Over 100 Captions and Quotes to Accompany Your Chicago Pictures

Instagram made easy breezy for romantic getaways and bach parties.
St. Regis - Chicago
Photo: Steve King / Getty Images
james wong - the knot contributing writer and travel expert
James Wong
james wong - the knot contributing writer and travel expert
James Wong
Travel Writer & Expert
  • James Wong is a freelance travel writer and expert.
  • He's reported for publications including VOGUE, GQ, Time Out and Thrillist.
  • James has lived in London, Tokyo and New York; and has traveled to almost every corner of the world.
Updated Oct 06, 2023

There are so many reasons couples choose to enjoy a romantic getaway or honeymoon in Chicago, Illinois. The (often captioned) Windy City is a Midwest hub for food, culture, and things to do. Best of all, it's inclusive to everybody. No wonder Chicago's been voted the best big city in America.

Lovers come for a fairytale romance fueled by four distinct seasons, whether fall gives a warm and fuzzy feeling or the magic of Christmas beckons. As for bach parties, the colossal count of restaurants, bars and nightclubs means a jam-packed weekend of festivities is always on the cards. There's absolutely no getting bored here, especially if you love sports.

Capturing moments on camera is a given these days, and sharing them with friends and family back home comes hand in hand. If you're out and about, strapped for time to think of a clever Bean caption, we're on hand to help. Here are 100-plus Chicago captions to accompany your snaps: simply copy and paste and get back to enjoying the ride. The city's sumptuous treats are calling your name.

Chicago Captions in this Article:

Funny Chicago Captions and Quotes for Instagram

Chicago, Illinois, USA downtown skyline from Lincoln Park at twilight.
Photo: Sean Pavone / Shutterstock

Well you have to have a sense of humor in snowy times, right? Proudly show off your lunchtime indulgence or embrace the city's natural elements with these cheeky one-liners.

  • The cold never bothered me anyway.
  • You're never childless when you have a husband in Chicago.
  • Head says kale salad, heart says Jibarito sandwich.
  • If you can't do deep-dish pizzas every day in Chicago, where the hell can you?
  • Windswept hair, don't care.
  • If she can wear Ugg boots, she's there.
  • I love Chicago three out of four seasons a year.
  • Chicago's where she got her Michelle Obama arms.
  • Cheese are a few of my favorite things…
  • Chicago, you blow me away.
  • Nobody comes to Chicago to get a tan.
Classic Architecture in Chicago
Photo: FeyginFoto / Getty Images

Sometimes a classic snap just needs a classic strapline. These popular Chicago captions and hashtags will sum the trip up perfectly.

  • Chicago: the middle of everywhere.
  • Greetings from Chicago, Illinois.
  • Jazz, blues, and Chicago views.
  • Wanna slice of Chicago?
  • Postcards from the Chicago skyline.
  • Breezy like Yeezy.
  • From Chicago with love.
  • The magic of big city lights.
  • #AllThatJazz
  • #WindyCity
  • #ServedChicagoStyle

Chicago Sports Captions for Instagram

Wrigley Field
Photo: Frank Romeo / Shutterstock

Chicago is big on sports, so if you're in town to cheer on the Chicago Cubs, Chicago White Sox, Chicago Sky, Chicago Bulls, or the Chicago Bears (phew), we've got just the captions for you.

  • Happiness is back-to-back ball games.
  • Nature lovers: spotting bears and cubs.
  • Like our matching White Sox?
  • Dress like a bear, act like a bear, eat like a bear.
  • In Bulls we trust.
  • It's always game day in Chicago.
  • Clubs and Cubs - we'll take both in Chi-Town.
  • Chicago Cub Squad.
  • Your cubs have landed.
  • Let's play ball.
  • Warning: Bulls and baches on the rampage.
  • I just came for the hot dogs.
  • Shoot for the stars.
  • She's cheer captain and I'm on the bleachers.

Chicago Bachelorette & Bachelor Party Captions

Chicago skyline at dusk
Photo: joe daniel price / Getty Images

Big cities mean big nights out for bachelor and bachelorette parties. Cement those unforgettable moments in Chicago with a slide show and caption. Your crew will be impressed.

