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City Cast Chicago

Emily Mack

 A journalist comes to Chicago to profile a woman attending her 500th Bears game — then falls in love with the football fanatic’s grandson.

“Holiday Touchdown: A Bears Love Story.”

 The film, which features cameos from Caleb Williams, Ben Johnson, 

, premiered earlier this month. Over the weekend, another new Chicago romance dropped: 

 in which Chloë Grace Moretz stars as an addled wedding vow writer.

While I’m not sure I’d call the Hallmark flick a rom-

), it’s fun to see our city as a romantic backdrop again. Throughout the ‘90s, Chicago was the setting for a certified banger run of rom-coms. Let’s take a trip down memory lane — or, over the river downtown, like a 

Only Sandra Bullock could not make this premise not insanely creepy: A forlorn CTA  token collector ingratiates herself into the Irish family of a handsome rider who’s unconscious in the hospital after an accident on the tracks. So Chicago. 

Look, we all agree Julia Roberts’ character is in the wrong. She spends the entire movie trying to break up two people who genuinely love each other. But I DON’T CARE. Give me the 

Less conventional than other ‘90s rom-coms, “Love Jones” is (famously) bittersweet. It also takes inspiration from 

Chicago’s underground poetry scene at that time

. Nia Long stars as a photographer who crosses paths with a writer (Darius Lovehall) at a spoken-word club.

 every chance I get — most recently on 

. The premise is ridiculous: “Grace has Bob’s dead wife’s heart!” 

 thanks to Minnie Driver’s earnest performance. It’s also Chicago angel Bonnie Hunt’s directorial debut.

These aren’t quite romantic classics but feature some unique shots of the city.

is a postmodern rom-com in which Will Ferrell’s character falls for a baker (Maggie Gyllenhaal). 

 (today La Catedral) in Little Village stood in as the bakery.

. Rachel McAdams and Channing Tatum’s characters wed guerrilla-style in the Art Institute and kiss under the Bean, McAdams flouncing in a short, rosy-pink dress.

is an extra mumbly mumblecore, starring Olivia Wilde and (Chicagoland’s own) Jake Johnson as Revolution Brewery employees. If you like “Drinking Buddies,” you might enjoy the director's Chicago-set Netflix series 

mostly takes place in Carbondale. It’s also not technically a romance, unless you count falling in love with life again. But playing a struggling writer from Lincoln Square, Gillian Jacobs checks the rom-com boxes.

More movies we love ❤️

Two new Chicago romance movies just premiered. But these are still our favorites.

Chicago Rom-Coms (and Rom-Drams)

Chicago's a Rom-Com City

Find the best of everything that Chicago has to offer.

Chicago’s Best

Chicago's Best

, is a brand-new venue for magic in Chicago, but its aim is old school. Set inside the historic McCormick Mansion, guests are invited to wander around the swanky space and experience a range of magicians close up. 

, “It marks a return to the golden age of Chicago-style live magic.”

Close-up magic, pioneered at the turn of the century by 

, is no-frills magic performed in an intimate setting. 

I grew up hearing those bar stories from my dad — specifically stories of the 

My dad, Steve, was a 20-year-old bartender there in 1975. Al was a hard-drinking, dildo-wielding magician. (He’d bang it on the bar. “The divorcees love it.”) Al also had a catchphrase: GTFM, or, “Get the f***ing money.” The acronym was emblazoned on the register. “GTFM!” he’d yell if my dad was ever distracted by 

If you were one of Al’s targets, your card might end up on his forehead. Or under your drink. You’d be looking and looking for the card while everyone else laughed.

Later, Al performed at Mycroft’s Pub on Lincoln Avenue. That was something of a magic stretch for a while, with New York Lounge and the 

The elegant Hand & The Eye mansion is a far cry from Chicago magic’s rowdy dive-bar days, but it does keep the close-up tradition alive.

 in Andersonville is also relatively upscale. However, 

entering through speakeasy laundry machines

 can make you feel like a rebel. Ticketed shows are nightly, but anyone can see close-up magic in the lobby bar.

