Cindy'sChicago

My favorite thing to do when people visit. You see the whole city from the water and it never gets old.

We don't claim "Willis." Go to the Skydeck, and only on a sunny day — the whole point is the view. The photo experience is on the lower level.

If you skip Sears, get a cocktail up here instead. Same city, fewer crowds most of the time.

Good food and drinks. In summer there are DJs and live music.

Where you'll find the Bean. Go early for the shot.

All summer there are free concerts and movie nights at the pavilion — check the schedule before you plan a night out.

This is the skyline shot everyone has seen and nobody can name. Walk past the building to the lakefront path.

An old quarry turned into a park. Climb to the top of the hill and the city is right there.

River in front, skyline behind. Pair it with lunch in Chinatown Square.

Worth the trip south. Locals swim off the rocks in summer.

An elevated trail on an old rail line, running through Humboldt Park, Logan Square, and Wicker Park. Walk it, don't drive between those neighborhoods.

Free, and better at night than in daylight.

Free, always. One of the largest Mexican art collections in the country and it sits right in the neighborhood. Start here.

Free. The Tiffany dome is better than the Bean and there's never a line.

Free. Six acres of glass houses. Go in winter when you need it most.

Free, always, right in the middle of the city.

Small, and worth building an afternoon in Humboldt Park around.

If you only do one paid museum, do this one.

All three sit together on the lakefront. Pick one — doing all three in a day is how you end up hating museums.

Enormous. Best with kids, or if you're the kind of adult who still likes the submarine.

The oldest independent Black history museum in the country.

18th Street — murals, panaderías, taquerías, shops. Walk it slowly. This is the one I'd send you to first.

26th Street, under the arch. One of the busiest shopping strips in the city and almost no visitors ever make it here.

The steel flags over Division are beautiful in person. Paseo Boricua between them is the heart of it.

My favorite neighborhood for dinner. Randolph Street is packed with restaurants and it's easy to walk from one to the next.

Chinatown Square is full of shops and restaurants. Ping Tom Park is a block away.

Bars within stumbling distance of each other and a must if you like baseball. Young, college crowd — know what you're walking into.

Where to go if you want to shop, eat, and not be around tourists.

Soldier Field, where the Bears play.

Stuffed deep dish on the Southwest Side, family-run since 1992. Adrian Zamudio took it over when he was eighteen and you'll usually find him at the counter while the rest of the family works the kitchen. Dough made fresh daily, cheese ground fresh daily.

There are other Angelo's in Chicago. You want 4850 S. Pulaski.

The caramelized cheese crust is the whole thing. Most Chicagoans will tell you deep dish is for tourists — but you're a tourist, so go.

My favorite steakhouse in the city. Latin flavors, serious steak. Named after chef Stephen Sandoval's grandfather.

Go downstairs afterward to Laberinto, the speakeasy.

Carlos Gaytán came to Chicago as an undocumented immigrant and started as a dishwasher. He became the first Mexican-born chef to earn a Michelin star. The restaurant is named after Huitzuco, his hometown, and the top seller is his mother's cochinita pibil.

Pepe Barajas is self-taught. He came from Mexico City at seven, started washing dishes at twelve at his family's taquería in Little Village, and named this place after his aunt Josefina, who raised him like a second mother. Three agave bars, including one on the roof.

That family taquería is Los Comales on 26th Street — also on this list.

Opened by the son of the Nuevo León family after the original burned down. Mesquite-grilled arrachera and the best flour tortillas you'll have here.

Peruvian, from Lima chef Gastón Acurio's group, with a Lima-born chef running the kitchen. Order the ceviche and a pisco sour.

Peruvian-inspired, on the roof of The Hoxton. Lobby bar before, speakeasy after.

Mexico City-inspired, heirloom corn nixtamalized in house. Deep tequila and mezcal list.

Mediterranean, and one of my favorite rooms in the city. Come for the space as much as the food.

Steak that's actually affordable.

Omakase, timed seating. Reserve ahead.

Brazilian, huge and colorful, and they run a Latin-Brazilian floor show plus a cabaret speakeasy tucked off to the side. Check what's on before you book.

Colombian steakhouse and live music venue in the same room. Bandeja paisa, empanadas, chicharrón con yuca frita. Bands play and the floor turns into a dance floor. Open late on weekends.

