The Chicago Playbook

Brendan Sodikoff's dim, jazz-soaked steakhouse has been nearly impossible to get into since 2012 — leather booths, vinyl on the turntable, dry-aged steaks broiled hard. It lands on national best-of lists every year and still feels like a secret when you're in it. The Splurge dinner in this Playbook.

Reservations: Resy — tables drop 21 days out at 9 AM sharp; prime weekend slots vanish in minutes, so set an alarm for your game weekend

The world's first Filipino restaurant to earn a Michelin star, and promoted to two stars in the 2026 Chicago guide. Genie Kwon and Tim Flores run it as a casual bakery by day and a tasting room by night. The city's hardest table, and worth every minute of the scramble.

Reservations: Dinner opens on a rolling six-week calendar at noon and is gone almost immediately; the daytime café is walk-in only (expect a line)

Top Chef finalist Sarah Grueneberg won the James Beard Best Chef: Great Lakes award here in 2017, and the handmade pastas are rolled and cut in-house daily at the open pastificio counter. It's a West Loop institution now, and one of the best pre-game dinners in the country given how close it sits to the action.

Reservations: Resy, released about two weeks out; notoriously hard to book, and game weekends fill fast

Johnny Clark and Beverly Kim's love letter to Ukrainian cooking — modern-meets-traditional, heavy on root vegetables, fermented edges and oily fish, served from a cart of zakusky (appetizers) rolled to your table. Time Out named Avondale the fifth-coolest neighborhood in the world in 2025, the highest-ranked in the United States, and this is the restaurant at the top of it.

Reservations: OpenTable; book well ahead — it's a small, very popular room

One of the Midwest's most serious Edomae counters, run out of a nondescript Logan Square storefront — premium fish flown in from Japan, placed over extra-large grains of aged-red-vinegar rice. It's one of the priciest and most intimate experiences in the city, with the counter often taking a single group for the evening.

Reservations: Tock, released in advance and priced per seating; the counter is tiny, so book the moment a date opens

Gibsons is Chicago steakhouse royalty, and Italia is the group's floor-to-ceiling-glass outpost over the river, where a seafood-forward Italian menu sits alongside the steaks. A power-dining room with one of the best skyline-and-water views in the city.

Reservations: Book online a week or two ahead; request the window side for the river view

The dim, moody basement below Smyth, which holds three Michelin stars and was named the best restaurant in North America on the 2026 50 Best list — the same John and Karen Urie Shields kitchen bringing tasting-menu obsession to a cheeseburger and frites. The ultimate high-low room, and the burger genuinely earns its reputation.

Reservations: Tock; walk-ins welcome at the bar

Old-school River West Italian at its best — a small, loud, autographed-photos-on-the-walls room turning out generous, unfussy red-sauce cooking that locals swear by. It's the anti-scene: no pretense, huge portions, and a tiramisu that regulars call the best in the city.

Reservations: Reservations by phone only — the room is small and books up, so don't count on a walk-in. Closed Mondays

Texas-style barbecue in a warehouse down a brick-paved alley, rock music thumping, meat sold by the pound on butcher paper. Another Sodikoff room (same group as Bavette's), and the one-two punch with High Five Ramen in the basement below is a genuine Chicago experience.

Reservations: Walk-in only — order at the counter, grab a picnic table

Chicago invented tavern-style, and this is the room that rebuilt it: a 14-inch cracker-thin sourdough crust, party-cut into squares, with a charred, spotted underside and sauce that runs edge to edge. It opened on Grand Avenue in 2024 and is small enough that the reservations go in a hurry. The Infatuation scored it 9.1 and named it one of the 25 best pizza places in America; Eater called it Chicago's best new pizzeria of 2025.

Reservations: OpenTable — tables release about a month out and go quickly; walk-ins are realistic right at the 4 PM open if you don't mind a short line

Top Chef winner Joe Flamm's 'Adriatic drinking food' — a warm, buzzy Fulton Market room blending Italian and Croatian cooking, and one of the most consistently praised tables in the neighborhood since it opened. The gnocchi alone draws people back, and the energy makes it feel like a night out, not just a dinner.

Reservations: Book online; weekend evenings fill well ahead on game weekends

Doug Psaltis's modern Greek taverna is one of Logan Square's most reliably excellent rooms — bright, seafood-heavy, mezze built for sharing, with a genuinely deep Greek wine program. The kind of place that works for a big table or a two-top equally well.

