Finding Romance in the City: A Honeymoon in Chicago

Kathy Jonas's picture
Written By
Kathy Jonas
July 16, 2015

The Windy City may be home to 2.7 million people, but it remains one of the most misunderstood, complicated and beautiful cities around. If you’re looking for a honeymoon a little closer to home, without the hassles and expense of air travel, look no further than Frank Sinatra’s “Toddlin’ Town” or Carl Sandberg’s “city of big shoulders.”


Chicago has a lakefront like no other lakefront; ethnic eateries and four-star restaurants all on the same city block; shopping ranging from the Gold Coast boutiques to vintage flea markets, top-notch theater and museums and sporting events of all kinds. The question shouldn’t be “why honeymoon in Chicago,” but “why not?” Finding romance in the city is not difficult. 



Chicago cityscapeChicago boat tour


Here are some places you shouldn’t miss (obviously some are a little “touristy” and others are a bit more “insider.”)


  • The Ferris Wheel at Navy Pier is iconic and is a replica of the 1893 World’s Fair ride. Did you know that the Chicago Shakespeare Theater is also located at Navy Pier?
  • The sky deck at the Willis Tower (formerly the Sears Tower). The deck extends for four feet outside the 103rd floor, so the ledge outside the tallest building in the Western Hemisphere is not for the feint of heart. But you will see the Chicago River and Wacker Drive in a way that the Blues Brothers never did. 
  • Savor lunch at the Terzo Piano restaurant in the Art Institute, located on the third level of the Modern Wing (you don’t need to enter the museum to dine here, but why wouldn’t you want to?) Chef Tony Mantuano, chef at the famed Spiaggia, offers a pasta dish with butternut squash, hen of the woods mushrooms and apple-thyme gremolata – yum!
  • An evening cruise on Lake Michigan. There are twice-weekly fireworks shows at Navy Pier during the summer months. The view from the water is spectacular. 


Chicago background


  • The Chicago Architecture Foundation River Cruise docents offer insider info on more than 50 buildings along the river.  Just make sure you don’t mind looking up, as you’ll be doing a lot of that. Do you know that several skyscrapers reflect the Egyptian Revival style popular after the discovery of King Tut’s tomb in 1922? 
  • The Billy Goat Tavern made famous by John Belushi  at first glance appears kind of  anti-romantic, but if you want a legendary cheeseburger,this is the place. And the bartender, Jeff Magill, who was just featured in Chicago magazine, has been there for 34 years. 
  • The Signature Room at the 95th at the top of the John Hancock Observatory. While the restaurant is not cheap, the view is incomparable. You might feel like you’ve landed on the set of one of the many romances filmed in the city,
  • The night scene simply cannot be summed up in a few words, but a few talked-about places for cocktails include The Aviari, the Violet Hour and Maude’s Liquor Bar. For those more into craft beers than concoctions, you might try the new Lagunitas Chicago Taproom, located in a brewery in Douglas Park. 
  • No list of romantic Chicago locales would be complete without mentioning a few of the historic and fabulous hotels such as the Waldorf-Astoria, The Trump International Hotel & Tower and the Ritz-Carlton. I’m partial to The Renaissance Blackstone, located on Michigan Avenue near Grant Park and all the museum campus. 


The list could go on and on, but for those who seek big-city romance, look no further than the City by the Lake.

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