Allison Yates

Chicago is an undoubtedly a city of romance. Across the Windy City, our charming tree-lined parks, sultry speakeasies, and staycation-worthy historic hotels seem to exist solely for lovers in search of things to do together. From taking in sunset views atop some of the world's tallest buildings to intimate jazz, comedy and magic performances, the city offers many ways to woo. So whether your ideal date night involves wining and dining at one of Chicago’s most romantic restaurants or cruising down the river in a floating hot tub boat, these romantic activities for couples will help keep the sparks flying. RECOMMENDED: Find the best unique date ideas in Chicago

While the quality of the food is always important, a restaurant’s design and ambiance also play a big role in the experience. That’s why at the city’s most romantic restaurants, you’ll find stunning dining rooms, dim lighting, beautiful backdrops and other intimate touches that help spark love. A perfect date night may involve a comforting meal at an Italian trattoria, a lavish steakhouse feast or an evening in an unexpected place (who knew furniture stores had so much allure?). Whatever you prefer, the most romantic restaurants in Chicago are sure to set the stage for a charming and unforgettable time. RECOMMENDED: Discover the most romantic things to do in Chicago

Chicago’s meatpacking roots have made it a hub for beef for more than 150 years, and our steakhouses are some of the best in the world. Those looking for perfectly cooked filets and enormous porterhouses served with indulgent sides can visit old school institutions like Gene & Georgetti and Gibsons, while diners looking for more than just steak can get pristine seafood at Joe’s Seafood or Kindling. The city’s reputation as a haven for carnivores has also led to a boom in newcomers offerings traditions from around the world, like Bonyeon's Korean beef omakase and British Sunday roast at Hawksmoor. So whether you’re looking for wagyu by the ounce or steak frites, check out our guide to the best steakhouses in Chicago for a hearty meal. RECOMMENDED: Discover more of the best restaurants in Chicago

If you’ve been eyeing some of Chicago’s best restaurants, here’s your perfect excuse to finally try them out. Chicago Restaurant Week kicks off on January 24 at nearly 500 participating eateries in the city and suburbs, featuring everything from Michelin-starred restaurants to neighborhood favorites—all with special prix fixe menus at fixed prices. Winter in Chicago may be brutal, but our city’s cozy bars and restaurants and critically-acclaimed culinary experiences are worth leaving the house for. So get ready to brave the cold; here are this year’s best Chicago Restaurant Week deals. RECOMMENDED: Everything you need to know about Chicago Restaurant Week 2025

Fried chicken is one of the most comforting foods around, easy to share with a group alongside cornbread, mac and cheese and collard greens, but also worthy of a solo indulgence at any time. Chicago even has its own iconic version of the dish—served with mild sauce—and the city’s wide range of options means you’ll find numerous other spins, like Korean fried chicken at Crisp and Nashville hot chicken at Fry the Coop. It’s also on the menu at some of the best restaurants in Chicago, including glitzy steakhouses and Southern favorites. So prepare to get messy and satisfy your craving at the best restaurants for fried chicken in Chicago. RECOMMENDED: Discover more of the best cheap eats in Chicago

Chicago is a literary city—though often overlooked as such—and our many independent, locally-owned bookstores have long championed a bookish culture. Across the Windy City, residents value shopping local at Chicago gift shops, Black-owned businesses and indie bookstores that provide books as well as spaces for representation and identity. The following spots cater to every interest, from Spanish language children’s books to contemporary novels by BIPOC writers to LGBTQ history. Whether you like to read dog-eared, ripped pages of used books or shiny new hardcovers, you’re bound to stumble upon your great next read at the best Chicago bookstores. RECOMMENDED: Free things you can get with a Chicago Public Library card

More than ever, specialty and locally-owned gyms across Chicago know that accountability and a long-term commitment to training is easier with community, fun and recovery workouts. Many fitness clubs have transformed into holistic wellness centers with community-centered, cafe-like spaces, cold tubs and social outings outside of the studio. Whether a gym rat is looking for an old-fashioned solo experience, nurturing an interest in running, yoga and rest and relaxation, or on the hunt for a swolemate, places across the city offer classes and amenities for every type of goal. So start or continue your fitness journey at the best gyms in Chicago. RECOMMENDED: The best spas in Chicago

Sometimes, you just want a little escape from the city. If a weekend getaway isn't possible but you're still looking for new scenery and an adventure, there are plenty of options for a day trip within a few hours’ drive of Chicago. Spend an afternoon soaking up the rays on beaches along Lake Michigan, go hiking near Chicago in a state park or sample a variety of beers and cheeses up north in Wisconsin. The attractions are endless, ranging from amusement parks and Japanese gardens to museums and historic lighthouses. And the best part? Many of these destinations are also accessible by Metra. So get to planning with our guide to the best day trips from Chicago. RECOMMENDED: The most unique day trips from Chicago

