If you’re having trouble coming up with date-night ideas in the bitter cold, have no fear. Even in cold weather, Chicago provides a number of great date-night options. Warm up with your special someone with the activities featured below. (You won’t even have to give us credit for the ideas.) 

Have a favorite date spot we missed? Tell us where to find it below.


Ice skating is the ultimate outdoor activity in Chicago. Keep warm, get a workout, and find an excuse to hold hands. With many rinks to choose from in Chicago, there’s sure to be a location near you.

The Rink at Wrigley

Addison and Clark
Chicago, IL

Skate up close to the Friendly Confines of Wrigley Field. Admission on weekends is $10 per adult (Fri-Sun). Skate rentals are $10 per person on weekends (Fri-Sun) and admission and rentals are half-price during the week (Mon-Thurs).

John Hancock Observatory

Skating in the Sky
875 N Michigan Ave-94th Floor
Chicago, IL

Skate in the world’s highest ice rink! Skate indoors at the John Hancock observatory and enjoy breathtaking views of the city. Admission is $5, plus the Hancock Observatory admission fee of $9-$15. Skate rentals are $1. Book online to ensure admission.

The McCormick Tribune Ice Rink

Millennium Park
Michigan and Washington Avenue
Chicago, IL

Skate outdoors right in the heart of downtown Chicago. Take in the scenes, sip on hot chocolate, and warm up from the cold. On Valentine’s Day, take part in their themed couples skate. Admissions is free! Skate rental is available for $10.


Cooking classes are the perfect activity/dinner combination. Enjoy learning and creating together, while getting a great meal with drinks included!

The Chopping Block

Merchandise Mart Plaza, Suite 107
Chicago, IL 60654
(312) 644-6360

Lincoln Square
4747 N Lincoln
Chicago, IL 60625
(773) 472-670

Chicago’s largest recreational cooking school and gourmet retail store, offers demonstrations, hands-on cooking and wine classes, as well as private cooking parties. Classes at the two Chicago locations cover basic to advanced cooking. Also be sure to check for their date night specials.

Classes range from $45-$80.

Heat and Spice

925 West Cullom Avenue
Chicago, IL 60613
(773) 742-2331

Classes at Heat and Spice range from beginner to advanced. For a more intimate setting, classes are even offered at home or for parties of two. Depending on the class, courses may also be at the Ravenswood, Lincoln Park, and Old Town locations.

Classes range from $75-$90.


Chicago Horse & Carriage, LTD
(312) 988-9090

It may be overdone, but there’s something about a horse and carriage to make you feel like Cinderella. Chicago Horse & Carriage offers a wide variety of tours to sweep your guy or gal off their feet. Rides listed are available for 30mins – 2hrs.

Available Rides:

• Gold Coast
• Loop
• Lake
• Michigan Avenue
• Navy Pier
• State Street
• Millennium Park – 1-1/2hr ride
• Lincoln Park – 2hr ride
• Buckingham Fountain Ride – 2hr ride

Customizing rides is encouraged. Pick-up and drop off charges may apply. Special engagement packages are also offered.


Never overlook one of America’s oldest date-night gems. Chicago has a variety of bowling alleys in all neighborhoods and price-ranges.

Diversey River Bowl

2211 W. Diversey Ave
Chicago, IL

Come on down to the river and experience over two dozen sound activated lights, fog machines, strobes and music. Heart pounding Rock music will have you and your date dancing while you bowl!

Lucky Strike

River East Center
322 E. Illinois St
Chicago, IL

Lucky Strike is known for being upscale, trendy, and a great spot for lane-side drinks and food service. Enjoy cocktails and food, while you bowl!

10pin Bowling Lounge

330 N. State St
Chicago, IL

10pin redefines the bowling experience by combining a retro sport with a hip upscale lounge. Located adjacent to the House of Blues in landmark Marina City, 10pin is 20,000 square feet of high energy fun.


Chicago is home to some of the best museums in the world. See a full list of our venue guides for almost every museum in Chicago. Get inside scoops, hours, tickets, exhibit information and more.

Featured Museum Guides:

The Field Museum 101

Guide To The Museum Of Contemporary Art

Museum of Science and Industry Guide

Have a favorite date spot we missed? Tell us where to find it below. —Lauren Wulf, CBS Local Chicago