If you’re in Chicago in the winter you know it gets cold. Frigid cold. But Chicago was built for the cold. And that goes for Chicago’s dating scene.
There are plenty of great winter date ideas Chicago. Here’s a list of 8 of our favorites.
1. Drinks at The Signature Room (875 N Michigan Ave, Chicago, IL)
Yes, The Signature Room can be great any time of year. But there’s a special element of charm that it provides in the winter. You can’t help but appreciate the romance of enjoying a few great cocktails on the warm 95th floor of the John Hancock Observatory while looking down on the ice cold city of Chicago. We suggest calling ahead and requesting a table next to the window. Also, have a couple of drink suggestions ready for your date. Whiskey and vodka are both great alcohols for when it’s cold out.
2. Ice Skating at Millennium Park (55 N Michigan Ave, Chicago, IL 60601)
If you can’t beat the cold, why not embrace it? Ice skating at Millennium Park is an experience you will always remember. It’s a great activity to share on a first date, or a fun memory to make if you’re in a relationship. Ice skating at Millennium Park is free. There is a fee for skate rentals and the line to rent skates can sometimes be a little long. To avoid long lines we suggest going early in the evening or renting or purchasing some used ice skates from a sports shop before you go.
3. Carriage Ride and a Movie (806 N Michigan Ave, Chicago, IL)
There’s an undeniable romance to a carriage ride in the winter. But we believe it’s even more romantic when it serves a purpose – just like it did in the old days. We suggest meeting your date at a coffee shop somewhere not too far from the theatre of your choice (we recommend AMC Loews 600 N. Michigan Ave. or AMC River East 21). Then get a couple of coffees or hot chocolates, and have the carriage pick you up and take you to the theatre. To pull this one off you’ll have to plan ahead and submit a custom ride request. But it’s worth it.
4. Dinner along the river at Smith & Wollensky (318 North State Street, Chicago, IL)
One great winter restaurant in Chicago is Smith & Wollensky. It’s a classic steakhouse that offers a sophisticated atmosphere for your date (without being so formal that you can’t enjoy yourselves). To really get the best out of the experience, we suggest calling ahead and requesting a table by the window facing the river. A great part of the appeal of Smith & Wollensky is the classy ambiance it offers while being situated right along the Chicago River. There’s an additional feeling of romance during the winter – being warm inside enjoying a great meal, while looking out onto the river and the Chicago architecture.
5. Bulls or Blackhawks Game (United Center – 1901 W Madison St, Chicago, IL)
If you know your date is a Bulls or Blackhawks fan, or they enjoy going to sporting events, this makes for a great winter date. There isn’t a bunch of energy around town during cold Chicago winters, people tend to hibernate a little. And that’s what makes Bulls and Blackhawks games great in the winter. They’re one of the only activities in the city that offers a fun, lively atmosphere. You can’t help but feel the energy when you walk into the United Center on any cold Chicago night.
6. Cocktails at the Drawing Room (937 N Rush St, Chicago, IL)
The Drawing Room is somewhat of a hidden gem right in the heart of the Gold Coast. The Drawing Room is a cozy, elegant basement dining room that specializes in cocktail mixology. And cozying up here for some great drinks on a cold winter night makes for a subtly memorable date. We recommend calling ahead and reserving a table. But if you’re looking for a last minute idea, the Drawing Room has a nice sit-up bar that offers a fun atmosphere that isn’t too loud or obtrusive for a casual, yet sophisticated, date.
7. Jazz and Drinks at The Green Mill (4802 N Broadway St, Chicago, IL 60640)
One of the iconic live music establishments in Chicago, The Green Mill, makes for an excellent winter date location. Depending on the night, The Green Mill offers Jazz, Bebop, or Contemporary music to a room that offers booth, table, and bar seating. If you’d like to get a taste of old Chicago on a cold winter night, the Green Mill is your choice – it takes pride in keeping up its historic authenticity. Because the Green Mill doesn’t take reservations, we suggest checking what time the show starts and arriving a little early – to make sure you get in, and get a decent seat. Also, one thing to keep in mind – The Green Mill doesn’t like much talking during the shows. The closer you are to the stage, the less you’ll be able to share quiet conversation with your date.
8. Aperitifs, Drinks, and Dessert at Gilt Bar (230 W Kinzie St, Chicago, IL 60654)
With its dim lighting and trendy atmosphere, Gilt Bar is a big space that offers a cozy ambiance that’s perfect on a winter date. They do some great mixology at Gilt Bar, so feel free to ask their servers about some good winter cocktails. Also, we suggest ordering some aperitifs and pairing them with your cocktails, for a fun experience. Ask your server for some suggestions. The same goes for desserts. Try pairing your dessert with the right cocktail to really maximize the taste. Depending on the night and time, Gilt Bar can get a little crowded. We recommend making reservations ahead of time.
Do you have any other great Chicago winter date ideas? If so, please leave yours in the comments below.
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