Who says you need to escape the Midwest in winter? Any Chicagoan knows the dark months can be tough, but those who thrive don’t begrudgingly tolerate the winter—we embrace it. Within a few hours’ drive of Chicago, you’ll find towns, resorts and state parks with exciting, snow-forward outdoor adventures for the whole family like dog sledding, tubing and snowboarding, plus plenty of cozy indoor spots to lean into our Midwestern version hygge. Whether you and your family love to brave the elements or spend afternoons at bookstores, coffee shops and breweries, put on your layers, grab your snowshoes and get ready for fun. Here are the best winter getaways from Chicago. RECOMMENDED: The best day trips from Chicago

Baby, it's cold outside! When you're not shopping at Christkindlmarket or taking a spin on local ice skating rinks, warm up this holiday season with the help of some festive live music. Whether you're hoping to test your caroling skills with a sing-along at Millennium Park, catch Mariah Carey belting "All I Want For Christmas Is You" or watch the Joffrey Ballet's classic production of The Nutcracker, you'll find plenty of ways to celebrate Christmas in Chicago thanks to these holiday concerts spanning a wide variety of musical genres.  RECOMMENDED: Check out even more things to do for Christmas in Chicago

There’s no Chicago Christmas experience more authentic than bracing the chill of winter to cut down your own Christmas tree. Though Chicago offers plenty of dazzling light displays and holiday-themed experiences, you’ll need to head outside of the city for the perfect pine, spruce or fir. Whether you want to travel 30 minutes or two hours, there are plenty of spots ranging from muddy and rustic BYOS (bring your own saw) farms with house-made cookies and hot chocolate to elaborate, Instagram-worthy holiday backdrops and tractor rides. No matter what holiday movie you’re envisioning yourself in this season, you’ll enjoy holiday cheer and beautiful scenery while cutting down your own tree.  RECOMMENDED: Our complete guide to Christmas in Chicago

Hot people get eight hours of sleep, at least according to sober party organizer Daniela Cabada of Lez Get Together Collective. We come from a city of with an amazing bar scene, filled with breweries, wine bars and cocktail lounges, but today, many Chicagoans crave both social interaction and healthier lifestyles—and yes, sleep. As folks increasingly ditch dancing until dawn for reasonably scheduled, alcohol-free parties, Eventbrite says sober events in Chicago saw a 450% increase between 2021-2023, and an attendance surge of 771%. The popularity of these events and pop-up parties show that dancing, drinking, flirting and great music don’t necessarily have to go hand-in-hand with alcohol. So if you're looking for a good time sans drinking, here are the best sober parties in Chicago.

If your motto is the more saxophone the better, soak up the smooth sounds of Tim Warfield’s Jazzy Christmas show. Joined by a talented band of piano, trumpet, vocalists and more, the American saxophonist embraces the holiday classics you love with new interpretations. Sip a warming cocktail and enjoy the atmosphere at Jazz Showcase, one of Chicago’s most historic clubs. 

Feeling nostalgic? Lovers of 1970s folk and John Denver can relive the sights and sounds of late singer-songwriter while also enjoying cheerful Christmas tunes at the Rocky Mountain High Experience: A John Denver Christmas. Step into the Broadway Playhouse at Water Tower Center for tribute singer Rick Schuler’s set of iconic Denver songs, like “Take Me Home Country Roads” and “I’m Leaving on a Jet Plane,” and interpretations of the singer’s renditions of “Joy to the World” and other festive songs.

Candlelight concerts are the ultimate multi-sensory experiences for intimate, romantic evenings year-round. This holiday season, listen to string quartets in the glow of thousands of candles at festively decorated venues across the city, including Stan Mansion, Music Box Theater and St. Luke’s Episcopal Church. Classical music may not be your go-to genre, but hearing live carols with string instruments, Christmas soundtracks on piano or a medley of holiday favorites like “Carol of the Bells” and “December, 1963” will have you swooning.

A lot of song and a little dance: Experience upbeat jazz and exhilarating tap dance performances at the Chicago Human Rhythm Project (CHRP)’s annual Holiday Rhythms concerts. Groove to invigorating holiday beats from artists Jumaane Taylor, Stone Soup Rhythms and the Eric Hochberg Trio featuring Dee Alexander. The show is filled with music, dance and joy—and even a complimentary drink and dessert bar so get ready for a holiday celebration (and accompanying treats) like no other. Proceeds benefit the CHRP Mayfair Arts Center, an arts incubator-education space.

