Dimo’s Wrigleyville

Creative pizza by the slice · lower cost casual meal. 3463 N Clark St. Locations · Menu

The macaroni and cheese pizza is David’s absolute favorite.

Vegan pizzas are available. Slice choices vary by day.

Coda di Volpe

Southern Italian pasta and Neapolitan pizza · nicer neighborhood dinner. 3335 N Southport Ave. Official site · Menus · Reservations

A good choice for a nicer evening meal.

Reservations are available through the official booking link.

Ella Elli

Seasonal small plates with Mediterranean influences · nicer date night. 1349 W Cornelia Ave. Official site · Menus

A good choice for a special occasion dinner.

Reservations through Tock. A 3.5% administrative fee is added; it is not a tip.

Tango Sur

Argentine steakhouse and grilled meat · sit down steak dinner. 3763 N Southport Ave. Official site

Reservations by phone only: 773 477 5466.

Steingold’s Deli Southport

Jewish deli and bagels · quick casual breakfast or lunch. 3737 N Southport Ave. Official site · Southport ordering

Takeout is available. This link is for the Southport location.

Coalfire Southport

Coal oven pizza · casual dinner. 3707 N Southport Ave. Official site · Southport menu

Vegan and children’s pizzas are available. Usually closed Mondays.

Little Goat Diner

Creative American diner · casual brunch or dinner. 3325 N Southport Ave. Official site · Menu

Children’s and vegan menus are available. Check current booking options.

Diner Grill

American counter diner · inexpensive breakfast and late night meal. 1635 W Irving Park Rd. Official site

One of David’s favorites: a small, simple diner with the grill close to the seats.

Open 24 hours. No reservations. Seating is mainly at the counter.

Chicago Diner — Lakeview

Vegan and vegetarian comfort food · casual diner. 3411 N Halsted St. Official site and location

A destination for many vegetarian and vegan visitors. A longtime meat-free Chicago diner serving comfort food, including the Radical Reuben, seitan wings and shakes.

The menu also offers dairy cheese and eggs. Choose the vegan preparation where alternatives are offered.

The Pasta Bowl Lincoln Park

Italian American pasta · casual dinner with large portions. 2434 N Clark St. Official site · Locations

One of David’s favorites for simple, delicious pasta. You can watch the sauce being made at the stove.

Ask the restaurant about food allergies or menu changes.

Armitage Alehouse

British-style pub food and Indian-inspired dishes · nicer occasion dinner. 1000 W Armitage Ave. About · Menus

An elegant British-style setting with delicious food. David especially recommends the pot pies.

Reservations open 21 days ahead at 9 am. The bar serves the full menu and accepts walk-ins.

Spacca Napoli

Neapolitan pizza · moderate neighborhood dinner. 1769 W Sunnyside Ave. Official site · Menu

One of David’s favorite places for Neapolitan pizza.

Call 773 878 2420 for reservations. The gluten-free dough contains wheat starch; the kitchen cannot guarantee a gluten-free environment.

The Warbler

Contemporary American comfort food with pasta and flatbreads · moderately priced family dinner. 4535 N Lincoln Ave. Official site

Reservations through Resy for groups of up to six.

Himmel’s

German and Italian comfort food · moderate dinner. 2251 W Lawrence Ave. Official site · Menu

Reservations by phone, email or text through the website. Children’s menu available. Usually closed Mondays and Tuesdays.

Jerry’s Sandwiches

Inventive sandwiches · casual lunch or dinner. 4739 N Lincoln Ave. Official contact page · Current ordering

The ordering page uses the name Jerry & Geraldine’s. Closed Thanksgiving, Christmas Eve and Christmas Day.

Vaca’s Creamery — Lincoln Square

All-vegan ice cream · ice-cream stop. 2324 W Giddings St. Locations · About the ice cream

A fully vegan ice-cream stop in Lincoln Square, with seating.

Falafel & Grill Montrose

Middle Eastern and Mediterranean wraps and plates · lower cost casual meal. 1433 W Montrose Ave at Clark. Locations · Official site

A David favorite for the food, despite the plain storefront and bright blue lighting.

Dine in, pickup or delivery. Falafel and hummus are marked vegan.

Kale My Name

100% plant-based food · casual vegan meal. 3300 W Montrose Ave. Official site

A vegan neighborhood restaurant on the Montrose corridor.

Lula Cafe

Seasonal American food with many vegetable dishes · moderate brunch or nicer dinner. 2537 N Kedzie Blvd. Menus · FAQ

Aaron’s personal favorite. The simple exterior does not suggest how good the food is.

No daytime reservations; dinner reservations are available. Step-free entry and accessible bathrooms. A 20% service charge is added.

Bang Bang Pie & Biscuits

Pie, biscuits and daytime meals · casual bakery stop. 2051 N California Ave. About · Menu

Order at the counter, then find a seat. No reservations. Usually closed Mondays and Tuesdays.

