Romantic Dates » Chicago, IL

Romantic Dates in Chicago, IL

Thanks to the thriving social scene, Chicago is home to countless date options. The only limit? Your imagination.
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AM Air Service Helicopter Rides

When your heart races and danger is in the air, everything, including your significant other, feels more exciting. One of the most thrilling activities to do in Chicago  is taking a helicopter ride. As the helicopter shakes and spins effortlessly in the air, you'll grab your partner's hand and see the city as you've never seen it before, returning to land with a better appreciation for your home and your love.

AM Air Service offers a variety of helicopter tours. Their downtown one will show you the United Center, US Cellular Field, Willis Tower (formerly named the Sears Tower), Millennium Park, Navy Pier, the John Hancock Building, Wrigley Field and the Chicago skyline up close and personal. The flight experience is approximately 45 minutes.  Night flights of the city lights available for a small additional surcharge.

The helicopters take off from Schaumburg airport and all major credit cards are accepted.

Avec Restaurant

Because sharing is such a selfless and loving act, tapas are a great date night dining destination. The creators of Publican and Blackbird have opened a lovely little tapas place called Avec on West Randolph Street. It can be hell getting a spot in the tiny space, but well worth it once you're sitting at the long bar or cosy tables, choosing from the many tasty tiny dishes available on the menu.

Avec features a rich old-world wine list with many unusual Spanish and Portuguese wines by the glass that you won't see in many places. The tapas are Spanish influenced but more American than anything else. You have to try the salt cod spinach artichoke dip as it is completely addictive.

If you're looking to impress your date, take him or her to this trendy, yet delicious hot spot. Romance is sure to ensue.

Broadway in Chicago

Thanks to Broadway in Chicago, there's always a number of amazing productions to choose from for a theatrical night on the town. They own a number of historic theatres including the Bank of America Theater, the Broadway Playhouse, the Cadillac Pallace, and the Ford Center for the Performing Arts and bring professional quality musicals and plays to the Chicago area. There's no need to travel to New York to see world-class musicals, the action is always here in Chicago.

Recent productions include the Lion King, Billy Elliott, and Dolly Parton's 9 to 5 musical, showing the full range of options available for a date night. Check the Broadway in Chicago website for the most up to date schedule as show durations often fluctuate, ending early or extending based on demand. It is not usually difficult to get seats and nearby good restaurants provide great pre and post theather dining options.

Chopin Theater

The Chopin Theatre is one of the hidden gems of Chicago. The space is filled with 19th century style decor and has a great artist's vibe. In addition to screening old movies and staging small production plays, they also host unique events like poetry readings and magic shows. The audience sits in couches or pulls in overstuffed dining room chairs. The performance takes place all around you. For a special romantic night, check their schedule and plan a culture filled unforgettable evening.

In addition to the stage, the Chopin Theatre also has a cozy bar and a coffee shop. Romance doesn't do well on an empty stomach. You can also head to the Exchange  nearby for a drink. Access to the theater is very convenient from the Blue Line.

Gaetano's Restaurant

Dining out in the suburbs can be a dreary experience. So many restaurants take advantage of their clientele by serving average to mediocre fare, far inferior to what you would eat in the heart of the city. Gaetano's Restaurant is the exception to the rule because Chef Gaetano has created a menu that is nothing short of thrilling. The only discomfort you'll experience is the stress of choosing between so many amazing dishes.

The pasta is all handmade, and you can taste the difference in every bite. When Gaetano offers a truffle dish, he'll personally come to the table to drown you in truffles. You won't get an overpriced, impersonal truffle ribbon there. During recent visits, the truffle and pumpkin napoleon appetizer was a standout, as well as the carpaccio.

On the nights when you can grab a table in the back room, you'll be treated to a no-menu authentic Italian dinner. The excellent food, completely different than the inventive, contemporary offerings up front, wil