From our guest guidebooks
This is not a greatest hits list. These are the in-between things. The moments that don’t photograph especially well, don’t come with merch, and somehow end up being the parts people remember.
If you’re in the mood to experience Chicago a little more sideways, start here.
Wrigleyville is not just a neighborhood with a baseball stadium in it. It’s a place with its own internal clock, one that runs on first pitch, last call, and the collective mood of roughly 40,000 people wearing the same color.
If there’s a game during your stay, you’ll feel it. That’s not a warning. It’s part of the charm.
Wrigleyville food and drink is best understood as a spectrum. On one end: deeply specific, slightly uncomfortable neighborhood institutions that should not exist as close to a major sports stadium as they do. On the other: large, predictable places designed to absorb crowds efficiently.
Both have their moments.
This is the platonic ideal of a Wrigleyville bar. Loud, friendly, unapologetically Cubs-obsessed, and exactly what it claims to be. If you want to feel like you are in Wrigleyville, not just near it, start here.
3655 N Sheffield Ave
Historic, enormous, and recently updated without losing its soul. Multiple rooms, big screens, and a sense that generations of people have already had extremely long days here. Worth walking through even if you only stay for one drink.
1059 W Addison St
This is the big bar on Clark and Addison. It’s impossible to miss and impossible to misunderstand. Batting cages upstairs, rooftop space, and—importantly—a dueling piano bar that turns into controlled chaos later at night. It is exactly as ridiculous as it sounds.
3540 N Clark St
An old-school Thai restaurant that feels like it wandered into Wrigleyville from another era and decided to stay. Solid comfort food, late hours, and an interior that includes a slightly mysterious robot connection that no one fully explains but everyone remembers.
3456 N Sheffield Ave
Even if you don’t care about baseball, these are genuinely great. You see the guts of the place, the old details, the strange corridors, and suddenly understand why people get sentimental about it. Game days, you see less than on non-game days, but still worth it.
Indie, Alternative, and Things You Loved at 22 (or Still Do)
One of the city’s most important mid-sized venues. Bands pass through Metro on their way up, on their way back, or on their way to becoming much bigger than the room. The crowd is engaged, the sound is good, and the calendar is consistently strong.
Also, check out the adjacent Smart Bar. Well worth the voyage.
Scattered around Wrigley Field are a handful of bronze statues honoring some of the most important figures in Cubs history. You’ll see Ernie Banks, beloved for both his talent and his optimism. Ron Santo, a fan favorite and longtime presence. Billy Williams, one of the great hitters of his era. And Fergie Jenkins, whose statue sits just outside the park.
The iconic Wrigley Field marquee sign is just as much a pilgrimage point, but here’s the honest advice: if you want a photo, do it on a non-game day. The sign is still there, the sidewalk is calm, and you won’t feel like you’re standing in the middle of a moving river of people. Game days are about momentum. The sign will wait for you another time.
Our nearby pick for coffee and empanadas. Start the day here, or make it an afternoon detour. A very sensible excuse to get out the door.
3612 N Southport
Not a coffee shop in the traditional sense, but absolutely worth stopping in, especially on a cooler day. This Lakeview-Southport location of a UK chocolatier serves rich, velvety drinking chocolate in several styles and flavors alongside confections and pastries. It’s a fun alternative to your usual latte and a nice moment if you’re craving something warm and chocolatey.
3334 N Southport
Warm, refined, and quietly confident. The dining room feels grown-up without being stiff, with good light, good acoustics, and food that rewards paying attention. This is a place for a proper meal that still feels relaxed. (pro tip… gentlemen reading this, surprise your ladyfriend with dinner. She will love it)
1349 W Cornelia
Southern Italian in a fancy neighborhood spot. Wood, compelling booths, excellent service, and a menu that knows exactly what it’s doing.
3335 N Southport
An Argentinian dinner worth making room for. David’s unscientific endorsement: he notices what he takes to be Argentinians dining here and thinks, “Must be good.” Not a census. Just his very personal restaurant research.
3763 N Southport
Thin, bubbly, coal-fired pizza with a little char. An excellent option when dinner should involve pizza but not a deep-dish commitment. We are very much in favor of that distinction.
3707 N Southport
A quick clarification, because this matters.