Chicago’s favorite German-style outdoor holiday market is more than just a delightful place to snack on stinky cheese (technical term: raclette), shop for European-made trinkets and warm up with glühwein. Each year, Christkindlmarket also features heartfelt performances by groups like the Mother McAuley A Cappella Choir, various children’s choirs and Phenix Trio, a group famed for getting audiences to sing with them. So sing along, smile and enjoy the cheer amongst the sparkling holiday decor.

Holidays, but make it gay: That’s what Chicago Gay Men’s Chorus’s annual concert does best. This year, the 200-person choir’s show Totally ‘80s HoliGAY takes you back to the sparkliest decade. Immerse yourself in the action-packed, dance-filled performance featuring neon lights, big hair and unforgettable 1980s favorites. Whether you’re craving heart-pumping holiday cheer or can’t get enough of retro vibes, you’ll be tapping along to tunes—and maybe even singing along yourself. 

Gezelligheid is a Dutch word that loosely translates to “cozy,” and as the darkest days approach, any Chicagoan knows we need all the comfort we can get. Award-winning singer-songwriter Andrew Bird conjures the sentiment in his 14th annual Gezelligheid concerts at Fourth Presbyterian Church, a holiday concert tradition aiming to bring us together with cheerful, moving music. With a mix of instrumental violin, Victrola horns and other instruments, expect holiday favorites, Bird’s classic hits and songs from his latest album Sunday Morning Put-On.

The Loop’s National Historic Landmark Orchestra Hall is ornate enough to dazzle year-round, but shines extra bright for the Chicago Symphony Orchestra’s Merry, Merry Chicago! holiday concert conducted by Alastair Willis. On a stage decked with—literally—boughs of holly, larger-than-life red bows and wreaths, the acclaimed instrumentalists play tunes ranging from beloved holiday favorites to Christmas in Chicago, a local treasure. Before the show and during intermissions, you’ll even hear pop-up performances from Chicago school choirs and community ensembles throughout the halls.

There’s no better place in Chicago for holiday cheer than under Millennium Park’s Cloud Gate (a.k.a. "The Bean"), where like-minded exhibitionists delight in shared songs amidst the twinkling lights of the city Christmas tree and the sounds of laughter from nearby ice skaters. With some hot cocoa in your hand, join local choirs and bands as they lead attendees in a powerful sing-along of joyful holiday carols. This year, the series takes place Fridays at 6pm from December 6-20, with a different choral group highlighted each week.

For the 41st year, Southport Corridor’s favorite historic theater brings three weekends of Christmas singing followed by a double feature of classic holiday films to Chicago’s North Side.  Sit back in plush theater seats with snacks and drinks as you belt “Rudolph the Rednosed Reindeer” and “It's Beginning to Look a Lot Like Christmas,” and just when you’ve worn yourself down, stay for a showing of White Christmas and It’s a Wonderful Life.

Bringing much needed plant-based sabor to the River North neighborhood, plant-based dinrers can step into this bright, intimate space covered in colorful murals and enjoy Mexican staples. Penelope’s Vegan Taqueria’s fully-vegan menu includes tacos, enchiladas, molletes and other small bites. For brunch, grab the chilaquiles and coffee—there’s bar seating available if you’re dining solo, while small groups can snag one of the tables.

Lucy’s Cafe is great any day of the week, but it holds a special charm on slow, cheerful weekend mornings spent with family and friends. The extensive menu of American-style breakfast is exclusively vegetarian, and  most items can be prepared vegan upon request. Order standout dishes like vegan waffles or the southwest skillet—a medley of veggies, plant-based meat, black beans and cilantro—and grab a seat on the sunny front patio when weather allows.

Last summer, Chicago couple Emma and Blair Sheade were celebrating their one-year anniversary with a camping trip. Though they’re frequent campers, they jokingly refer to themselves as amateurs because they always seem to forget something or have trouble starting their campfire. On that particular trip, “everything that could go wrong, went wrong,” says Emma. She went to bed that night thinking that there must be an easier way for people to camp. And if there were, perhaps more people would want to do it. That was the genesis of Pitch, the pair’s recently-launched on-demand camping concierge service catering to Chicagoans who want to experience nature, but might not have the tools or time to organize a camping trip on their own. Emma considers Pitch to be an authentic outdoor experience that provides a middle ground between traditional, do-it-yourself camping—which can be intimidating to novices—and the often pricier glamping. When you book a night with Pitch, the service sets up your campsite and stocks it with the essentials—a tent, sleeping pads and bags, a lantern, a welcome cooler stocked with essentials, water, snacks, games and a fire log—and tears it all down after you leave. If you have questions about the area or the equipment during your stay, a “scout” is on-call to help you. Outdoor recreation has become extremely popular as a safe and easy travel option throughout the pandemic, but it’s still not as easy an option as it could be. “So many people want to try [ca