Your Chicago dining guide, upgraded

More than 55 million people visited Chicago in 2024. I was one of them. Just 90 minutes away via my favorite mode of transportation, Amtrak, I may have made the trip once a month for the last few years. And in the last year, I visited many splurge-worthy favorites that brought me so much joy. Chicago has a magical feel — fantastic food, the river and lake to explore, and incredible people who call it home. It pulls you in.

And don’t let the weather scare you. Chicago is truly a city for all four seasons. I’ve spent spring afternoons, summer weekends, winter nights and fall days wandering around, dining at restaurants that blew me away, and, of course, people watching.

So if Chicago is on your travel bucket list, here are the accommodations, standout restaurants, and activities to add to your itinerary. This list barely scratches the surface of everything the city offers, but it highlights fine dining, once-in-a-lifetime meals and luxury experiences — a little pizazz to go alongside the Chicago staples you probably already know.

Sushi Restaurants

Sushi San – Sushi San impresses with its consistency — both in food quality and in customer service — across all three of its Chicago locations. The Lincoln Park outpost, the most recent one I visited, is airy, welcoming, and even offers brunch.

The brunch menu mixes sweet and savory, with standouts like fluffy Japanese pancakes with matcha butter and a miso salmon benedict served on a crispy rice “waffle.” The benedict wasn’t my personal favorite, but it’s a playful, memorable twist I know many will love.

Lincoln Park also offers one of the best midday deals in the city: a $38 lunch tasting menu with edamame, spicy tuna crispy rice, sashimi and nigiri, a scallop hand roll, and more. For dinner — or when you want to truly go all out — order the Megatron. This three-tiered showstopper arrives stacked with 12 pieces of nigiri, 12 pieces of sashimi and two maki rolls, all spotlighting premium fish.

Omakase by Kanemaru – For a more intimate and indulgent sushi experience, head to Omakase by Kanemaru. Tucked on the second floor, the restaurant offers just ten counter seats and two to three seatings a night. It’s the kind of setting where you can interact with the chef, watch each piece of nigiri come together, and savor the craft up close.

As the name promises, the menu is strictly omakase — and my favorite kind at that: pristine, high-quality nigiri. I’m a lover of all kinds of raw fish, but the precision and freshness here stood out in every bite. This isn’t about flashy sauces or rolls; it’s about letting extraordinary fish and seafood shine in their purest form. The meal ends simply, with matcha ice cream, a quiet, sweet finish that left me smiling all the way to my hotel.

Jōtō Sushi – Inside CH Distillery — the home of Chicago’s infamous Malört — you’ll find Jōtō Sushi. It’s a rare spot that excels at both minimalist nigiri, where the fish is the star, and saucy, more elaborate rolls. Pulling off both styles well is no small feat, but Jōtō does it beautifully. The restaurant has a lively energy, with giant shutters that create an indoor-outdoor vibe and a patio perfect for warm evenings.

The cocktails are just as memorable. The lychee martini was so balanced and bright that nearly everyone in my group ordered it more than once.

What truly sets Jōtō apart is its in-house dry-aging program, which elevates the fish to a whole new level. My friend put it best after tasting the dry-aged bluefin tuna set — featuring akami, chutoro, and otoro: “When I tell you this was the best platter of sushi, from best to bestest, it was. All tens.” If you’re lucky, you might also catch them grilling kushiyaki, skewers of meat and vegetables that add a smoky flourish to your meal.

Lawrence Fish Market – My favorite budget friendly sushi spot recently opened a new location in Chinatown. Unlike the original Lawrence Ave location, there’s plenty of seating, so you can dine in and enjoy your meal. They serve classic rolls, sashimi, nigiri and their signature rolls, in addition to ramen and starters. But if you’re taking food to go, their sushi platters can feed a crowd and are delicious.

Experiential Dining

Esmé – Experiential dining, the likes of which Esmé specializes in, has my name written all over it. While the food is certainly the main focus, your experience at Esmé is designed to be so much more than that. It’s almost likely you’re stepping into a unique art museum, where you participate and enjoy the art — which covers the wall, informs the plates, and fuses with the food — creating a narrative that you won’t forget anytime soon. Even the music fits the theme for a fully immersive experience. The one-Michelin-starred restaurant changes its menu and artists quarterly, so you’ll have a completely different experience the next time you dine, if you choose to do so. For lefties like me, let the waiter know, and they will bring out silverware that’s angled specifically for us. If a full multicourse tasting menu isn’t what you’re looking for, Bar Esme offers a more relaxed environment with wonderful drinks, small bites, and a seasonal three-course prix fixe menu.