Reservations: Book online about a week out most nights; weekend brunch is a scene

Chef Joe Frillman's farm-to-table pasta room is one of Logan Square's marquee tables, built on Midwest produce and handmade noodles. It's the neighborhood's farm-driven cooking at its most polished, and the changing menu means it's never quite the same visit twice.

Reservations: OpenTable, released in advance; weekend evenings book up, so grab a date early

A Bucktown room built on the intersection of Indian and Mexican cooking — a Michelin Bib Gourmand in the 2026 guide and an Esquire Best New Restaurants pick in 2025, with a small, energetic dining room and a chef's-counter tasting menu. One of the hardest tables on the North Side right now, and a cuisine mashup that actually works.

Reservations: OpenTable — new windows released about two months out; set an alert and book early

Beverly Kim and Johnny Clark's reinvention of their Beard-winning Parachute as a Korean-inflected listening bar — vinyl on a proper hi-fi system, a small changing menu, and cocktails as much a focus as the food. The more relaxed sibling to Anelya, a few doors up the same Avondale strip.

Reservations: OpenTable, Wednesday through Sunday from 5 PM; seats are held back for walk-ins too, so a table is realistic either way

The deep-dish that Chicagoans actually argue for — Pequod's pan pizza is defined by its caramelized, almost-burnt cheese ring baked onto the edge of the crust, a texture no other place matches. A Lincoln Park institution, endlessly ranked among the best pizza in America, and the one to try if you only get one deep-dish this trip.

Reservations: Tock; walk-in seating is limited, and the pie takes 30–45 minutes to bake, so book or order early

The farm-to-table pioneer that helped make Logan Square a dining destination, running strong since 1999 — a Michelin Bib Gourmand and the winner of the 2024 James Beard Outstanding Hospitality award. Brunch here is a neighborhood institution, seasonal and produce-driven, and genuinely worth the wait on a slow Sunday morning.

Reservations: OpenTable for dinner; brunch is walk-in only, so arrive early on weekends

Opened in early 2025 by former Chicago Bear Israel Idonije with chef Stephen Gillanders, this South Loop sports bar is one of the closest real Bears-fan rooms to Soldier Field — big screens, high energy, and the owner himself often on the floor on game days. Named for the franchise's roots, when the team played as the Decatur Staleys. The fan-bar pick on this Playbook.

Loud, packed, and jersey-clad on Bears Sundays. High energy, big TVs everywhere, a genuine home-fan crowd. Street parking only. This is where you warm up before the walk to the lakefront.

Reservations: OpenTable for tables; walk-ins welcome, but get there early on game day

A South Loop institution — a rowdy rock club and bar close to Soldier Field, with a rooftop, multiple floors, live music most nights, and a genuinely fun pre-game scene on Bears Sundays. It's part dive, part music venue, all energy, and one of the best rooms near the stadium.

Loud, eclectic, and unpretentious — a rock-club crowd downstairs, a rooftop when the weather's right, and a big pre-game surge on game days. Come for the energy, not for a quiet conversation.

Reservations: Walk-in; ticketed shows are separate — check the calendar

A Printer's Row sports bar with a wide rotating draft list, a wall of TVs, and a laid-back owner-run feel. It's the pre-game anchor for the northern South Loop hotels and one of the better beer selections near the stadium — the go-to before a Soldier Field Sunday if you're basing in Printer's Row.

Friendly, casual, beer-forward. A great room to watch early games before the Bears kick, with attentive service even when it's slammed. Open daily to 2 AM, 3 AM on Saturdays. The neighborhood spot the Printer's Row regulars actually use.

Reservations: Walk-in; larger groups on game day should arrive early

Julia Momosé's Japanese dining bar is the highest-ranked cocktail room in Chicago — No. 11 on North America's 50 Best Bars in 2026, named Best Bar in the Midwest five years running, and honored with the Art of Hospitality award. Precise, seasonal, and quietly astonishing.

Refined and intimate, treating cocktail-making as ceremony. Small footprint, so it fills fast. A grown-up room for a considered drink — book ahead or brace for a wait. Open Wednesday through Sunday from 5:30 PM.

Reservations: SevenRooms — required for the tasting menu and strongly recommended for à la carte; walk-ins are welcome at the bar and in the dining room, first-come, first-served

An elevated-dive on Restaurant Row that punches way above its category — old-Chicago-tavern feel, laid-back but a cocktail menu you'd never expect from a corner bar. It's where you go when you want a great drink on Randolph without the Fulton Market scene, and the kitchen turns out genuinely good late-night food.