In Chicago, breakfast and brunch are not the same thing. Breakfast is something you do early and efficiently. Brunch is a social event that starts late, involves waiting, and may quietly derail the rest of your day. Both have their place. Knowing which one you want will save you time and disappointment.
The bagel shop on Southport, and a very good one. Proper bagels, strong coffee, and exactly what you want if you’re trying to get out the door without committing to a full brunch situation.
3737 N Southport
A good nearby choice for weekend brunch, with pancakes, eggs and enough options to let everyone have an opinion.
3455 N Southport
Stephanie Izard’s playful take on the American diner. People love it, and it belongs on the brunch list.
3325 N Southport
If you like movies even a little, the Music Box Theatre is worth your time. Its original auditorium opened in 1929 and still gives a movie the setting it deserves. The screen is huge. The sound is excellent. The building still feels like a place you go on purpose.
They show a mix of first-run films, restorations, repertory screenings, festivals, and things you didn’t know you wanted to see until you saw them listed. The programming is smart and generous, and the audience actually watches the movie. There’s also a live organ, which sounds like a novelty until it isn’t.
If you’re in town for a few days, check what’s playing. Even if you don’t recognize the title, trust the curation. It’s one of those places that reminds you why going to the movies mattered in the first place.
Sit by the window and look into people’s backyards as the train glides past. You’ll see patios, dogs, dinner prep, string lights, half-finished projects. It’s intimate in a way that feels accidental and very Chicago.
Ravenswood is very good at not announcing itself. There are leafy streets, beautiful old apartment buildings, gardens people have clearly thought about, and enough useful things nearby that a perfectly ordinary errand can become a very pleasant afternoon.
Then you reach the railway corridor and the texture changes. Brick industrial buildings, workshops, studios, breweries. This is not a neighborhood that discarded everything interesting about its working life and replaced it with a sign saying “authentic.” People still make things here. Some of those things are conveniently drinkable.
The Brown Line gives the area a rhythm without making the whole place feel hurried. Trains go by. People walk to coffee. Someone has a remarkably good garden. It is a version of Chicago that rewards slowing down enough to notice it.
The Ravenswood branch is on Lawrence at Wolcott, with two floors, a mezzanine, and a patio when the weather permits. A good place for coffee to become breakfast, or for a brief stop to acquire a second chapter.
1831 W Lawrence Ave
A family-owned neighborhood coffee shop at Damen and Leland. Coffee, pastries, breakfast sandwiches, and lunch, without requiring the morning to become a lifestyle announcement.
4700 N Damen Ave
Aaron is particularly fond of this Neapolitan pizza place at Sunnyside and Ravenswood. Properly good pizza, an oven built by artisans from Naples, and very little reason to overcomplicate your order.
1769 W Sunnyside Ave
At Berteau and Ravenswood, another of David’s favorites. Mexican cooking with room for a little wandering: tacos, mole enchiladas, and fillings that go well beyond the obvious. He likes it very much. You may hear about it again.
4217 N Ravenswood Ave
A neighborhood pub on Montrose. David’s verdict: pretty good. Sometimes dinner can be a straightforward affair without anyone demanding that it become a life event.
1834 W Montrose Ave
The Damen location. David loves this place, and the food is delicious. A good reason to head north when breakfast deserves a little more attention.
4747 N Damen Ave
A nearby breakfast and coffee option on Montrose. Useful when you want something close without asking breakfast to change your life.
1812 W Montrose Ave
One of David’s absolute favorite places to go for a tipple. Cocktails, whiskey and gin flights, and light bites in the tasting room, with a patio when Chicago allows it. You do not need to book a tour simply to have a drink.
4241 N Ravenswood Ave
A neighborhood brewery with an unusually literal sense of community: it even has a community-supported growler subscription. Approachable beers and a good starting point for an unhurried afternoon.
1800 W Cuyler Ave
Traditional European brewing methods and a particular affection for lagers. For people who enjoy the idea that a beer can be beautifully made without requiring a paragraph of ingredients involving breakfast cereal.
1800 W Belle Plaine Ave
Lincoln Park is very good at making a perfectly ordinary afternoon feel like something you ought to have planned. There is a lake. There are gardens. There is an actual zoo. You can do quite a lot here without buying a ticket or developing an itinerary with subsections.