Daebak Korean BBQ – Open late and always buzzing, the Wicker Park location of Daebak BBQ serves up sizzling meats, plentiful banchan (Korean side dishes), and hearty soups and stews — all to the soundtrack of loud K-pop. Owner and chef Namhee Kim is often right in the mix, grilling at tables, delivering plates, and chatting with diners. The aroma alone will pull you in, and the food is absolutely worth slowing down for.

Daebak doesn’t follow the all-you-can-eat model, but instead offers thoughtful packages that pair different cuts of meat with banchan and sides. From there, you can supplement with whatever else catches your eye. The staff grills the meat for you — perfectly, every time — then cuts it into bite-sized pieces so it’s ready to share.

It’s a fantastic date-night spot, but Korean BBQ really shines with a group. I loved it so much on my first visit that I was back again with friends soon after.

Duck Sel – Duck Sel is a multi-course tasting menu pop-up that serves incredible food infused with a good dose of whimsy. The brainchild of Chef Donald Young, the come-as-you-are restaurant is a great gateway for those who find traditional fine dining intimidating or stuffy. You’re seated at tables with other diners, there’s no dress code, and while the food is certainly fine dining, it’s more than that. Chef Young incorporated nostalgia into every course, including the drink pairings, which are also available in non-alcoholic options. There are adorable ducks of every size and variety covering the walls, on the table, in the bathroom, and woven throughout the meal for a playful twist. Every detail is thoughtfully curated for one hell of an experience you won’t forget.

Steak and Seafood

RPM Steak – RPM Steak is a classic two-story steakhouse with high ceilings, a marble bar, and black wood tables, complemented by upholstered white chairs. Steaks are the name of the game here, with at least 16 different options, including 28-day dry-aged, Australian and Japanese wagyu and kobe beef. My steak was cooked perfectly and complemented by the numerous sides, which include hen of the woods mushrooms, Japanese sweet potato and hand-cut black truffle fries. Don’t skip the seafood, either, which is fresh and delicious. The service certainly matches the price point, our waiter was incredibly attentive, to the point that I thought he was the general manager for the first half of our meal.

Tango Sur – For delicious steak that won’t break the bank (at least when compared to Chicago’s pricey steakhouse lineup), you’ll want to visit Tango Sur. The Argentinian steakhouse is dimly lit and stays busy, with outdoor seating, if that’s your preference. The menu includes tabletop grills piled high with grilled short ribs, flap meat, sausage, beef sweetbreads, black sausage, and other deliciousness. The rest of the menu is just as impressive, featuring Argentine empanadas with a variety of fillings, provoleta — a gooey roasted cheese — pastas, prosciutto served with melon, and multiple potato sides. Folklore, from the same owners, is their sister restaurant with a menu that has a lot of crossover if that location is more convenient.

Legal Seafood – If you’re looking for dinner with a view, Legal Seafood certainly delivers. Overlooking the Chicago River, the seafood restaurant offers the expected raw bar, fish plates, lobster roll and fish sandwiches. The oysters were wonderful and would certainly bring me back. As for the rest of the menu, while flavor is usually my preference, the simply prepared seafood is the way to go. For a similar view but focused on steak rather than seafood, and the same excellent oysters, try Smith & Wollensky next door.

Brunch

Dell Rooster -Dell Rooster is one of those brunch spots where every bite feels like a promise for more — you might even want to come back for dinner. The colorful space, dominated by a giant rooster mural and pulsing with salsa, draws inspiration from across Latin America and the Caribbean. At the helm is Miguel Tenesaca, an Ecuadorian immigrant who honed his craft in kitchens throughout Chicago.

The brunch menu is extensive and playful: warm stuffed dates with goat cheese, romesco, bacon and black garlic aioli; Rooster & Waffles, the restaurant’s spirited take on the classic chicken-and-waffle; and a short rib skillet with crispy potatoes, peppers, onions, queso fresco and charred tomato-guajillo sauce. It’s hard to go wrong here, and while brunch is the star, I’m already looking forward to returning for dinner.

Where to Stay

Nobu Hotel – Located in the West Loop near Fulton Market, the Nobu Hotel offers a striking contrast to many of Chicago’s popular hotels, with a minimalist Japanese design meant to promote tranquility. It’s a balanced take on modern luxury: rooms feature blonde wood floors, soft lighting, low platform beds, and floor-to-ceiling windows, perfect for slowing down and rejuvenating. The hotel continues the theme with a 40-foot indoor “tranquility” pool and steam rooms — a serene, modern and indulgent retreat.

Inside, the iconic Nobu restaurant serves breakfast, lunch, and dinner, blending Japanese and Peruvian flavors under the direction of Chef Nobu Matsuhisa. The menu dazzles with sushi, A5 wagyu, and creative mains. Standouts include the world-famous spicy tuna crispy rice, Miso Black Cod, and seafood-filled “tacos.” As expected, the experience comes with a premium price tag — though the $75 all-you-can-eat weekend brunch offers a more approachable way to taste Nobu’s celebrated dishes.

