Chicago always has something to prove. When it went up against New York for the 1893 World’s Fair, a New York Sun reporter called out its “windbag” campaigners. Illinois ended up hosting the fair, and Chicago embraced its new identity as the Windy City. That chip-on-the-shoulder energy still defines this metropolis, a city that builds, innovates, and competes like it has everything to lose.

Chicago’s tech scene is a diverse landscape that shouldn’t be slept on—but you probably know that. The Second City’s tech sector has grown by 18 percent over the past decade, adding more than 106,000 direct jobs and nearly 150,000 indirect jobs, according to the Chicagoland Chamber of Commerce. The city’s universities produce more computer science graduates than anywhere else in the US. Giants like Google, Salesforce, and Meta have satellite operations here, while startups like Tegus, Uber Freight, and G2 have relocated from Silicon Valley, drawn by Chicago’s talent pool and affordable cost of living.

Chicago’s tech scene is not siloed; nearly half of all tech positions are tied to core industries like health care, finance, and logistics. Last August, the TechChicago conference spotlighted quantum computing, energy-efficient data centers, and equitable access to capital, demonstrating that Chicago is thinking about how technology can enhance everyday life.

To be in Chicago is to work hard, play harder. Dinner in Fulton Market, drinks on the Riverwalk, and a comedy set to close out the night.

Where to Stay

While Chicago’s tech scene spans the city, chances are your work trip landed you somewhere in the Loop, River North, or West Loop area. Our lodgings keep you close, comfortable, and surrounded by fellow professionals.

363 E. Wacker Drive, (312) 787-3447

Where the Chicago River and Lake Michigan meet, the St. Regis delivers the city’s pinnacle of luxury, complete with a world-class spa, fitness facilities, and acclaimed dining. The Signature Butler Service takes care of unpacking, suit pressing, shoe shines, and morning coffee (or tea), so you can focus on the business that brought you here. A complimentary house car can get you to nearby meetings or lunches within a 2-mile radius. Start with the Tokyo Breakfast at Japanese restaurant Miru, return at 5 pm for the hotel’s daily champagne sabrage, then head to Tre Dita for handmade pasta and Tuscan wood-fired steaks—be sure to reserve ahead.

200 N Green St., (312) 761-1700

If you want a hotel that feels like part of the city, it’s the Hoxton in the West Loop. Check in and out anytime when you book directly. Workspaces are available, from library desks to coworking spaces and meeting rooms. If you’re hungry, the on-site café serves Aya Bakery pastries and coffee, and if you need a break, daybeds await, which are ideal for a power nap or nursing a hangover. Weather permitting, their outdoor terraces double as another place to get work done. You don’t even have to leave the Hoxton to hit the neighborhood’s hottest dining and drinking spots; Cira serves Mediterranean-inspired eats all day, Cabra Cevicheria dishes Peruvian bites on the rooftop, head downstairs to Lazy Bird for cocktails and live music Thursday through Saturday, and Milk Bar is also in-house for a late-night sugar fix.

Courtesy of The Emily Hotel

311 N Morgan St., (312) 764-1919

In Fulton Market, the Emily Hotel is perfect for travelers who want a local vibe with all the luxuries and tech conveniences. Grab a coffee at the in-house coffee bar, lunch at Fora, cocktails at rooftop bar Selva, and dinner at Sushi by Bou. Stay active in the 24/7 fitness center, and if the weather permits, catch a film at the hotel’s terrace cinema.

900 E Grand, (872) 710-5700

At Sable, you’ll have everything you need for an enjoyable stay. Grab a coffee in the lobby at Kisbi, where single-origin beans from Costa Rica, Kenya, and Ethiopia make your morning feel instantly richer. Lirica, the Spanish- and Iberian-inspired restaurant, is perfect for a solo lunch or team dinner. The Offshore Rooftop has unbeatable views of the skyline and Lake Michigan, plus a full-service bar. As for amenities, there’s a 24-hour fitness center, meeting rooms if you need to get work done, and, of course, Navy Pier itself just outside your door—full shops, restaurants, and attractions to keep you entertained. It’s a bit like living in a mall.

Courtesy of InterContinental Chicago

505 N Michigan Ave., (312) 944-4100

In the heart of the Magnificent Mile, the InterContinental blends big-city business energy with old-school glamour. That’s partially thanks to its indoor pool, a 1929 stunner tiled in Spanish Majolica and watched over by a terracotta Neptune fountain, floating 14 stories above Michigan Avenue. During the week, you’ll mostly see business travelers, though families often stay here, too. The practical amenities are covered, including meeting rooms, printing services, and even a notary. There’s a Starbucks in the lobby, but with so many better local cafés nearby, it’s worth wandering out.

