Chicago

The Reliance Building

Root/Atwood, 1890/1895

A then-unprecedented amount of glass was used in this early skyscraper, bewildering a public still used to masonry walls. Note the difference between the first two floors and the ones above: hold-outs among the previous building's tenants forced developers to build the foundation and the first two floors under the top three floors from the old building, and then knock off the top three when their leases had expired. It was restored when it became the Hotel Burnham (see below) in 1999, and can be explored with a stop at the Atwood Cafe (also below).

Monadnock Building

Burnham & Root, 1891

Named appropriately for a mountain in New Hampshire, the Monadnock was the last tall building to be supported by its own walls (not a metal frame, although the 1893 addition by Holabird & Roche does use one). It's a masterpiece of simplicity and power in form. The block-long hallway that serves as a lobby has incredible ambiance: it's always kept at a level of brightness that suggests gas lamps, and the small stores on the first floor (a coffee shop, a shoe-shine, a restaurant) are all turn-of-the-century tile-and-polish.

Heritage listed

Sunset Cafe

Ace Meyers Hardware Store

Countless jazz legends played at this legendary jazz club, including: Bix Beiderbecke, Jimmy Dorsey, Benny Goodman, Earl Hines, Fletcher Henderson, Count Basie, and of course, Louis Armstrong. The club was run by unsavory mafia types and the musicians often had no choice but to keep playing here! Disjointed as it may be, the legendary club no longer exists and the building houses a hardware store. Nonetheless, the Sunset Cafe is Chicago's number one jazz history site and should not be missed by anyone traveling along The Jazz Track. There has been talk of resurrecting the club, but plans remain embryonic. Feel free to stop in if you'd like — the owner is used to all sorts of foreign jazz aficionados wandering in.

Mon-Sat 9AM-6PM, Sun 11AM-2PM

Alliance Bakery & Café

Just a look at the whirls of frosting and gingerbread fortresses in the window tends to bring a smile. The tarts, cupcakes, and coffee back that up. Alliance has been here for more than 80 years. There's a pleasant, inviting cafe next door with free WiFi.

Mon-Sat 6AM-9PM, Sun 7AM-9PM·$3-7 · Wheelchair accessible

Gio's Cafe & Deli

Some of Chicago's best Italian is hidden in a tiny checkerboard tablecloth deli, more resembling a grocery store than a restaurant, hidden further still in the residential streets of Bridgeport. It's also, as you might expect, a steal of a bargain. Delicious Italian pastas, chicken, and panini.

Mon-Sat 8AM-9PM·$5-25 · Vegetarian options

Chopin Theatre

An experimental theater complex encompassing two stages, a cafe, and a gallery. Many works in translation from Eastern Europe have made their US debut here, although the theater keeps strong ties to Wicker Park and local history as well.

$12-22

3rd Coast Cafe

Once known as the Chicago meet-up spot for 2600, the computer hackers quarterly, 3rd Coast is an upscale late-night oasis amid blocks of impressive, silent Old Town row houses. Evenings feature jazz and solo guitarists, and the food is far above average for a cafe.

7AM-midnight daily

Cafe Jumping Bean

Reputation has it that this is Chicago's warmest and most inviting neighborhood coffee shop. It certainly lives up to the name: tiny, and always jumping with people.

Mon-Fri 6AM-10PM, Sat,Sun 7AM-7PM·$2-6

Coco Pazzo

Very tasty Italian cafe. Try the gnocchi, and save some room for the fruit desserts.

Lunch Mon-Fri 11:30AM-2:30PM; dinner Mon-Thu 5:30-10:30PM, Fri Sat 5:30-10:30PM, Sun 5-10PM·$30+

Kristoffer's Cafe and Bakery

A warm, large space with a range of sandwiches, drinks, and baked goods. (They call their seven varieties of tres leches cakes a family specialty.) You will find free Wi-Fi and flyers for every art opening in the area.

Mon 7:30AM-3PM, Tue-Fri 7:30AM-5PM, Sat Sun 8AM-4PM·Lunch $5-8

Letizia's Natural Bakery

Breakfast sandwiches, espresso and baked goods with good, healthy cooking. If you enjoy Letizia's, come back later for Enoteca, the wine bar under the same management next door.

6AM-11PM daily·$4-12

Panaderia Tortilleria Nuevo Leon Bakery

Tasty bakery run by the Nuevo León family, who run the fine restaurant a block down. They serve Mexican bread, pastries, coffee, and other early morning essentials under the watchful eye of a 1986-87 Chicago Bears team poster.

Mon-Fri 5:30AM-9PM, Sat Sun 6AM-9PM·$1-4

Uncommon Ground

It's almost unbelievable that such a lovely, relaxed bar/cafe is this close to Wrigley, but there it is. Evenings see a full schedule of acoustic music with a full bar of beer, cocktails, and wine, while organic breakfast, lunch and dinner are served all day, and two fireplaces await in the winter. Uncommon Ground also hosts the annual Jeff Buckley Festival, now in its tenth year, in honor of the singer's legendary 1994 performance there.

Sun-Thu 9AM-11PM, Fri Sat 9AM-midnight

Roscoe's

Roscoe's is a multi-purpose bar — by night, there are good drink specials and a great dance floor, but by day, you'll find a relaxed neighborhood bar with artwork by local artists and a sidewalk cafe (in the summer) for lunch.

Mon-Thu 3PM-2AM, Fri 2PM-2AM, Sat 1PM-3AM, Sun 1PM-2AM

Siam Noodle and Rice

Excellent family-owned homestyle Thai cafe; an Uptown favorite.

