7 Chicago Winter Date Ideas

Hi! We’re a Chicago couple with a passion for telling you the best things to do in Chicago. You may know us from our Instagram page (@BestDateFood)! We know winter in Chicago can be tough at times, so we have compiled some ideas for fun dates to help brighten your winter season!

1 | Explore the Garfield Park Conservatory

Garfield Park Conservatory is one of the largest conservatories in the world, and it happens to be right here in Chicago! It is absolutely massive with so many different plant species from around the world. The conservatory is free to visit but you will need to reserve tickets online in advance while supplies last. You can reserve tickets at this link.

2 | Take a cookie decorating class

You know those oddly satisfying videos of professional cookies being perfectly decorated? Well, you can try your hand at making professional looking cookies yourself in Chicago! Bon Vivant Cakes offers workshops for both cookie and cake decorating classes. These classes sell out quickly, so plan ahead!

3 | Go on a brewery tour

A brewery tour is a great winter activity! Chicago is filled with lots of great breweries to choose from. We like the idea of pairing a visit to the Goose Island Taproom on Fulton Street with dinner in West Loop. The Goose Island Taproom offers a one-hour tour & tasting for only $15.

4 | Witness the magic of butterflies taking their first flight

The Peggy Notebaert Nature Museum offers a really cool daily experience. At 2PM each day, all the butterflies that newly emerged from their cocoons are released all at once and take their first flight. While the experience is catered towards children, it really is a beautiful sight and a calming garden to walk around (especially in the winter!). For a more adult-oriented experience, you could opt for their yoga classes located in the same peaceful Butterfly Haven!

5 | Play shuffleboard in a tropical atmosphere

Royal Palms Shuffleboard Club offers an indoor oasis that might help you forget how cold it is outside. Shuffleboard is a great activity to play with a group, so make this one a double date! Sip on cocktails while showing off your new-found shuffleboard skills and forget it is snowing outside (for a couple of hours at least!).

6 | Bowl at a retro bowling alley

You won’t find a cuter bowling alley in Chicago for a date than Avondale Bowl! This vintage bowling alley has retro vibes, manual scoring and amazing drink deals. We particularly like the half-off pitcher deals on Tuesdays. This bowling alley is 21 and older, but minors are allowed with a parent up until 7:30PM.

7 | Take advantage of Chicago’s free museum days

Every month, we post about what Chicago museums are offering free museum days. Check out our Instagram page to find the latest days you could visit the Art Institute, the Shedd Aquarium, the Museum of Science and Industry, the Planetarium and the Field Museum for free. Learn something new and enjoy being able to take a long walk indoors during the wintertime!

Hungry for more ideas? We kept this list strictly to activities. If you are looking for recommendations on where to eat, check out our list of 24 Chicago Dishes to Try in 2024!

Where do you like to go on dates in the winter? Leave us a comment!