resident, you get in free on Thursdays between the hours of 5-8:00pm.  It’s been voted #1 in the world and did you know that Barack and Michelle Obama visited on their first date?  Guaranteed success!  Also consider The Field Museum on S. Lakeshore Drive or the Museum of Contemporary Art on E. Chicago Avenue.

Take in a concert – some are free and some require tickets.   The Grant Park Music Festival runs for 10 weeks in the summer featuring classical music.  For monthly event calendars, check out

Hit the Beach!  When the weather warms up, step in the warm sand and soak up the sun.
Wine and Whiskey Tasting – check out for monthly tastings at local establishments. 

Lincoln Park Zoo – who can resist animals?  Setting this up shows your warm and fuzzy side plus the best part is that it’s free!

Food and Beverages


Bang Bang Pie Shop:  located three blocks south of the Blue Line, you can smell the coffee and deliciousness the minute you walk in the door.  Get ready for some sweet and savory pies and biscuits because who doesn’t like pie?

La Creperie:  on the border of Lakeview and Lincoln Park, enjoy a beer or wine of your choice to accompany a sweet or savory crepe.  Enjoy your treat in a rustic and old school décor or when the weather breaks, eat your goodie on the patio.  Recommended is to catch a flick at the Landmark Century Centre Cinema right across the street. 

Wormhole Coffee:  located at 1462 N. Milwaukee Avenue, this is a must for Star Wars fans.  Grab a cup of joe and check out all the movie memorabilia.  This provides the start of a great conversation!

For more info about PPM, make sure to visit!

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