Middle Eastern, and the room is the reason to go — the owner brought artifacts back from trips through the Middle East and North Africa and brought in craftsmen from Syria, Egypt, Morocco, and Lebanon to build it. Belly dancing, live singers, and rotating special events.

Al pastor is the order. The Pilsen location on Blue Island runs until three or four in the morning on weekends, which makes it the late-night one.

Carne en su jugo. Same block for over thirty-five years.

Gorditas at the butcher counter. Ask for handmade tortillas.

Al pastor with pineapple, no frills, cash discount.

A Little Village institution — and the family restaurant where the chef behind La Josie started washing dishes at twelve.

They chop it to order in front of you and hand you a sample while you wait. Get the corundas too.

Opens at five in the morning on weekends. That's the move after a late night.

Small, always a wait, worth it. Discount if you pay cash.

Goat birria, handmade tortillas, counter seating only.

Smash burger on plantain buns. Small space, quick service.

Rotisserie chicken jibarito with arroz con gandules. Right across from Smash, so you can do both. Closed Sundays.

Puerto Rican, and the jibarito people drive across the city for. Get the alcapurrias and the tostones too. They do coffee as well — the coquito latte is the order.

The easiest one if you're staying downtown.

Dominican home cooking, cheap and generous. Oxtail, coconut codfish, fried redfish, bistec with tostones. Closed Mondays.

Sunday nights are karaoke, and they stay open late for it.

The Maxwell Street Polish was invented here. Jimmy Stefanovic fled Macedonia, waited years for a visa, and took over his aunt's hot dog stand in 1939. His grandson runs it now — three generations.

Go to the one below Michigan Avenue — that's the original, the one that was the unofficial clubhouse for the city's newspaper reporters. Ask for fries and you'll get the line: cheeps, no fries; Coke, no Pepsi. Sam Sianis, who ran it for five decades and was the man Belushi was doing on SNL, died in 2026. His sons run it now.

Pizza on the water.

Post up with a cafecito or a cocktail and people-watch on the Riverwalk.

Run by a husband and wife who still sell paletas off the bikes around the neighborhood. This is the one.

The owner takes your order herself. Mangonadas, fruit with chamoy, tamales, aguas frescas.

Tiny, barely reviewed, and the best conchas on 18th Street. Grab a tray and tongs.

The institution. Pan dulce, empanadas, tortillas, and vegan conchas if you need them.

Jalapeño cream cheese bread. Closes mid-afternoon, so go early.

Coconut tres leches and a horchata latte, from the couple who own it. Closed Mondays.

Guava tres leches. Recently reopened and bigger than before.

Coffee shop by morning, cocktail lounge by night. Owned by Carolina Gonzalez and Josean Irizarry — Mexican and Puerto Rican — with local artists' work rotating on the walls monthly.

Carolina built the bar program at Trino, including Laberinto downstairs — so if you liked the drinks there, you know why you like them here.

Sachayra Cintron brings her beans straight from Maricao, Puerto Rico. Quesitos, bizcocho mojadito, and coffee that tastes like it came off the island because it did.

Wanda opened it in 2002 as a tribute to her grandmother, whose house always smelled like fresh coffee. Handmade Puerto Rican pastries and bread.

Coffee plus a small market of Puerto Rican art and jewelry, with most of the proceeds going back to the island.

Cuban coffee and Cuban sandwiches, made to order.

Mexican-American brunch on 18th Street. The name reclaims "pocho" — a word used against people of Mexican descent who don't speak perfect Spanish. The owners describe it as not really Mexican, not really American, somewhere in between. Get the chilaquiles.

Guatemalan and Mexican. Guatemalan breakfast, chilaquiles verde with birria, enfrijoladas, and a banana syrup oat latte. They serve dinner later in the week too, so it's not only a morning place. Closed Tuesday and Wednesday.

Opened by Marlene Torres, a DACA recipient who went back to school at 28 and beat cancer to open it. She died in 2022 and her husband sold the shop rather than close it — it's now run by a husband and wife from Mexico City. Café de olla, chilaquiles, crepes.

My favorite rooftop in the city — the lake, the skyline, and the zoo all at once. There's a retractable roof, so it works year-round, not just in summer. Family-friendly early, 21+ from 8pm on the back half of the week, and there are DJs on weekends.

Beautiful room in a converted bank. Cocktails are the point, and they bring in live music and DJs on some nights.

The Dawson is a few blocks away — easy to make a night of the two.

