Chicago/Lakeview-North Center

For many years, Lakeview was so far away from the action that opening a saloon on Clark Street was a considered a peaceful retirement for convicted ex-politicians in Chicago. With the expansion of the elevated train system, however, that changed rapidly, and with the 1914 construction of Weeghman Park, later to be known as Wrigley Field, Lakeview became the capital of the North Side. The Chicago Cubs, also known as the most dominant baseball franchise of the 19th century, took up residence at Wrigley and commenced the hundred-year lack of success that made them famous. Other teams have slumps, but the Cubs were beyond compare, tormenting their fans with a hundred years of near-misses, late collapses, and abject futility that is unrivaled in American professional sports. The curse finally came to an end, though: in 2016 they won their first championship in over a century. But win or lose, Game Day is always a joy in Wrigleyville. As the last franchise in baseball to install stadium lights for night games, the Cubs' schedule still features more early afternoon starts than any other team in the league, and the sun-soaked ivy walls of Wrigley Field are a pleasure no matter what the score. Today, it's a rare thing in America: a genuine neighborhood ballpark, surrounded by streets that amplify the Cubs fandom into frenzy on game day. As a nightlife destination, Wrigleyville also supports the Metro, one of Chicago's foremost rock venues, and other great ones like Schuba's, Martyrs', and The Vic. The storefront theater scene also thrives here.
But there's more to Lakeview than Wrigleyville. A short walk east is Boystown, home of a cheerful, lively LGBT community and a great destination for anyone who enjoys high-energy nightlife. It's also home to the massive annual Pride Parade in June. Roscoe Village is west of Wrigley, and is popular with older gay couples and young people lured in by fashionable boutiques and the promise of a sunny day at one of the many sidewalk cafes on Southport, not to mention Chicago's premier movie revival house, the Music Box. And Lakeview embraces its inner dive bar in North Center, full of converted warehouses, quality bowling alleys and cheap beer without the jocks.

By train

The CTA Red Line makes stops in Lakeview (Belmont) and Wrigleyville (Addison, Sheridan). The Brown Line, further west, connects with the Red Line at Belmont, and makes additional stops in Lakeview (Diversey, Wellington, Southport), Roscoe Village (Paulina), and North Center (Addison, Irving Park). All but Sheridan are wheelchair accessible. The Purple Line from the Loop and Evanston also stops at Belmont during weekday rush hours.

By bus

• 8 Halsted travels through Boystown. A poll named this the worst bus route in the city. It's late when it shows up and goes nowhere fast.
• 9 Ashland is an all-night route. Overnight service only runs between 95th and the North/Clark Red Line stop.
• 22 Clark runs the length of the north side, but it slows to a crawl through Wrigleyville, particularly on weekends and on days of Cubs games. It runs all night long.
• 36 Broadway comes in from Uptown and carries on to the Loop.
• 49 Western runs all night through most of the city and hits the Belmont/Western intersection, near which is the best of the Roscoe Village nightlife.
• 76 Diversey runs east/west on Diversey, the border between Lincoln Park and Lakeview, and continues to Logan Square.
• 77 Belmont runs all night and connects Roscoe Village with the Belmont Red/Brown Line stop and Boystown.
• 80 Irving Park runs most of the east/west length of the city, connecting with the Brown Line in North Center and the Sheridan Red Line.
• 152 Addison travels east/west through the edge of Boystown, Wrigleyville, and on to North Center.

By car

Lake Shore Drive has an exit at Belmont. Beware of driving on Clark Street on weekends and during Cubs games, though. The taxis are a menace and the drunks are drawn to the middle of the street like flies to lights. You'll go nowhere fast and see Chicago at its worst in slow-motion.

• Horner Park

  phone: +1-773-478-3499
  address: 2741 W Montrose Ave
  Great big wonderful park with plenty of softball fields, football and soccer fields, basketball and tennis courts, trees, and a nice walking path. The leafy surroundings make it a great place for the annual pumpkin patch in the fall.

• Wunders Cemetery

  phone: +1-773-525-4038
  address: 3963 N Clark St
  Overshadowed by the magnificent Graceland Cemetery across the street in Uptown, the smaller, slightly overgrown Wunders was established in 1859 and features some intriguing monuments, with more of a forgotten-by-time atmosphere than its more famous neighbor. A third cemetery, Jewish Graceland, is directly south.