. It’s adjacent to Goodman Theatre and Petterino's, and tickets include one drink.

 is available for bookings too. I can attest: He's spellbinding. I once saw the man do dove work in a cramped Logan Square living room!

 in Lincoln Park — not exactly a magic bar, but it’s got a fantasy vibe and, usually, a tarot card reader. Had to shout out at least one Lincoln Avenue spot!

♣️ Do you remember Heba Haba Al? I wanna know!

The Hand & The Eye is a new venue marketing Chicago-style magic. But what is Chicago-style magic?

Where You Can Still See Magic in Chicago

Chicago Was — Is? — a Magic Town

Michelle Navarro

It’s National Poetry Month, and while you can find 

 in April, poets call Chicago home all year round.

 is a poet, artist, and educator born and raised on the South Side. She is also Chicago’s poet laureate who began her two-year tenure in January.

We talked to del Valle to learn more about how her upbringing in Chicago impacts her work and what makes Chicago’s poetry scene special.

The following has been edited for length and clarity.

How does your South Side experience inspire your work?

“My earliest experiences as an artist happened in the house I'm in right now, and down the street from here. Even while I was living away from home, when I left for school, and as my career took me to NYC and LA, I always returned to many of the same themes, moments, and memories. I was gone for so long, but was always coming back, physically and metaphorically. It's just cooked into me! … I think a lot about that young woman who was running up and down 63rd St in the 90's and the things she was looking for. The way she wanted to see herself reflected in something. So I think I write for her a lot of the time.”

“I think there's a sense of community and a commitment to activism here in Chicago that you don't find in many other places. There's an underlying sense here that poetry is meant to be written and shared for a greater good, and people who do this work either know each other or know of each other, because of the level of commitment to building a better world that poetry asks of us. It's an art form that demands truth from the audience as well as the writer, and I think Chicago's scene exemplifies that in a way you don't find in many places. … It's done from a place of love for people, for the city, and from a place of "passing it on" and contributing to the lineage of poetry as a truth-telling tool. I love that.”

What is your favorite poem about Chicago, and why?

. It's just amazing to think it was written in 1914, and it remains one of the best portraits of Chicago. It's beautiful to think that what made the city so special and real back then still stands today. It's unapologetically rough, raw, never pretentious, and always defiant.”

🎤 Poetry events all month long

For more poetry events and to learn more about Chicago’s poet laureate program, check out the 

Department of Cultural Affairs and Special Events (DCASE)

It’s National Poetry Month, and while you can find a variety of workshops and open mics in April, poets call Chicago home all year round. 

3 Questions With Chicago’s Poet Laureate

What Chicago celebrities, public figures and key citizens have to say about living here.

3 Questions With Chicago Public Figures

3 Questions With

. The City of Broad Shoulders is home to the 

, which publishes “Poetry” magazine, plus constant

spoken word events and workshop opportunities. We’re on it year-round. But since April is 

 National Poetry Month, consider diving in deeper.

Some classic and more contemporary lyric odes to the complicated city we love. 

Hog Butcher for the World … City of the Big Shoulders

Chicago who wears her skyscrapers like a necklace ...

Chicago … Like loving a woman with a broken nose, you may well find lovelier lovelies, but never a lovely so real.

✒️ Favorite line: The whole thing! (It’s short.)

“the great stone lions outside monumentally pissed by jumbo wreaths and ribbons”

“whenever i’m at that land is chicago”

underneath my gym shoes. is a trail of salt. that last sentence is a test.

 “i’ll miss crossing guards ushering the grown folks too, like ducklings”

Chicago Public Library and plenty more organizations are hosting readings, workshops, lectures, and performances throughout the month.

 | April 8 | Call & Response Books | Kenwood

 | April 9 | Haymarket House | Uptown | Free

 | April 11 | Archer Heights Branch | Free

 | April 11-12 | Ruth Page Center for the Arts | Near North Side

 | April 13 | Portage Cragin Branch | Free

 | April 15 | Harold Washington Library | Loop | Free

 | April 19 | Offshore Rooftop | Navy Pier

Patricia Smith, Ashley M. Jones, Donika Kelly, Aimee Nezhukumatathil

 | April 23 | Poetry Foundation | River North | Free

Sijo and Sijo-song: Korea’s Poetry Form

 | April 25 | Little Village Branch | Free

Every month is Poetry Month in Chicago. But since April is actually National Poetry Month, consider diving in deeper. 

