Great Dates in 50 States: Chicago, IL

Great Dates in 50 States: Chicago, IL

by Jake Albright,

 The Windy City can be a tough spot to visit in the winter months, but in the summer the city is open to exploration and adventure. America’s third largest metropolis has a diverse selection of possible dates and here are just a few of the most popular.

Cubs Game at Wrigley Field

You shouldn’t think of attending a Cubs game as a sports outing, you should think of it as a cultural exploration. Not only are the Chicago Cubs fans famously sullen, having endured a World Series dry spell that extends to 1908, but they are a well-intoxicated bunch as well! The beers at Wrigley are served like they are in stadiums around the country, but the attitude in the stands is jovial and outgoing. Maybe its all the frigid months Chicagoans spend hiding in heated building, or the architecture of the stadium which takes you back to the early 20th century, but the fans here are ready to party.

Be sure to line up good tickets well in advance, and for a unique opportunity check out the rooftops at the nearby buildings!

Cubs Homepage:

1060 West Addison Street,

Chicago, IL 60613

(773) 404-2827

Rooftop Tickets:

Shedd Aquarium

If you like fish then you MUST check out one of the world’s largest and most complete aquatic life exhibits. The Shedd has been one of the go-to date spots in Chicago for decades. The Waters of the World exhibits take you around the world via waterways and unique water creatures. Be sure to check and see which exhibits are being shown. Right now the Shedd is featuring Jellies, one of the most popular exhibits in the museum’s history.

John G. Shedd Aquarium
1200 S. Lake Shore Drive
Chicago, IL 60605

Walk Along the Lakeshore

Chicago sits on Lake Michigan and in the summers the lake is alive with activity. Passing boats and jet skis make even a random Wednesday afternoon entertaining for those looking out onto the water. The lake is the center of Chicago’s activity in the summer and for those who visit in August there is even a chance to see the Air & Water show, one of the summer’s biggest hits.


Drinks at the John Hancock Building

Everyone talks about the Sears Tower (now called the Willis Tower) but it’s actually that building’s architectural cousin, the John Hancock Building that offers the most for those on a date. The Signature Room is one of the most popular date spots in the city, allowing guests at the bar on the 95th floor a view of the entire city. At night there is almost nothing that can compare to the view.

875 N. Michigan Avenue

Chicago, IL 60611

These are the very best offerings in a city that is filled with things to do and places to see. Like all great metropolises the City of Chicago is a place where you can get swept into romantic dinners by the river or walking dates along the Magnificent Mile. Be sure to explore and you can’t go wrong!

Jake Albright 

After spending his post-collegiate years living like a bachelor in NYC, Jake spent his late twenties in LA in a loving and committed relationship. Now bi-coastal, and once-again single, Jake has used his experiences to become the lead writer for A former college athlete, he now spends his extra time traveling to visit friends and take new adventures.

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