Where to Work

You can work from any of the hotels on our list, but if you need a change of scenery, Chicago has plenty of coworking options, too. Below are some of our favorites, and Deskpass is a great resource for more options.

Photograph: Steve Geer/Getty Images

20 N. Wacker Drive, 12th Floor

Inside the Civic Opera Building in the city’s business district, this 60,000-square-foot workspace is designed for tech professionals. Fast Wi-Fi, ergonomic setups, meeting rooms, and even a rooftop terrace and fitness center. Drop in for $35 a day on Deskpass.

3130 N Rockwell St.

In Avondale, Guild Row offers a sunlit workspace with high ceilings, private Zoom booths, and a café and bar for breaks. The Belmont Room hosts workshops, talks, and events, but the overall atmosphere is calm and focused for getting work done without distractions. It’s a space to recharge, meet like-minded people, or settle in for a productive day. You can purchase a day pass for $28.

1821 W Hubbard St Unit 209

In the West Loop, Art/Work Coworking is a creative lab that draws in the city’s creatives, techies, and freelancers. Open 24/7 with automated access, it offers desks and bookable meeting rooms. Drop in with Deskpass, or book a conference room starting at $50 an hour.

Where to Get Your Coffee

112 N Green St.

If you need a reliable off-site work spot, Sawada Coffee has plenty of seats, strong Wi-Fi, and strong coffee. Founded by Japanese barista Hiroshi Sawada, Sawada Coffee is renowned for the Military Latte—a rich jolt of matcha, espresso, and cocoa—but they also have cortados, cappuccinos, and cookies on hand to keep the workflow steady.

714 N Wells St.

Owned by Palestinian American friends, Oud Coffee is a River North favorite for craft lattes and bites. The signature Oud latte blends pistachio syrup, cardamom spice, and fresh mint, while the menu also includes Turkish coffee, tea, and smoothies. Snack on Manakeesh flatbread, stuffed dates, or baklava. Spacious indoor seating makes it a solid spot to catch up on work, or sit outside if the weather permits. There’s another location in Wicker Park, should you find yourself closer to that neighborhood.

5531 N Clark St.

The Understudy is a theater-bookstore-slash-café, with passion fruit syrup on offer alongside lavender, wild rose petal, and hazelnut. Non-coffee drinkers can sip iced ube lattes, sparkling matcha lemonades, or a lychee roasted goddess tea. Come for the flavor, stay for the creative atmosphere, with light-filled nooks that make it easy to lose an afternoon.

3101 S Morgan St.

Bridgeport Coffee has been roasting on the South Side since 2004, and it’s still one of the city’s best stops for a cup of coffee that actually tastes like where it came from. The shop sources beans directly from growers, cutting out middlemen for better flavor and fairer trade. There are only a couple of counter seats and a handful of tables, but it’s a cozy place to work if you snag a spot.

Where to Eat

Chicago’s hottest eateries are often booked solid, but we’ve found the sweet spots that actually have availability.

Courtesy of Day Off Group

932 W Fulton St.

At Rose Mary, a Chicago native and Top Chef winner brings together Italian and Croatian cuisines in what he has dubbed “Adriatic drinking food.” The menu changes with the seasons, but the zucchini fritters with pesto aioli, the tuna crudo, and the radiatore cacio e pepe feel almost nonnegotiable when I go. Beyond the trifecta, you can expect bold takes on fish, meats, pasta, and risotto. The dining room is almost always full and buzzing, which makes it a lively choice for a business dinner or post-work meal that turns into another round of drinks.

2534 N Milwaukee Ave.

For business travelers craving pasta, Mano a Mano is a must. The tagliatelle bolognese and bucatini cacio e pepe are heavenly, but every pasta dish is worth tasting, from the stuffed farfalle to lobster ravioli and short rib ravioletti. If your schedule allows for a Sunday reservation, Spaghetti Sundays are a treat: $45 per person gets you a curated lineup of antipasti, an argula Caesar salad, a pasta dish, and gelato to finish. It’s a perfect place for entertaining clients or recharging with coworkers after a long day.