Lonesome Rose

Tex Mex tacos and burritos · casual neighborhood meal. Logan Square: 2101 N California Ave. Andersonville: 5310 N Clark St. Official site · Menu

Reservations through each location’s Resy link. Vegetarian fillings are available.

Daisies

Italian and Midwestern pasta with bakery and lunch service · nicer dinner. 2375 N Milwaukee Ave. Official site · Menus

Reservations through OpenTable. A 25% service charge is added; an extra tip is not expected. Discuss gluten-free requests in advance; substitutions take about an hour.

Giant

Contemporary American small plates and pasta · higher-priced dinner in a small room. 3209 W Armitage Ave. Official site

A small dining room with 45 seats; book early. A 5% health-insurance surcharge is added.

Longman & Eagle

Seasonal regional American food with a whiskey bar and inn · brunch and dinner at a range of prices. 2657 N Kedzie Ave. Dining · Official site

Limited dinner reservations are available. Patio, bar and brunch seating are walk-in only.

Bungalow by Middle Brow

Sourdough pizza, bread and pastries · casual pizza. 2840 W Armitage Ave. Official site

Madison’s pick for sourdough pizza, house-made bread and pastries, beer and natural wine.

There is a covered patio; check the current outdoor setup in cold weather.

Parson’s Chicken & Fish — Logan Square

Chicken and fish · casual neighborhood meal. 2952 W Armitage Ave. Official site · Patio information

Madison recommends this casual chicken-and-fish spot and its patio.

Off-season patio use is weather-dependent, with to-go orders from the bar rather than full outdoor table service.

Table, Donkey and Stick

Alpine-inspired seasonal cooking · sit-down dinner. 2728 W Armitage Ave. Official site · About

One of Madison’s neighborhood recommendations for house-made bread and charcuterie, artisan cheeses and wine.

Jeni’s Splendid Ice Creams — Logan Square

Ice cream · dessert stop. 2512 N Milwaukee Ave. Chicago scoop shops

Madison’s ice-cream pick has locations beyond Chicago; this Logan Square scoop shop is the local stop to keep in mind while exploring Milwaukee Avenue.

m.henry

American and international breakfast, brunch and lunch · moderate daytime meal. 5707 N Clark St. Official site

David’s breakfast favorite and worth the trip to Andersonville.

No reservations; weekend waits can be long. Vegan tofu and gluten-free bread are available. Ask about food allergies.

Lost Larson

Scandinavian and French-style pastries, bread and coffee · casual daytime stop. Andersonville: 5318 N Clark St. Wicker Park: 2140 W Division St. Official site

A daytime bakery and coffee stop, not a dinner restaurant. Online ordering is available.

Schwa

Contemporary American tasting menu · expensive special occasion dinner. 1466 N Ashland Ave. Official site · Booking

Creative dishes served by the chefs, with loud music and a relaxed atmosphere.

Reservations required. Bring your own drinks. Get dietary approval by email before booking, then submit requirements through OpenTable by Tuesday of the reservation week.

Avec West Loop

Mediterranean shared plates · higher-priced dinner. 615 W Randolph St. West Loop location · Menus

A David favorite. Warm, wood-paneled room with shared tables and dishes for sharing.

Reservations are available. This is the original West Loop location.

Maple & Ash

Wood fired steakhouse and seafood · expensive celebration dinner. 8 W Maple St. Chicago location

A dramatic dining room for a celebration.

Book ahead and check the dress code.

Pizzeria Uno

Chicago deep dish pizza · casual sit-down meal. 29 E Ohio St. Official site and menu

The original Pizzeria Uno location. Reservations and online ordering are available through the website.

Lou Malnati’s — River North

Chicago deep dish pizza · casual sit-down meal. 439 N Wells St. Official location, menu and reservations

A Chicago deep dish pizza classic. This River North location offers dine-in, pickup and delivery. Other locations are listed on the website.

RPM Steak

Modern steakhouse · expensive dinner. 66 W Kinzie St. Official site

A polished, modern steakhouse.

Book ahead. Check the menu for current steak prices.

The Drifter

Cocktails and small bites · River North. 676–8 N Orleans St, in the basement under the Green Door Tavern. Official FAQ

One of David’s favorite bars to recommend: cool and worth finding.

Age 21 and over. No reservations; weekend waits are possible. Not wheelchair accessible or suitable for people who need a celiac-safe kitchen.

Green Mill

Jazz bar · Uptown. 4802 N Broadway. Official FAQ

A jazz bar with a 1920s feel.

Age 21 and over. Cash only. No food or reservations. Entry price depends on the show.

Blind Wolf

Hidden basement bar · Lakeview. 3222 N Sheffield Ave, formerly Room13. Official information

Age 21 and over. No food. Walk-in seating only. Usually no entry fee, except for special events. Smart casual dress.