Aaron’s favorite for coffee and French-inspired pastries on Webster. A very good reason for a short walk, and a perfectly respectable excuse to call a second pastry breakfast.
1220 W Webster Ave
Not technically coffee, which David considers a point in its favor. The British chocolatier’s Armitage shop serves drinking chocolate alongside its confections. Especially useful when the weather has become personally insulting.
900 W Armitage Ave
A family-owned coffee shop with portraits of actual Chicago shelter dogs dressed as Victorian aristocrats. Finally, a room where the dogs have made an effort. Coffee and a little local character on Clark.
2425 N Clark St
One of David’s neighborhood favorites. Pizza on Webster for the evening when dinner should be easy, generous, and not require a committee.
938 W Webster Ave
Tapas and paella on Halsted. A good answer when everyone wants to try something different and dinner is better shared than negotiated.
2024 N Halsted St
Sonoran-style Mexican food on Webster. Another David favorite, and a useful direction when the evening calls for Mexican food rather than another conversation about pizza.
1200 W Webster Ave
One of David’s favorites. Unpretentious, a bit grungy, delicious, and generous, with the added pleasure of watching the sauce being made at the stove in front of you. Dinner without a thesis statement.
2434 N Clark St
Family-owned Korean street food on Clark: tacos, bibimbap, and kimchi fries. Useful when you want something full of flavor without turning dinner into an evening of formal negotiations.
2568 N Clark St
Seasonal brunch on Webster. A good option when you want a proper plate of food without turning breakfast into a major production. Check the current brunch days before setting out.
1119 W Webster Ave
If you want breakfast to be more of a production, Gemini is the sit-down weekend brunch option. Make a proper occasion of it, and stop pretending this was going to be a quick breakfast.
2075 N Lincoln Ave
Head east for the lakefront, then decide how ambitious you feel. A long walk, a short walk, sitting and looking at the water: all legitimate uses of the place. The skyline does a great deal of the work. On windy days, the lake will remind you that this is not a decorative pond.
Lincoln Park Zoo is free to enter, with no ordinary admission reservation, which remains a rather lovely thing in a city where almost everything else has discovered a service charge. South of the zoo, the Nature Boardwalk gives you a quieter loop around the pond, with city views and room to slow down.
The nearby Lincoln Park Conservatory is the indoor, leafy option. Admission is free, but timed reservations are required, so book before setting off. The Alfred Caldwell Lily Pool is another lovely, quieter stop when open for the season. Check current access rather than expecting every green corner to operate on the same schedule.
Armitage and Halsted are good streets for a proper browse: little shops, clothes, things for the home, and the steady possibility of finding something you suddenly feel has been missing from your life. Clark offers another long run of neighborhood shops and places to stop. You are allowed to look without acquiring anything. In theory.
One of my favorite local activities is watching Lincoln Park mothers pilot $1,200 strollers toward a pastry. These are not conveyances. They are small European vehicles with better suspension than my first car. The women operating them have somehow been to Pilates, answered several consequential emails, and dressed a person who cannot yet hold a spoon, all before I have located my glasses. I admire the competence. I am also a little afraid of it. There is a particular confidence involved in approaching a crowded café with twins, a golden retriever, and the firm expectation that this will all work out. Usually it does. I can barely get myself through a revolving door without a strategy meeting.
This is a neighborhood where people appear to have a preferred baker, a preferred bench, and fairly firm views about both. The scale is friendly. The buildings have character. There are enough ordinary errands happening around you to make visiting feel a little like borrowing someone else’s very pleasant routine.
Just up Lincoln, with Turkish coffee, inventive lattes, and house-made nut milks. For the morning when you would like your coffee to have a little more to say for itself.
4703 N Lincoln Ave
West along Leland, near Rockwell, this independent café and bakery makes a good excuse to explore beyond the square. Coffee, bagels, and a quieter neighborhood morning. Go early; this is not your late-afternoon caffeine rescue.
2601 W Leland Ave
Seasonal American cooking, dishes to share, and a lively room. Useful when the group wants a good dinner without deciding that dinner is now a formal occasion.
4535 N Lincoln Ave
German comfort food on Lawrence. Lincoln Square’s German heritage is still quite capable of feeding you, and this is a sensible place to let it. Arrive hungry rather than merely curious.