800 W Randolph St.

At Au Cheval, Chicago’s über-celebrated burger joint, the melty, egg-topped cheeseburger lives up to its hype. The vibe is low-key, with a diner-meets-French-speakeasy feel, featuring dim lighting, leather booths, and an open kitchen that’s always at full capacity. You have to get the cheeseburger, but the chilaquiles and roasted bone marrow are also worth ordering. There are no reservations; swing by on a weekday afternoon, put your name down, and grab a drink at one of Fulton Market’s bars while you wait.

2542 N Milwaukee Ave.

Andros Taverna has a menu of seafood that rotates daily to feature the freshest catch. If you don’t like seafood, the contemporary Greek restaurant’s locally sourced lamb is dry-aged, butchered in-house, and grilled over charcoal for a smoky finish. Every dish is served family-style, so it’s an ideal spot to share with colleagues or clients in a convivial setting that feels upscale without being stuffy.

Courtesy of Day Off Group

1110 W Carroll Ave.

Chef Joe Flamm’s latest venture, Bar Tutto, has become an all-day hot spot for Chicago’s working crowd since it opened last December. It’s perfect for catching up on emails, meeting a client, or unwinding after a workday. Start your day here with a crafted latte, flaky pastry, or a hearty egg wrap to power through the morning. By lunch, this place hums with people ducking in for salads, sandwiches, and bowls of homemade pasta. Come evening, when the laptops disappear, the space shifts into a relaxed dinner scene. Italian-inspired cocktails, a thoughtful wine list, and shareable plates. Make sure to order the Bavette steak, served with peperonata sauce, crispy frites, and a smoky garlic aioli.

630 W Lake St.

At Kumiko, chef and mixologist Julia Momosé has created one of the city’s most inventive drinking and dining experiences. The intimate Japanese dining bar is best known for its meticulous cocktails and sake list. You can stop in for drinks and order from the seasonal à la carte menu, or settle in for the tasting menu, where dishes arrive with curated cocktails, sake, or spirit-free pairings that are just as creative as the alcoholic ones. Downstairs, a separate weekend bar spotlights whiskey and shochu. It’s an even cozier hang that regulars recommend for marking a special occasion.

Courtesy of Day Off Group

1045 W Fulton St.

Il Carciofo is a Roman-style Italian restaurant with a seasonal menu that rotates through antipasti, pizzas, and hand-rolled pasta. The dining room channels a moody trattoria, with an open kitchen—a signature move at Joe Flamm’s eateries—where you can watch the cooks turn out plate after plate. If you order one dish, make it the rigatoni alla carbonara, but it’s hard not to over-order here. And after a hearty meal, the dessert lineup offers gelatos and sorbets for a refreshing reset. If you’re still in the mood to indulge, there’s always a tiramisu.

214 W Erie St.

Asador Bastian isn’t your typical Chicago chophouse. With Basque-inspired decor and a menu to match, the specialty is Txuleton beef—thick, bone-in steaks from mature cattle, served by the pound. But don’t overlook the seafood, which appears to be just as flavorful. I haven’t been myself, but I hear the bone-marrow potato purée is to die for. It’s a reliable pick for client dinners when you want the ambiance to impress as much as the food.

1202 W Grand Ave.

The space at Elina’s is intimate and candlelit, but the food is bright and inviting. The menu is classic Italian American comfort food with enormous portions. Order the Caesar salad, the chicken parmesan, and the rigatoni alla vodka—which is topped with crunchy, Calabrian breadcrumbs. Though the dining room is cozy, its shareable plates make it a delicious choice for a team dinner.

Courtesy of Chef’s Special

2165 N Western Ave.

For a kitschy yet upscale take on the American Chinese takeout you grew up on, Chef’s Special delivers saucy, family-style classics. Think orange chicken, Mongolian beef, and lo mein noodles—fast. The nostalgic comfort food is paired with tropical cocktails, from a lemongrass gimlet to an $8 shot-and-beer combo. Ideal for small teams or clients, the menu encourages sampling, making it less about individual plates and more about the experience.

700 N Clark St.

Ambar is inspired by the communal Balkan tradition of “Voz,” where food is brought out to the table in a continuous procession. For a set price, you can order from more than 40 Balkan dishes. Grilled meats, slow-cooked seafood, stuffed pies, cheesy flatbreads, creamy spreads, and desserts I keep coming back for. Everything comes in small plates, so you can order seconds (or thirds) of your favorite dishes without shame. For visiting execs, the all-you-can-eat model is a chance to entertain colleagues without the hassle of menu math, and the abundance keeps the conversation flowing.

