Some Like It Hot: Summer Date Ideas in Chicago
Make some ill noise for Illinois' favorite city (sorry, Springfield and every other Illinois city) because it's summer in Chicago! It may only last 90 days until the armies of winter begin to invade again, but that's why patrons of the city make them count. From baseball games to firework displays, Second City is second to none. If you're looking for some stellar date ideas this summer beyond the drab dinner-and-a-movie combo, here are our picks.

High-rise above Chi-town in a helicopter tour


Chicago may be the most perfectly planned city in America and it's time to see it properly. If eights are no big deal to you and your date, splurge on this helicopter tour to see the Chicago sights, the tiny cars and even tinier, ant-like people and pretend like riding in a helicopter is no big deal. Also, make sure to point at where you live from above with your date, like a true nerd.

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Prohibition Tour

historical tour
speakeasy crawl

Capone. O'Banion. Bugs Moran. Accardo. The biggest gangster names in the 1920s battled law enforcement in the heart of Prohibition's unofficial capital. In this tour for two, visit four still-operating speakeasies today to taste an Old Fashioned or three as you learn the history of the 18th Amendment while promptly getting boozy. You'll feel like a flapper or gangster in no time.

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Architecture tour and fireworks


We guess you could tour Chicago's best architectural sights along the Chicago River in the winter (WHY? It's called the Windy City, after all), but you may just want to cozy up on a beautiful, summer Chicago night instead. Walk (or float) through Second City's best buildings before ending with a bang-bang display of fireworks down by Navy Pier. A perfect combination of romantic and nerdy for you or your date's inner history buff.

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Deep-dish without deep pockets

Italian cuisine
chicago deep dish

Repeat after us: deep dish pizza without dipping into deep pockets. That's right, say that 5 times fast. In this romantic and fun cooking class, you'll learn the ins and outs of making a pizza pie, Chicago-style. Bring a bottle of wine or a six pack of your favorite brew to round out this warm (hopefully) Chicago night. Like a tourist, for the very first time. Remember when you first realized you loved living in Chicago? And then, how disappointed you were to realize it means that you can't do any of the dorky tourist stuff because you're a sophisticated local? Forget all that nonsense, if you can stomach standing in a crowd of tourists for an afternoon with your date. It's the perfect time to do all of the great things people love about Chicago you rarely get to experience, like Skydeck, dinner in Chinatown, horse-drawn carriages, etc. Bring on the cheese.

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Spend a day at Grant Park

We hear picnics are romantic and such, and in Chicago, picnic season is pretty short (as is summer; let's not talk about it). Spend a morning or afternoon in any part of Grant Park to appreciate the city's excellent park planning, then explore every nook and cranny of Millennium Park, the Marinas and Harbors and any number of Chicago's classiest museums.

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Classic Chicago Food Tour.


Deep-dish, Chicago hot dogs, Italian Beef, desserts and more. Skip a three-course dinner to try a little bit of everything in this walking food tour of Chicago's best restaurants, cafes and bars. Vegetarian-friendly, it's the best way to eat your way through Chicago in an afternoon.

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Catch a game at Wrigley Field

Long suffering Cubs fans make it an annual mission to venture out to Wrigley Field for America's favorite pastime/masochistic pleasure. America's second oldest baseball park's neighborhood, affectionately known as Wrigleyville, has plenty of bars, restaurants and little shops to celebrate the win afterward, or more like collectively commiserate over seeing the Cubs instead of the Sox.

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Lake Michigan

You may not be able to spend a day at the ocean, but you can spend a day on the shores of the gorgeous Lake Michigan. A haven for freshwater lovers, the beach is clean, if not a little cool from the ripping wind. Stake out a spot on any of Chicago's 26 miles of public beaches, grab some suntan lotion (and a parka and an umbrella - you never know with Chicago's weather), some chairs and soak up the sun and good weather. It doesn't happen too often.

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