Pendry Chicago – On Michigan Avenue, right in the heart of the action and within walking distance of the Magnificent Mile, sits Pendry Chicago, a luxury boutique hotel boasting two Michelin keys. Housed in the 1929 Art Deco Carbide & Carbon Building, the hotel’s dark stone and gold-trim exterior is instantly striking. Check-in can take a little time, as the hotel stays busy — something to factor in if you’re making dinner reservations like I did.

Our spacious room featured a wonderfully comfortable bed (the most important detail in my book) and a large bathroom, though the shower was surprisingly small in comparison.

Things to Do

Chicago Boat Company – There’s nothing quite like an afternoon on the Chicago River. Surrounded by stunning architecture and the gentle breeze, you can watch other boats drift by while enjoying your own adventure. The Chicago Boat Company offers a range of rentals to suit your mood: hot tub boats in the winter (romantic but a little tricky to navigate), retro boats in the summer, or larger vessels like yachts, duffies and pontoons if you’re with friends.

The Peggy Notebaert Nature Museum – Just minutes from Lake Michigan, the Peggy Notebaert Nature Museum is packed with educational fun. Morgan and I came mainly for the butterflies and the third-of-a-mile nature trail that circles the museum. The trail feels like a hidden urban oasis, secluded yet right in the middle of everything. Inside, a 2,700-square-foot greenhouse is home to over 1,000 butterflies, perfect for wandering on a rainy afternoon—or really any afternoon.

Tricoci Salon & Spa – I have big, curly hair, so I know a thing or two about haircuts. The best one I’ve ever had? Tricoci Salon and Spa — and I’m not exaggerating. It might have ruined me for all future haircuts. Beyond hair, Tricoci offers massages, facials, manicures, and more, making it a one-stop shop for any self-care you need.

Garfield Park Conservatory – On a rainy or chilly Chicago day, there’s no better escape than Garfield Park Conservatory. Free for Chicago residents (and $10 for everyone else), the conservatory spans 2 acres indoors and 10 acres outdoors, open year-round. Inside, the gardens are divided into houses highlighting different plants and climates — from the Palm House with over 70 palms, to the fern room, to the desert house filled with cacti and succulents.

With Besties

Chicago is a great city to visit with friends. There’s so much to do, so much to eat, and what better way to do it than with your besties? I planned a quick weekend getaway with a few of my friends, and here’s some of what we did and ate.

Tanta – Located in River North within easy walking distance of many hotels, Tanta is a Peruvian restaurant with a killer rooftop and an even better playlist. Morgan and I went for brunch and immediately knew we had to return for dinner. Brunch was incredible, with classic Peruvian dishes alongside inventive twists on brunch favorites.

Dinner on the rooftop was a feast. We savored Apaltado, a delicate raw salmon dish with jalapeño-avocado, chili oil, cherry tomatoes, and a tapioca cracker; Nikkei, a beautiful tuna ceviche with tamarind leche de tigre and avocado; and the full branzino, butterflied with head on and draped in ají amarillo meunière sauce. Honestly, you can’t go wrong here.

Big Bus Tour – If you travel like me, you have a packed itinerary with loads of fun, great food, and not a whole lot of downtime. You’re on vacation, every minute counts, right? When I need some downtime, I look for activities like the Big Bus Tour. The open-air double-decker bus makes a loop around the downtown Chicago area, giving you a chance to see the sights, get familiar with the area, and take a well-deserved break. And when you’re ready to hop off, you can do that, and get right back on for as long as your ticket allows.

Seadog Lakefront Fireworks Cruise – Normally, fireworks aren’t my thing — all the loud bangs and commotion can be overwhelming. Chicago, however, does it right. Every Wednesday and Saturday from Memorial Day through Labor Day, Navy Pier hosts a fireworks show. The Seadog Lakefront Fireworks Cruise takes you out into the harbor for a speedy, exhilarating boat ride, then positions you perfectly for an unbeatable view of the display. Even my skeptical self was impressed.

Great Big Game Show – My wife and I love game shows for their low-stakes, comforting fun, so discovering the Great Big Game Show was a no-brainer. Teams of friends or strangers compete in trivia, speed challenges, blocks, and, of course, a giant wheel. The live host keeps energy high and cracks jokes, while short video clips capture the best moments for everyone. Laughter, friendly competition and a highlight reel? Win-win.

Pro tip: Grab brunch at Beatrix in the same shopping mall before your visit. The coffee is excellent, service is quick and friendly, and this location doesn’t have as long a wait as the River North spot. I’m particularly a fan of the hot honey fried chicken sandwich.