As the third largest city in the country, Chicago, Illinois, is never short on entertainment, activities and things to do. From the breathtaking lakefront to the sophisticated shops and eateries along the Magnificent Mile, Chicago has a lot to offer both residents and visitors. For couples looking for fun, adventure and creative dates, Chicago's got you covered, no matter what the weather or time of day.
For a sophisticated but fun date night, check out 10pin in downtown Chicago. This hip and stylish bowling lounge offers more than your average bowling alley. At 10pin, you and your sweetie can sip on high-end cocktails and indulge in gourmet sliders while seeing who's the best bowler. It also features lounge areas where you can just kick back and enjoy the music. The Navy Pier is a classic spot for couples that never gets old. Enjoy an evening at Pier Park at the very end of the pier, which features classic carnival-style rides. You and your love could ride the Ferris Wheel, the wave swinger, or check out the funhouse maze. You could also rent bikes from the pier and follow the path along the shores of Lake Michigan for a scenic ride.
Laugh It Up
If you and your significant other love to laugh, you have to check out one of Chicago's famous comedy clubs to see both local and national comedians give side-splitting performances. The Laugh Factory on the northside is one of the most well-known and is almost always a guarantee for a night of good laughs. If sketch comedy is more your thing, you must take your sweetie to the Old Town neighborhood to see a show at Second City, world famous for the celebrity comedians that got their start there. A new, innovative and hilarious show is always on, so you'll never have the same experience twice. Some of the shows require audience participation, giving you the opportunity to impress your date with your comedic chops.
Creative Couples Classes
Chicago is chock full of enrichment classes, from cooking to art, and many offer classes especially geared toward couples. If the two of you enjoy food and cooking, take a class at the Chopping Block in downtown, a culinary store that offers a wide variety of cooking classes for children and adults. The Chopping Block also offers classes for couples a few times a month, such as their Date Night classes where you and your honey will learn how to make classy, date-worthy meals. If you are more artistically inclined, head to Bottle and Bottega in the Lincoln Park neighborhood, a one-of-a-kind art and wine party studio. As a couple, you can join a public art party where trained instructors lead you in completing a painting while enjoying your favorite wine and beer.
Chicago's Seasonal Entertainment
Chicago is one city that is never short on live entertainment and events, no matter what time of year. In the summer, the Taste of Chicago is the premiere summer festival and if the two of you love food, it is the place to be. Sample classic Chicago favorites like deep dish pizza and Italian beef, as well as high-end options from celebrity chefs on the Chicago foodie scene. The Taste of Chicago always has a stellar lineup of live music performances that are completely free as well. Chicago SummerDance is another free experience where you and your sweetie will learn how to samba, salsa, meringue and line dance with professionals and hundreds of other couples in Grant Park. In the winter, head to Millennium Park to skate hand-in-hand at the McCormick Tribune Ice Rink. Enjoy views of the city skyline while skating, then tuck into the Park Grill restaurant next to the rink for gourmet hot chocolate.
- 10 Pin: Bowl
- Navy Pier: Things to Do -- Pier Park
- Laugh Factory: Chicago's Best Standup
- Second City: Home
- The Chopping Block: Cooking Class Info
- Bottle & Bottega: Public Parties
- Choose Chicago: Taste of Chicago
- City of Chicago: Chicago SummerDance
- Choose Chicago: McCormick Tribune Ice Skating Rink