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Where to Take Your Hot Chicago Date?

Couple on date

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In a city like Chicago, it can be difficult to narrow down what to do with a date, whether it be your first or your hundredth. We’ve gathered some great date ideas for you to take your partner out on the town, and our top-notch Chicago car service is here to help get you there. Check out our date ideas below and see why booking with us will make it more fun for both of you!

5 Ideas for the Perfect Date in Chitown

Among the many options open to you in the city of Chicago are:

  • Pisco Shaken cocktail

    Ice Rink

    couple rock climbing

    Scofflaw: Take your date to Scofflaw Chicago, a gin-focused cocktail and craft beer bar in Logan Square. Their Taproom Takeover nights offer an exciting variety of beers for you and your date to taste as well as an impressive spread of cocktails to choose from. And with a vintage Art-Deco facade, as well as an interior designed to emulate the look and feel of the 1920’s, Scofflaw has one of the most immersive aesthetics of any bar in the city.

  • Second City: Since 1959, Second City has been an exciting comedy and theater club. Bringing acts like Tina Fey and Steve Carrell, and a playbill that will keep you and your date entertained throughout the night! Although it’s perhaps most famous as the academy that trained Bill Murray, John Candy, and nearly every other comic to pass through SNL, the club also remains the single best place for a laugh in America’s funniest city.
  • McCormick Tribune Ice Rink: Located amid the bustle of the heart of downtown Chicago, we highly recommend renting a pair of skates and cruising hand-in-hand around this rink surrounded by some of the best views the city has to offer.
  • Maggie Daley Park Climbing Wall: Strap up and get 40 feet high with this active date destination. Beginner to expert levels are welcome to scale the walls situated in the skyline’s shadow at the edge of Millennium Park in the heart of downtown Chicago.
  • The Gage: Thrillist recommends heading down to this bar for brunch or an interesting meal and a craft cocktail, located right across from the Art Institute of Chicago, a few blocks away from the climbing wall.

Why Choose Signature Transportation?

At Signature Transportation, we offer a fleet of vehicles that are all 2012 or newer to bring you to your destination. Our vehicles are well-equipped and offer the latest technology in the automotive industry, like Wi-Fi connection and ample phone charging ports. We’ll provide the refreshments while you sit back and get to know each other a little better.

Who Does the Driving?

Our drivers have over 75 combined years of experience in the industry. Unlike other services like Uber or Lyft, our chauffeurs are tested and trained so you can be sure you’ll get to your destination safely and professionally. Our chauffeurs wear livery uniforms to match the upscale quality of our services. We offer GPS tracking so you know you’ll arrive at your destination in a timely manner.

Bring Your Chicago Date Ideas to Life with the Help of Our Car Service

Take care of reserving your date and let us get you there in style. Don’t worry about parking or traffic anywhere in Chicago—simply book a car with us today. Choose one of our luxury cars or executive SUVs to get you there. Give us a call at 844-BOOK-STG to speak with one of our office staff members, or reserve your car online with our form.