Dating Ideas In Chicago

The windy city... seems like, on first glance, a miserable place to visit, right? Wrong! Chicago may be 'windy', but it's also an older, beautiful city that's stuffed with historical value and new, exciting attractions.

Good date ideas in Chicago aren't hard, though you might find some difficulty if you've never been in the city, or don't know where to start looking.

No worries. We've got you covered - here are our favorite date ideas in Chicago!

Wait... Wait... Don't Tell Me...!

Ever heard of NPR (National Public Radio)? Okay, so you probably have - who hasn't? Have you ever listened to their segment 'Wait Wait... Don't Tell Me!'? If you have, you probably realize that it's not only extremely funny, but pretty interesting, and makes you question what's around you.

Well, 'Wait Wait... Don't Tell Me!' is actually taped in Chicago - Chase Auditorium, to be exact - and you can sit in on a taping to test your knowledge. Figure out what's real, what's not, and who's the best, brightest, and most on top in the world of news today.

Their guest panelists rotate, and can be anything from serious journalists to comedians, or even a little of both. It's a great date, and it will leave you knowing a bit more about what's happening... and laughing.

Afterwards, take a drive KiKi's Bistro and have lunch. It's reasonably priced, which is important when you're visiting somewhere and looking to grab lunch on a budget, and the warm, inviting atmosphere adds to classic, delicious cooking and delightful service.

Couples Massage

Relaxing... invigorating... romantic... refreshing... what can you do in a city you've never been to that will be anything like those? Well, this is one of my favorite Chicago date ideas by far - it's a couples massage.

While numerous upscale spas offer this, I'm recommending SIR, which claims that it's Chicago's premier spa service for men. The reason? Not only are their prices decent when you consider what you get with their service, but the date night packages are out of this world.

Not only do you get a massage with your package, but each date night package comes with a complimentary glass of wine, and a hefty discount to a trendy and deliciously romantic dinner at Andersonville.

You can choose between numerous, but my favorites are the 'Signature', which includes a 1 hour massage, a glass of wine, and your discount, 'Hot Stone', which is a one hour hot stone massage, a glass of wine, and your discount on dinner, or the Body and Sole, which is an hour full massage, and a 45 minute foot detail, a glass of wine, and a discount on your dinner.

Oh, and what else is nice about this? Not only do they have your entire evening planned out, but they'll make your reservations at the restaurant... you don't even have to worry about it!


There's a ton to do in Chicago. If you're staying at a solid hotel, they'll be able to instruct you on other great date ideas in Chicago. Remember not to plan too seriously, though... be flexible, and leave room to explore everything and enjoy yourself.