Celebrate Poetry in Chicago for National Poetry Month

Celebrate Poetry in Chicago

the city’s last Black-owned bowling alley

, closes permanently April 26. In operation since the 1950s, it was one of the South Side’s few remaining bowling alleys as the sport 

 after 98 years following the pandemic. More recently, 

 and closed its city site. My teenage haunt, Lincoln Lanes, burned down years ago …

There are just about a dozen bowling alleys left in Chicago. Lucky for us, though, they’re as fun as ever.

 in Logan Square — call in advance since there are lots of leagues. You can also form your own!

 in West Lawn is an old-school joint with a Sunday Special for big groups.

 may look old, but the manual-scoring spot is a fairly new addition to 

 in North Center is where it’s at. And if you’re at nearby businesses, keep on the lookout for those free coupons!

 in Jefferson Park has been a North Side birthday destination for over 50 years.

 in Forest Park is, yes, technically suburban, but it’s been a local staple since 1941.

 is located inside Marina City in River North, carrying on the 

long tradition of bowling within the famous complex

 in Auburn Gresham has 12 bowling lanes in addition to its 

 in River North and Wrigleyville. A free open house (with cheap drinks) for Wrigley’s summer league 

 in Bucktown is more known for, well, WhirlyBall, but the event space has several bowling lanes.

 in Goose Island, part of a national chain, 

Where You Can Still Bowl in Chicago

Sure, April showers bring May flowers. Tulips and cherry blossoms, specifically! But this month has a lot more than just rain in store. Check out all there is to do in Chicago.

. Just 130 galleries will be participating in the Navy Pier event, a drop of about 23%. (I will still be there, people-watching for outfit inspo.)

. That’s plenty of time to check out the jam-packed roster of shows at Landmark Century Centre Cinema in Lakeview.

showcasing filmmakers under 22 returns to FACETS in Lincoln Park 

, but April has extra opportunities to dive in:

CAConrad, Rickey Laurentiis, Jake Skeets, S Yarberry

 | April 2 | Poetry Foundation | River North | Free

 and stay tuned to City Cast Chicago all month long for more poetry events.

The eight-day Jewish celebration starts tonight! Here’s where you can 

, Easter is a time for special delicacies in Chicago. 

Then it’s time for carrot cake. Reader recs include:

And if, like me, you find lamb-shaped butter heartbreakingly nostalgic, you can pick some up at 

 in citywide park cleanups ahead of Earth Day on 

Last year, I tried to partake in 420 and had an ego death at Lottie’s after drinking a 5 mg soda. Know your limits — and consider hitting up these 

 on your journey. You can still enjoy a range of hemp products thanks to 

Mayor Brandon Johnson’s veto of the ban

April showers bring May flowers. But this month has a lot more than just rain, check out everything to do in Chicago!

Your Guide to April 2026 in Chicago

Your Guide to April 2026

, don’t forget about the city’s independent Black-owned bookstores. Here are some spots to support across the city.

One of the city’s newest bookstores, Honey & Hue opened in December. The Black woman-owned shop focuses on sharing stories about the experiences of Black people, Indigenous people, and other people of color.

Semicolon Books' physical shop is currently closed for renovations, but you can still order online. It’s set to reopen sometime this year. The nonprofit bookstore was founded by Danielle Moore in 2019 with the mission to amplify minority voices and provide a welcoming space for all readers. It's since provided thousands of free books to Chicago Public Schools students.  

, journalist trina reynolds-tyler, and organizer Andrea Faye Hart co-opened Build Coffee and Books. The shop sells books and zines about social justice and local politics — and 

Underground Bookstore is dedicated to historical literature. By offering a curated selection of books focused on Black heritage and history, they provide resources that can help educate and inspire.

Located in Hyde Park, this Black woman-owned bookstore showcases works by authors of color for readers of all ages. In addition to their curated selection, they host 

Since opening in 2007, this bookstore has developed a large collection of books for kids. It also hosts regular events. 