2251 W Lawrence Ave
An independent sandwich shop with enough imagination to make “let’s just get a sandwich” a perfectly respectable plan. A good casual counterweight to the evening with the dinner reservation.
4739 N Lincoln Ave
David’s first choice here. House-made pastries and weekend brunch; a good place to settle in rather than eat while trying to locate your other glove.
4729 N Lincoln Ave
A proper neighborhood breakfast: eggs, pancakes, and the reassuring possibility that breakfast need not become an elaborate production.
4357 N Western Ave
Bagels and breakfast sandwiches, very close by. A sensible answer when you want breakfast without scheduling your entire morning around it.
4655 N Lincoln Ave
The Old Town School of Folk Music has concert spaces at 4544 and 4545 N Lincoln. Despite the name, you are in Lincoln Square, not Old Town. Check the calendar: folk, roots, and music from far beyond Chicago all have a home here.
Welles Park, southwest of the square, is where you can sit among people who are simply getting on with their day. Children, dogs, a bit of sport, someone reading. You do not have to turn this into an itinerary.
Logan Square rewards leaving a little room in the day. There are broad green boulevards, side streets lined with old houses, and enough places to stop for coffee or a meal that a short walk can become most of an afternoon. This is not a scheduling failure.
A daytime cafe with coffee and somewhere to settle in. Later it becomes a bar and music venue. This is useful information if your plan was to return for the same quiet afternoon at ten at night.
2313 N Milwaukee Ave
Coffee and pastries on Milwaukee. The cafe is a useful morning stop in its own right, not merely a holding area until dinner begins. Check the current service details if you want to sit down, especially during Sunday brunch.
2375 N Milwaukee Ave
Aaron’s personal favorite. From outside, you would not necessarily predict extraordinary food. That is part of the pleasure. Seasonal cooking with plenty to interest people who would rather eat vegetables than negotiate around them. A very good reason to plan ahead.
2537 N Kedzie Blvd
Tex-Mex on California, with tacos, burritos and margaritas. The straightforward answer when dinner should be cheerful and nobody wants to spend forty minutes deciding how formal they feel.
2101 N California Ave
A small room with ambitious, inventive food, including pastas and dishes that are useful to share. The name does not describe the floor plan. Book ahead rather than assuming a table will materialize because you are hungry.
3209 W Armitage Ave
A contemporary Chicago inn with seasonal food and a serious interest in whiskey. A good choice when you want a proper dinner and would be perfectly happy if the evening continued at the bar.
2657 N Kedzie Ave
Biscuits, pie and a counter-service approach to the morning. Order first, then find a seat. If a slice of pie somehow joins breakfast, we are not the people who are going to intervene.
2051 N California Ave
The Logan Square Boulevards Historic District gives the neighborhood much of its shape. Walk along Kedzie or Logan Boulevard and look up occasionally: limestone houses, older apartment buildings, porches, masonry and the sorts of details people once bothered to put over a window.
At the square, the Illinois Centennial Monument is the tall column topped by an eagle. It is a useful landmark even if you have not developed a sudden interest in monumental columns.
For a quieter green interlude, head to Palmer Square. There is a path around the park, mature trees and room to sit. Younger children may appreciate the Velveteen Rabbit-inspired play area; adults are allowed to appreciate a bench.
City Lit Books is at 2523 N Kedzie Blvd, next to Lula. Go in before or after a meal and have a browse. They host author events and book clubs too, so check the calendar if that sounds like your sort of evening.
For a longer walk, the Bloomingdale Trail runs along a former elevated rail line. It is part of The 606, with access from California Avenue at Bloomingdale. You can walk east toward Bucktown and Wicker Park or west through the neighborhood. It is a shared trail, so leave room for people moving faster than a leisurely visitor.
The raised viewpoint is part of the attraction. You are looking across gardens, streets and the backs of buildings rather than collecting another view of the skyline. Turn around whenever you like. There is no prize for making the walk more ambitious than you intended.
If a market is on during your stay, it is a very good way to lose part of a morning to bread, produce and something you meant to eat later. The outdoor Logan Square Farmers Market is seasonal; winter arrangements have different days and a different location. Check the current calendar before setting out.
The downtown is a lovely walk in general.