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Your Guide to Chicago in February 2025

Posted on January 30, 2025   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Chicago skyline at sunset

Chicago might just be one of the most romantic cities in the world 😍 (Pixabay / StockVault)

City Cast

Your Guide to February 2025 in Chicago

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Between Valentine’s Day and other holidays, there’s lots to love about Chicago in February. Here’s how we’re making the most of the month.

Valentine’s Day Fun

Making dinner reservations around Feb. 14 can be competitive. Plan a unique date instead to a board game cafe like Stay and Play in Irving Park or a vinyl store like Out of the Past Records in Garfield Park.

Galentine’s brunches and crafts are fun and all, but take inspiration from these locals who turn their home into a cafe 😍 Or swap coffee for cocktails and create a basement bar like your favorite Chicago auntie.

Or just treat yourself. (Once again, City Casters stan AIRE Ancient Baths.)

More Celebrations

Ring in Year of the Snake

Lunar New Year celebrations are underway between performances, dumpling workshops, and mahjong nights. But we’re perhaps most excited about parades on Argyle and in Chinatown next weekend.

Honor Black History Month

The monthlong commemoration has roots on the South Side. Now, Chicagoans can seek out the new Pan-African art exhibit at the Art Institute, attend the Uniting Voices’ Afrofuturism concert, and support Black businesses during Chicago Black Restaurant Week.

Bill Murray in “Groundhog Day”

Bill Murray in “Groundhog Day,” which was shot in Illinois. (Columbia Pictures / Getty)

Will Groundhog See Shadow?

If you love the 1993 Bill Murray movie filmed in Woodstock, Illinois, head to the northwestern town for Groundhog Days this weekend. Events include a musical adaptation of the film, walking tours, groundhog trivia, and a themed 5K. Navy Pier is also hosting its second annual celebration Sunday.

Where to Seek Out Entertainment

Chicago Theatre Week Deals

A production of “A Raisin in the Sun?” A play about the Bronzeville parlor game that inspired the lottery? Choose from more than 100 performances for as low as $15 during the city’s promotion Feb. 6–16.

Super Bowl Watch Parties

Watch the Super Bowl with other bitter Bears fans at the Verizon FanFest at Soldier Field on Feb. 9. Rooting for the Birds? Head to The Reveler in Roscoe Village. Part of Chiefs Kingdom? Watch the game from Toons Bar & Grill in Wrigleyville. Now is the time to get your ticket for Kendrick Lamar and SZA’s Chicago concert before prices increase after the halftime show.

The Chicago Botanic Gardens’ orchid show in 2024

The Chicago Botanic Gardens’ orchid show in 2024. (Sidney Madden / City Cast Chicago)

Take in ALL the Flower Shows

Craving spring? So is everyone else in Chicago. Book your reservations ASAP for the Chicago Botanic Garden’s orchid show opening Feb. 8 and the Garfield and Lincoln Park conservatories’ flower shows opening Feb. 12. The team shared tips last spring for how best to enjoy the shows.

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