, Sadeqa Johnson and L. Michelle Smith both have signings and on Saturday, there’s a book brunch for kids.

Jurema Gorham owns this nonprofit bookstore, committed to bringing culturally relevant literature to Chicago’s youth. In addition to providing books to CPS, they also have a variety of events including a book club and a spelling bee.

Where do you get your books in Chicago? 📚

Here are five Black-owned bookstores you can support in the city.

Black-Owned Bookstores in Chicago

Check Out These Black-Owned Bookstores in Chicago

As the feds descend on our city, it’s hard to think of much else. But Chicago is still Chicago. And Chicago is great in the fall.

There are so many ways to soak up autumn — carving pumpkins, watching scary movies, drinking Oktoberfest ales, dressing up for Halloween … Luckily, Chicago covers it all with festivals, parades, and pumpkin patches. Whether your ideal fall day is cozy, spooky, or crafty, we’ve got a recommendation for you!

Take a hayride along the river and enjoy apple cider donuts at Island Party Hut’s autumn Saturday celebrations.

Celebrate the 40th anniversary of Scarecrow Weekend this year by voting on your favorite handmade straw watchman or making a scarecrow-to-go.

 | Oct. 19 | North Park Village Nature Center

Newsletter Editor Emmi highly recommends putting your scarecrow-making skills to the test in the scarecrow competition.

Enjoy a stroll through decorated gardens and watch the animals participate in the fall fun with themed enrichment toys!

West Chicago Fall Festival and Pumpkin Patch

Whether you want your hayride haunted or picturesque, this festival has options!

Come for Chicago’s largest corn maze, stay to enjoy the food trucks and specialty cocktails.

 | Oct. 8-12, 15-19, 22-26 | Chicago Botanic Gardens

Get inspired by hundreds of artist-carved gourds featuring tributes to Chicago sports teams, landmarks, and legends.

 | Oct. 11-12, 18-19, 25-26 | Johnson’s Farm, Hobart, IN

Pick your own pumpkins and squash — to eat or decorate with!

For the serious horror movie marathoner, check out this 24-hour film line-up!

This annual tradition has been named one of the best Halloween parades in the country, so don’t miss it!

 | Through Nov. 2 | Six Flags Great America

Embrace the screams in the scare zones and enjoy terrifying live shows after dark.

What happens when you combine fall flavors and Mexican cooking? An inspired menu featuring pumpkin ancho tostadas and apple empanadas.

Help feed your neighbors and enjoy local brews at the same time! The entry is a suggested donation to The Friendship Center.

The city’s largest Oktoberfest is back with brats, beers, and Bavarian vibes.

Whether your ideal fall day is cozy, spooky, or crafty, we’ve got a recommendation for you!

2025 Fall Fests Coming Up in Chicagoland

Fall Fests Coming Up in Chicagoland

The end of summer can feel tragic in Chicago, but don’t worry — 

temperatures shouldn’t drop consistently till the end of the month

. That means there are about 30 warm days left. Take advantage!

Stave off the end-of-summer blues with jazz. You can kick things off Sept. 1 at the 

 for $25. Later in the month, free options include:

 | Willie Dixon’s Blues Heaven Foundation | South Loop

The end of the summer can feel tragic in Chicago. That's why we're not calling it the end of summer.

arts & entertainment

Chicago's a Rom-Com City

Chicago Was — Is? — a Magic Town

3 Questions With Chicago’s Poet Laureate

Latest articles

Chicago's a Rom-Com City

Chicago Was — Is? — a Magic Town

3 Questions With Chicago’s Poet Laureate

Celebrate Poetry in Chicago

Where You Can Still Bowl in Chicago

Your Guide to April 2026

Check Out These Black-Owned Bookstores in Chicago

Latest articles

Celebrate Poetry in Chicago

Where You Can Still Bowl in Chicago

Your Guide to April 2026

Check Out These Black-Owned Bookstores in Chicago

Fall Fests Coming Up in Chicagoland

Your Guide to Chicago in September 2025

Your Guide to Chicago in February 2025