Courtesy of Zarella

Ask any Chicagoan, and they will insist that Chicago’s preferred pizza style is actually a crispy, tavern-style pie. But if you must try deep-dish pizza, skip the touristy Lou Malnati’s and get Pequod’s instead. For Chicago-style pizza, some local favorites are Paulie Gee’s, Professor Pizza, and—my favorite—Zarella Pizzeria & Taverna, which offers both thin artisan and tavern-style pizza. If you manage to snag a reservation, order the Spicy Vodka pizza, the gooey mozzarella sticks, and the pineapple brown butter cake. You can thank me later.

Portillo’s is for tourists. If you want a real Chicago dog, head to Superdawg or the Wieners Circle.

Where to Drink

Chicago drinks hard. Survive your first Malört shot at the stickiest dive bar you can find, then check out the city’s barcades and breweries, where you can unwind, catch up with colleagues, or just enjoy the city.

Courtesy of Goose Island Salt Shed Pub

1221 W Blackhawk St.

I love grabbing a drink at the Goose Island Pub before catching a show at the Salt Shed. On sunny days, the riverside patio and skyline views are so serene. Inside, it’s industrial but comfortable, lively enough to still feel connected to the city. The tap list mixes Goose Island classics with experimental brews, barrel-aged bourbon, and seasonal rotations. Goose Island’s main taproom in West Town is also worth a visit if you’re in the area, but the Salt Shed venue has a built-in concert ambiance that makes it the perfect pregame joint.

213 W Institute Pl.

Downtown Chicago doesn’t overflow with true barcades, but Headquarters Beercade scratches the itch. The draw is the dozens of arcade cabinets and a decent lineup of Stern pinball machines, all on free play, yet the vibe skews more corporate happy hour than underground gamer hangout. If you want to sip on craft beer while mashing buttons on Street Fighter II, this is the place.

839 W Fulton Market

With three locations across the city, you won’t have to go far to find Emporium. Wicker Park is usually the busiest, and the West Loop location is a perfect stop before dinner at Au Cheval. Expect skee-ball, pinball, and pool tables running on tokens, plus a drink menu that rotates in local brews and seasonal hard kombuchas. Don’t count on every machine working, but Emporium is less about high scores and more about blowing off steam over a beer; the games are just a bonus.

3540 N Clark St.

Sluggers has been a Chicago staple for over 35 years. With over 40 TVs streaming games, and walls stacked with sports memorabilia, it’s the liveliest sports bar in the city. Upstairs, you’ll find batting cages, skee-ball, and other arcade games.

2833 N Sheffield Ave.

Replay in Lincoln Park is a dive-bar-meets-party with a lineup of rotating craft beer and cheeky cocktails like “Shrek Is Love” and “Not My Gumdrop Buttons.” Most arcade games are free to play, with the newest Stern machines reasonably priced. There’s always a theme that leans into ’90s nostalgia, and weekend DJs keep the energy high. The crowd is cool, diverse, and unmistakably Midwestern. This is reviewer Louryn Strampe’s go-to spot for pinball and beer before catching a show.

Where to Giggle

You haven’t really done Chicago until you’ve laughed through its comedy scene, home to the legends of both stand-up and improv.

Courtesy of Second City

230 W North Ave.

Second City is the birthplace of improvisational comedy, not to mention that it has launched more SNL cast members than you can count (Dan Aykroyd, Tina Fey, Bill Murray, Amy Poehler … I can go on). You can’t go wrong with the mainstage show, but the lineup branches out into family-friendly matinees, late-night experiments, and seasonal sets. If one show sells out, there’s always another around the corner—literally, the venue runs multiple stages at once.

1548 N Wells St.

Zanies is as classic as it gets for stand-up, where legends and up-and-comers share the same tiny stage. It has a low-ceilinged, brick-wall intimacy that feels exclusive. On weekends, you might catch a touring comic; on weeknights, it’s roast battles, showcases, and the kind of rowdy energy that feels more underground than you’d expect from a venue this iconic.

3175 N Broadway

Sure, this isn’t the OG comedy club on Sunset Boulevard, but Chicago’s Laugh Factory has carved out its own scene. The vibe is more Midwestern grit and quick wit, and the rainbow-arched stage is just as legendary in person. The “Chicago’s Best Standup” nights rotate through the city’s local comics, and you never know when a bigger name will drop in unannounced. You’ll also find open mics and themed shows that keep nights unpredictable.