  • Chicago… for one night only.
  • I don't drink anymore…but I also don't drink any less.
  • Giving them the old razzle-dazzle.
  • Cheers to Chicago!
  • On (windy) Wednesday, we wear pink.
  • Today's forecast: absolute chaos.
  • Ready to party Chi-Town.
  • Slice, slice, baby.
  • Pier pressure brought us here.
  • We don't know how to use TikTok, so here are some terrible slides and stories.
  • Da boys are back in town.
  • We're just Old Fashioned lads.
  • Bach party all-stars.
  • It's the Chicago countdown.
  • Homecoming queens coming through.
  • Brandy for the randy.

Chicago Instagram Captions for Couples

Couple kissing
Photo: Oleggg / Shutterstock

Date night or anniversary vacation, The Windy City is full of romantic corners and swoonsome restaurants to spoil the boo. Keep the folks updated back home with one of these cute captions for your Chicago snaps.

  • The crust is an important part of any relationship.
  • There's nothing more romantic than Chicago at Christmas.
  • Gone with the wind.
  • This one always floats my boat.
  • Some Midwest magic always does the trick.
  • Snuggles with blankets and bobble hats.
  • You'll find us strolling under the CTA.
  • In a pizza love triangle.
  • Romance is a date on the Magnificent Mile.
  • There's good reason why Chicago is always the setting for Christmas movies.
  • Cuddles in charming Chicago.
  • I love you, but don't even think about that last slice.
  • Baby, it's cold outside.

Chicago Instagram Captions for Honeymoons

Couple in the city
Photo: prostooleh / Getty Images

Honeymoon captions are the best way to say 'I love you' on the gram, so we've rounded up sweet ideas specifically for your romantic Chicago getaway.

  • Love you all the way up to the Willis Tower.
  • My sailor.
  • Feeling on top of the world.
  • A-maize-ing times in Illinois.
  • It ain't easy being this cheesy.
  • We go together like a sweater and boots.
  • When you snow, you snow.
  • Soaring to new heights with my love.
  • He melts my heart (and my rainbow cone).
  • You know you can make it through anything if you can brave exploring Chicago in January.
  • A happy marriage is eating your way through Chicago.
  • Pro Tip: Say 'I do' to everything Chicago has to offer you.
  • My love for you is as deep as this pizza.
  • She's the wind beneath my wings.
  • We'll never forget the Chicago chapter in our story.

Chicago Captions for Famous Attractions

Famous Cloud Gate Sculpture Chicago
Photo: Photo Spirit / Shutterstock

Make your mark on Chicago's big sights and top things to do with these clever puns and more.

  • Bean here, done that.
  • Pretty as a Chicago skyline.
  • Never ever leaving you Home Alone.
  • Concrete's cute too you know.
  • We're on cloud nine.
  • I really really really lake you.
  • Romantic riverwalks with boo.
  • Lookin' fine for 102, Chicago Theatre.
  • Hazy, lazy days in Millennial Park.
  • Chicago's bean oh-so-good to us.

Chicago Quotes From Movies & TV Shows for Captions

Home alone poster
Photo: IMDB

Whether you're painting the town Chicago red or enjoying a romantic Christmas in the snow (inspired by your childhood favorite movies), these famous quotes will jolt nostalgic memories when y'all look back.

  • 'C'mon Babe, why don't we paint the town... And all that Jazz." (Chicago)
  • "I'm in Chicago at the Drake Hotel. Call me." (My Best Friend's Wedding)
  • 'I'd like one ticket to Chicago. No baggage." (Airplane)
  • "You can like the life you're living, you can live the life you like." (Chicago)
  • "Oh Hell No! I Did Not Leave The Southside For This!" (Mean Girls)
  • "I'm an undercover reporter for the Chicago Sun Times" (Never Been Kissed)
  • "Kevin!!!" (Home Alone)
  • "In Chicago, you need your friends three times: at your wedding, your wake, and your first indictment." (The Good Wife)
  • "It's not about the food. It's about the people." (The Bear)

Chicago Quotes from Songs for Captions

In a classic pose, Frank Sinatra smokes a cigarette as he plays piano
Photo: Bettmann / Getty Images

Saying it with a song on reels? These lines are the perfect way to soundtrack your stay.

  • "You see how I played a big role in Chicago like Queen Latifah?" - Everything I Am by Kanye West
  • "Chicago is why I just grin like a clown" - My Kind of Town by Frank Sinatra
  • "Take me back to Chicago, where my music was all I had." Take Me Back to Chicago by Chicago.
  • "I think about you all the time." Dear Chicago by Ryan Adams.
  • "I'm a Chicago Southsider" - Feedback by Kanye West
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