• Annoyance Theater & Bar

  phone: +1-773-697-9693
  address: 851 W Belmont Ave
  The Annoyance began with the long-running Co-ed Prison Sluts, which set the tone for what followed: fun, original shows with equal parts ironic kitsch and cheerful shock, led by Mick Napier, who directed some of Second City's best shows. The Annoyance is also one of the major training centers for comedy students in Chicago.

• Music Box

  phone: +1-773-871-6604
  address: 3733 N Southport Ave
  Chicago's foremost source of cinematic delight, with two screens for classic and world-premiere independent movies and the occasional mini-festival.

• Timber Lanes

  phone: +1-773-549-9770
  address: 1851 W Irving Park Rd
  If you like to sample the bowling culture of any city you visit, this is a fine choice; there are eight well-kept lanes, a cash bar, a good jukebox, and a few references to The Big Lebowski. Might be wise to call ahead for availability in the early evening, though, as there are a few leagues.

• Wrigley Field

  phone: +1-773-404-2827
  address: 1060 W Addision St
  Ernie Banks, Harry Caray, the 1908 champs, and the 2016 champs; yes, this is the home of the Chicago Cubs, the North Side's beloved baseball team. Among ballparks, only Fenway in Boston can match the old-time beauty of Wrigley and its famous ivy-covered walls. If you'd like to see Wrigley without attending a game, tours are occasionally offered ($25).

Music

A few great venues are also listed under Drink as well.

• Metro

  phone: +1-773-549-0203
  address: 3730 N Clark St
  Chicago's foremost rock venue, although other genres like electronic and hip hop figure in the lineup as well. If a band is on the verge of stardom and they're on their way through Chicago, the Metro has a knack for booking them. Many shows are all ages, and are generally affordable. Tickets general admission (e.g. standing room only), so be prepared to stand, and press forward for your right to see a guitarist's nostrils. Smart Bar, next door, is owned by the Metro and features good DJs most nights of the week.

• Schuba's

  phone: +1-773-525-2508
  address: 3159 N Southport Ave
  One of Chicago's landmark venues for cool music. The building was built over a hundred years ago by the Schlitz beer company, a heritage that is acknowledged by countless plastic cups serving that and other cheap beers for indie rock fans.

• Martyrs'

  phone: +1-773-404-9494
  address: 3855 N Lincoln Ave
  Artists in Chicago have developed communities in so many different genres — rock, blues, jazz, classical, hip hop, house, reggae, folk, country & numerous traditional ethnic style — that Martyrs' strives to be the place to see each of them.

• The Vic

  phone: +1-773-472-0449
  address: 3145 N Sheffield Ave
  The Vic hosts the Brew and View, a second-run movie theater with cheap Miller beer, and turns into a good concert venue on other nights — not dissimilar to the Metro in size or sound quality, but there are seats.

Theaters

• Briar Street Theater

  phone: +1-773-348-4000
  address: 3133 N Halsted St
  The Chicago home of the nationally famed performance art Blue Man Group. Shows in the evenings, with matinees included on weekends. If you've seen them elsewhere, you're not likely to see anything new here.

• The Playground

  phone: +1-773-871-3793
  address: 3209 N Halsted St
  The Playground has a few things going for it: the perfect location for beginning or ending the night with a show, a BYOB liquor license, and a non-profit co-op structure that makes the performers here some of the most enthusiastic and committed you'll find. Quality will vary by ensemble.

• Stage Left Theater

  phone: +1-773-883-8830
  address: 3408 N Sheffield Ave
  One of the mainstays of Chicago's storefront theater since 1982, Stage Left hosts everything: new works of social, political, intently serious drama are balanced out by manic rough drafts of new comedies by guest ensembles.

Events & festivals

• Pride Parade

  phone: +1-773-348-8243
  address: 3712 N Broadway St
  The annual celebration of Chicago's gay community, led by a parade down Halsted with floats and foam rubber contraptions that are not for the faint-of-heart. It's crowded, but it's a favorite of people from all over the city, and always high-energy. Most Boystown bars, clubs, and restaurants hold special events along with it. It gets very "lit"!

There are a few shopping areas of note. The Southport Corridor (3300 N to 3800 N) has a row of independent boutiques along with a few specialty stores. Lincoln Avenue in Roscoe Village also has some worthwhile shops, particularly near the Paulina Brown Line stop. Clark Street near Diversey has a few chain retailers like Marshall's, and a number of upscale boutiques are crammed alongside resale behemoths on Belmont, near the train station.
On game days, the streets of Wrigleyville are packed with vendors selling cheap Cubs gear.