Hidden behind Moreno's Liquors, the family store that's been on 26th Street for over forty years. Third-generation Mike Moreno opened it — the first new bar in the neighborhood in decades — and named it after the family chihuahua. Look for the red neon dog. Enormous agave list.

Prohibition-era supper club across three floors with one of the largest American whiskey collections anywhere. The entertainment is the point — live jazz, DJs, and a burlesque revue. 21+, closed early in the week, open until 3am on Saturdays.

A working barbershop in front, a bar hidden behind it. Usually a line, so book a table and walk straight through.

Wood-fired food, a big two-level room, and one of the better patios downtown.

The boat-shaped place right on the sand — now reopened as a beach club with dining decks and cabanas you can rent. There's a 21+ section and a family-friendly restaurant side. Summer only.

The easiest one if you're staying downtown — dinner and live sets in the same room, around a $20 cover. Reserve, and show up at your reservation time or you'll wait outside.

Open since 1907 and it feels like it. During Prohibition it ran as a speakeasy and Al Capone drank here — his booth is still there, positioned so he could watch both doors, and the tunnels they used to move liquor are still under the building. Live music every night. It's also where the first poetry slam in the world started, in 1986, and it still runs weekly.

Covers run about $15–20. Get there early or you're standing.

A listening room, not a bar — people come for the music and they're quiet during sets. No food, so eat first. Reserve for a good seat.

Buddy Guy still turns up and plays. Cajun and soul food, and the walls are covered in guitars and history. Closed early in the week.

Two stages running alternating sets so the music never stops. Open until 4am on weekends.

Small, no food, Blues Hall of Fame regulars on stage. Be there by nine if you want a seat.

The big room. Only open for shows, so check the calendar rather than dropping in.

Second City is the famous one and worth doing once. Laugh Factory and Zanies are cheaper, smaller, and often funnier.

A restored 1892 opera house on 18th Street. The most beautiful venue in the city and it's in the neighborhood you already want to be in.

Sat empty for decades and the neighborhood fought to bring it back. Now it's open again for shows.

Salt Shed, Metro, the Aragon, and the Chicago Theatre, depending on who's in town.

There's a social somewhere in this city almost every night of the week. Ask at any of the Latin spots on this list and someone will tell you where to go.

Wrigley for the Cubs, Rate Field for the Sox, the United Center for the Bulls and Blackhawks. If you're at the United Center, drive past the Michael Jordan statue.

Touring productions in the Loop's old theaters. Worth it for the rooms alone.

Exactly what it sounds like, plus a full music lineup.

Worth building a weekend around.

Two of the biggest neighborhood festivals in the city, both on 18th Street.

Division Street shuts down. If you want to understand Paseo Boricua, come for this.

Parades in Pilsen and Little Village and caravans downtown. Loud, packed, and the best weekend of the year.

Both free. See the jazz and blues section — this is the same story outdoors.

The big ticketed ones. Book everything far ahead if you're coming for either.

Neighborhood street fests worth wandering into.

Touristy and I don't care. Get the glühwein and keep the boot.

Oak Street for downtown and the skyline behind you, North Avenue for volleyball and crowds, Montrose if you want space and quiet.

Eighteen miles along the water. Rent a bike and ride even a piece of it.

Free, like the zoo itself. Worth the frozen hands.

A ribbon that winds through the park instead of a rink. Better than the one at Millennium.

Free, warm, and full of things that are alive in February.

Download the Ventra app or just tap your phone at the turnstile. The Red and Blue lines run 24 hours. Both airports connect straight downtown — Blue Line from O'Hare, Orange from Midway.

Parking downtown is painful and expensive. If you have to drive, book a spot on SpotHero ahead of time instead of circling.

Runs along the river in the warm months and it's the best-value view in the city. Cheaper than a boat tour and it actually gets you somewhere.

Docks everywhere. Best way to do the Lakefront Trail or the 606 without committing to a rental.

State and Madison is zero. Every address counts out from there, and 800 numbers equal a mile. Once you know that you can find anything without your phone.

A lot of the best spots on this list don't take cards — the Green Mill, Blue Chicago, Atotonilco, Cantón Regio, Los Gallos, and every street vendor. Some places give you a discount for it.

Eighteen to twenty percent at restaurants and bars, a dollar or two a drink at a counter, and cash for the carts.

May through October if you want the city at full volume. Come in winter and you'll get the museums, the music, and no lines anywhere.