A step above a dive — laid-back and unpretentious, with a mix of neighborhood regulars and people out for the night. Surly-in-a-good-way bartenders, solid music, and a great last-stop feel. No line, no attitude, just a good room. Open seven days.

Reservations: No reservations — walk in and grab a seat at the bar

Proof that world-class cocktails don't need to be precious — No. 16 on North America's 50 Best Bars in 2026, poured in a packed, funky room with neighborhood-bar energy and a $6 cheeseburger regulars order without reading the menu. One of Logan Square's anchors.

Loud, eclectic, and busy — funky music, mismatched decor, a crowd that spills in even in winter. High-craft drinks at neighborhood-bar prices and a genuinely fun room. Closed Mondays. Order a burger to go with the cocktails; everyone else is.

Reservations: No reservations — walk-in; it gets packed, so grab a spot early

A big, high-energy River North sports bar that's the best room in the neighborhood for a Saturday of college football — wall-to-wall TVs, every game on, and a staff that will tell you exactly which screen your team is on. The room fills and stays lively all afternoon.

Loud, fun, and packed on game day — a real viewing-party crowd, with music between plays and game sound when it counts. Great for a group posting up for an afternoon of college football the day before the Bears.

Reservations: OpenTable for tables; the phone line is for groups of 6+. Walk-ins welcome otherwise

A 1960s Parisian cocktail bar dropped into the middle of Fulton Market — velvet booths, marble bar, floral wallpaper — and one of only a few standalone cocktail rooms on Restaurant Row. It climbed to No. 30 on North America's 50 Best Bars in 2026, up from No. 39 the year before, and the martini list is among the best in the city.

Romantic and transporting, wonderfully Parisian. You check in with a host and get seated — no hovering for stools. Date-night perfect and quiet enough to actually talk. Expect a short line at peak, since it doesn't take reservations.

Reservations: No reservations — walk-in; arrive before 6 PM on weekends for a velvet booth

A stylish West Loop cocktail bar with serious drinks and zero pretense, and one of the best happy hours in the city — $10 martinis Tuesday through Friday from 5 to 7, served with a batch of the house waffle fries. The neighborhood spot that takes cocktails seriously without being precious about it.

Lively, stylish, and fun — a mix of cocktail drinkers and a later DJ-driven crowd. Grown-up drinks in a room built to actually hang out in. Open Tuesday through Sunday from 5 PM; the kitchen closes at midnight, so order food before then.

Reservations: Walk-in; larger groups and private events can be arranged through their site

Chicago's most legendary tavern, opened by Billy Sianis in 1934 and tucked into the tunnel below Michigan Avenue since 1964 — the widely credited inspiration for the SNL 'cheezborger, cheezborger, no Coke — Pepsi' sketch, and the home of the Billy Goat Curse that trailed the Cubs for 71 years. Newspaper clippings on every wall, grill cooks shouting orders, and history you can taste.

A subterranean dive frozen in time — surreal to find beneath such a polished stretch of the city. Loud, old-school, cash-friendly, and unpretentious. More an experience than a night out, but every visitor should do it once. This lower-Michigan original is the one with the history — the airport and Navy Pier outposts are not the same thing.

Reservations: No reservations — walk up to the counter and order

A River North cocktail-and-dips tavern that landed at No. 27 on North America's 50 Best Bars in 2026 — a retro fit-out and $12 martinis that shouldn't be that good at that price. It shares a building and a bar director with Crying Tiger, another of the city's hot rooms.

Warm, retro, and fun without being fussy — it fills up fast, so the vibe is convivial and a little bit of a scene. Great for a few rounds and snacks before or after a River North dinner. Check out the bathrooms; they're a whole thing.

Reservations: Walk-ins only — no reservations at all, so add your name when you arrive; it fills quickly

A moody, jazz-filled basement cocktail bar beneath The Hoxton from the Boka Restaurant Group — a wide menu organized by spirit and flavor, live music filling the room, and a speakeasy-meets-supper-club feel. One of the most transportive rooms in the neighborhood, and steps from the West Loop hotels.

Underground, dim, jazz-infused elegance — semi-private booths, two bars, a music stage. Dress a notch up and settle in for a multi-drink evening. Note there's a $10 cover Thursday through Saturday from 9 PM on guest-band nights. Ask for a seat near the musicians.

Reservations: OpenTable for booth and table seating; walk-ins welcome at the bar