Valentine’s Day in Chicago

Made-up holiday or real declaration of love, Valentine's Day means different things to different people. If you're single in Chicago, it's either just another day or an annoying reminder of your relationship status (in which case, head to the nearest dive bar and you'll be in good company). If you're coupled up, Chicago has plenty of ways to make a February night feel less like February. Here's how to plan a date that works.

1) Book early

On an ordinary Friday or Saturday, the best restaurants in Chicago are full. On February 14, walking in without a reservation at a good restaurant is a waste of a cab fare. Many restaurants open Valentine's bookings weeks ahead, and the most sought-after tables go first, so start looking in January. If you want a preview, Chicago Restaurant Week runs from late January into early February, with set-price menus at hundreds of restaurants. It's a cheap way to scout a place before the big night.

If you're happy with something lower-key, like a casual bistro, a bar that serves real food, or two seats at the bar of a nicer place, last-minute plans are much easier.

>> Michelin-starred restaurants in Chicago

2) Be flexible about the date

Valentine's Day only lands on a Friday or Saturday every few years. You don't have to celebrate on the day itself. If you can't get the table you want on the 14th, book the night before or after, or go for a long weekend brunch instead. Mid-day mimosas count as romantic if you want them to. Many restaurants run a set Valentine's menu at a set price on the day, so an ordinary night before or after can also be cheaper. Our brunch list is a good place to start.

3) BYOB to save money

A multi-course tasting menu plus a wine pairing can easily run to a few hundred dollars for two. If you're on a budget, bring your own bottle. Chicago has a lot of BYOB restaurants, and some are proper date spots. Tango Sur at 3763 N. Southport Ave. in Lakeview, an Argentine steakhouse, is one we recommended back in 2011, and it's still BYOB, according to BYOB Chicago. Bring a Malbec for the grilled skirt steak. Confirm the policy when you book, since these things change.

The other two BYOB picks from our original list are gone. HB Home Bistro on Halsted has closed, and so has Mixteco Grill on Montrose.

>> more on BYOB in Chicago

4) Think outside the dinner box

Some of the best Valentine's plans don't involve a restaurant at all. Go see a show (Chicago Theatre Week runs through the first half of February, with cheap seats across the city; our theatre page will help you pick), spend a slow afternoon at the Art Institute, or skate the ribbon at Maggie Daley Park with the skyline around you. The Garfield Park Conservatory is the warmest date in the city, with timed tickets and a spring flower show that usually opens in mid-February. It's closed Mondays and Tuesdays.

Then have a drink somewhere with atmosphere. We used to send everyone to the Violet Hour, the unmarked Wicker Park speakeasy, but it closed for good in June 2025. Some better bets now:

• The Green Mill, 4802 N. Broadway in Uptown, is still the jazz club to go to. It has been pouring, in one form or another, since around the turn of the last century, it's cash only, and the staff will ask you to keep quiet during sets, which makes it a better date than a louder bar. Lawrence on the Red Line is a block away.
• NoMI, on the 7th floor of the Park Hyatt at 800 N. Michigan Ave., is still the classic hotel choice, with a lounge and floor-to-ceiling windows looking at the old Water Tower and the lake.
• Cindy's, on the 13th floor of the Chicago Athletic Association hotel at 12 S. Michigan Ave., looks over Millennium Park to the lake and has a glass atrium, so it works in February. Reservations open 14 days out.
• Kumiko, 630 W. Lake St. in the West Loop, is a Japanese dining bar from Julia Momosé that won Outstanding Bar at the 2025 James Beard Awards. Book through its website.

>> more on romantic things to do in Chicago
>> unique bars in Chicago
>> things to do in Chicago in February

Dress for it

Whatever you plan, it'll probably be cold. By the National Weather Service's 1991-2020 normals, February in Chicago averages a high of 35.7°F and a low of 21.8°F, and the wind off the lake makes it feel worse. A nice outfit and a real coat aren't mutually exclusive. See our Chicago weather page and what to wear in winter.

Photo by ilovememphis