Tue-Thu 11AM-9PM, Fri 11AM-9:30PM, Sat 11:30AM-9:30PM, Sun 11:30AM-8PM, Mon closed·$6-9

The Wormhole

With a prop DeLorean in the front window, this quirky 80s themed coffee shop offers up local baked goods and fresh coffee. Ample seating, if you get there at the right time. Offers WiFi and a TV set up with vintage video games.

7AM-9PM daily·$3-12 · Wheelchair accessible

Bridgeport Coffeehouse

Starbucks doesn't exist in Bridgeport and in this coffeehouse, the staff knows their customers by name. Features original blends roasted in house and some excellent loose-leaf teas. Free wireless, live jazz on Sundays, and live blues on Wednesdays.

Mon-Fri 6AM-9PM, Sat 7AM-9PM, Sun 8AM-7PM

Illy

Illycaffè S.p.A. (branded and stylised as illy) is an Italian coffee company specializing in espresso, headquartered in Trieste. Illy markets its coffee globally in silver and red pressurized, oxygen-free cans; operates a network of cafes on shopping streets, in museums, and in airports; and, since 2009, has marketed a line of coffee-flavoured energy drinks as illy issimo. Either as whole beans or ground coffee, Illy offers medium, dark, and decaffeinated roast variations, as well as single-origin arabica variations, as available, each from Brazil, Guatemala, Ethiopia, Colombia, Costa Rica, Nicaragua, Tanzania, or India.

Cafe Hoang

It's at the far end of the block, but Cafe Hoang is worth the walk. The menu features several pages of Vietnamese options and a page of Thai. The portions are generous, the food is flavorful, and it's hard to resist spending a while. They make a mean durian smoothie.

Mon Wed-Thu 11AM-10PM, Fri Sat noon-10:30PM, Sun noon-10PM, Tue closed·$8-12

Kopi

Describes itself as "a traveler's cafe." In practice, it's a relaxed coffee shop of the early 1990s vintage, with earthy decor and earnest staff. Also includes a small shop of eclectic things from around the world.

Mon-Thu 8AM-11PM, Fri 8AM-midnight, Sat 9AM-midnight, Sun 10AM-11PM

Plymouth Restaurant & Bar

The Plymouth Restaurant is merely an adequate cafe serving diner-style food, but come here instead for the rooftop bar. Sipping a cocktail while gazing off the balcony at the Harold Washington Library and various Louis Sullivan masterpieces is a fine way to cap off a day of sightseeing, provided that the blaring music doesn't drive you away.

Sun-Thu 11AM-11PM, Fri Sat 11AM-midnight

Sitdown Cafe

Italian cafe/sushi bar serving up eclectic menu of fresh sushi, sandwiches, soups, and salads. Standout dishes include, oddly enough, their thin crust pizzas ($7 plain!), edamame (boiled peas on the pod done right), and a few favorite rolls like Chicago Fire and crunchy crab. Loft-casual decor with outdoor seating and full bar.

Sun-Thu 11AM-9:30PM, Fri Sat 11AM-10:30PM·$8-25

Thai Pastry

Inside the Tai Nam Market Center, this is a Thai bakery with a nice sit-down area to relax over coffee, although they do have a full lunch and dinner menu.

Sun-Thu 11AM-10PM, Fri Sat 11AM-11PM·$8-10 (meal)

Chicago Arts District

This information center is located in the midst of things at 18th and Halsted, but it is generally only open to coincide with the 2nd Fridays Art Walk, so a stop to gather event cards at Kristoffer's Cafe (see Cafes) will be more informative on other days.

Salonica

Adequate, but overpriced, diner fare with some Greek and Mexican entries, and a constant flow of coffee. The nice atmosphere and comfy booths are the real reason to come and lounge about.

7AM-10PM daily·$7-14

Artopolis Bakery & Cafe

Greek artisan breads provide the foundation for bakery treats, sandwiches, and wood-fired pizzas. There's a full bar and wine list as well.

Cafe Mon-Thu 9AM-midnight, Fri Sat 9AM-1AM, Sun 10AM-11PM; Kitchen Sun-Thu 11AM-11PM, Fri Sat 11AM-midnight·$8-16

Lula Cafe

A very popular neighborhood restaurant, serving an eclectic mix of new inventions and creatively remixed standards. Because of its popularity, lines can be really long on Friday and Saturday nights.

Sun Mon Wed Thu 9AM-midnight, Fri Sat 9AM-1AM, Tue closed·$16-30; Monday Night Farm Dinner $24 per person

Meli Cafe & Juice Bar

A bright and relaxed brunch option, with cage-free eggs and Mediterranean-influenced soups and sandwiches.

Mon-Sat 6AM-4PM·$9

Polo Cafe & Catering Bridgeport USA

A fine Bridgeport steakhouse decked with Mayor Daley-worship decor. Show up early on Saturday for the "Bloody Mary Brunch" and try "The Mayor's Steak and Eggs."

lunch: Mon-Fri 11AM-3PM, dinner: Wed 6PM-8PM, Fri Sat 5PM-9PM, brunch: Sat 9AM-2PM·$15-40

Reva and David Logan Center for the Arts

Logan Center

This stunning new building brings professional, student, and community performing arts activities, creative arts studios, digital media production and gallery space under a single roof. The Logan Cafe offers a small plates menu, plus coffee, wine, and beer.

Mon-Sat 8AM-10PM, Sun 11AM-9PM. Performance hours vary·Ticket prices vary by show