• The Alley

  phone: +1-773-883-1800
  address: 843 W Belmont Ave
  The rock 'n roll shop in Chicago. Styles extend into punk, mod, emo, rockabilly, and goth; offerings range from clothes, shoes, and jewelry to bondage gear. It's the kind of edgy that is loved by no one as much as teenagers.

• Anthropologie

  phone: +1-773-935-2693
  address: 3532 N Southport Ave
  Librarian chic clothes boutique.

• The Brown Elephant

  phone: +1-773-549-5943
  address: 3020 N Lincoln Ave
  Find bargains on a large selection of second hand merchandise, including many upscale brands. All proceeds support HIV/AIDS care and gay and lesbian services.

• Century Shopping Centre

  phone: +1-773-929-8100
  address: 2828 N Clark St
  A vertical mall headlined by the Landmark's Century Centre multiplex showing independent and foreign movies, and several floors of stores from fashion chains like The Express.

• Gaymart

  phone: +1-773-929-4272
  address: 3457 N Halsted St
  With a large variety of gay-themed items — from sex toys to mouse pads and greeting cards — Gaymart is a must visit for Boystown shoppers.

• Ragstock

  phone: +1-773-868-9263
  address: 812 W Belmont Ave
  Cheap re-sale clothes shop. They also have a location in Wicker Park, but this one is open later (for those impulse fedoras) and has two floors.

• Twosided

  phone: +1-773-244-6431
  address: 2958 N Clark St
  Excellent selection of letterpress cards and other artful items, antiques, and one-of-a-kind objects. They also have a framing gallery in Andersonville, Foursided, but this one is a true gem.

It's not until you reach the high-end that Lakeview dining becomes especially memorable, but there are plenty of quick, reliable places. Most importantly, a lot of them are open late — this is probably the best place in the city to grab a bite after midnight.

Budget

• Bobtail Ice Cream Company

  phone: +1-773-880-7372
  address: 2951 N Broadway St
  Terrific locally-made ice cream at half the price of Cold Stone.

• Joy's Noodles and Rice

  phone: +1-773-327-8330
  address: 3257 N Broadway St
  Long standing Thai food restaurant on Broadway in Boystown. Numerous noodle, curry, and rice dishes at a very affordable price. BYOB, so stop at Treasure Islando before hand and get a nice bottle of wine to go with your meal. Good price on lunch specials, or use it as a great meal to start your night out on the town.

• Melrose Restaurant

  phone: +1-773-327-2060
  address: 3233 N Broadway St
  Open around the clock and always busy, the Melrose is a diner of modest culinary aspirations (burgers, omelettes) but it's right at the center of Boystown whether it's time for brunch or long past time to sleep.

• Nookie's Tree

  phone: +1-773-248-9888
  address: 3334 N Halsted St
  Casual, unpretentious diner that has been in Boystown for a long time. It's great for brunch, late-nights on weekends, and people-watching.

• Pick Me Up Cafe

  phone: +1-773-248-6613
  address: 3408 N Clark St
  Best known for being open late when you're too drunk to go anywhere else, this vegan friendly cafe has a variety of food from Mexican to pizza, and a nice selection of desserts.

• Penny's Noodle Shop

  phone: +1-773-281-8222
  address: 950 W Diversey Pkwy
  If you're looking for fast food, Penny's serves delicious Thai/Asian food and charges less than McDonald's.

• Salt n' Pepper Diner

  phone: +1-773-883-9800
  address: 3537 N Clark St
  This Wrigleyville greasy spoon has typical diner fare, but done in a way that makes it uniquely Chicago. The burgers are excellent, and so is the service.

• Satay

  phone: +1-773-477-0100
  address: 936 W Diversey Pkwy
  Decent Thai, Chinese, and Japanese food directly under the Diversey station. (It's never too loud, though.) The menu is surprisingly long for the size of the place, and they tend to do tofu notably well.

• Tac Quick Thai Kitchen

  phone: +1-773-327-5253
  address: 3930 N Sheridan Rd
  Good casual Thai food has been somewhat of a challenge in many parts of Chicago. This new BYO has succeeded when many other Thai restaurants have failed. Menu is available in both English and Thai.

Mid-range

• Angelina's Ristorante

  phone: +1-773-935-5933
  address: 3561 N Broadway St
  High-end Italian cuisine with a charming, intimate vibe. The pumpkin ravioli is a knockout.

• Ann Sather

  phone: +1-773-348-2378
  address: 929 W Belmont Ave
  This Swedish standby is a can't-miss for one of the city's best breakfasts, served all day, including warm, fresh-baked cinnamon rolls dripping with sugary icing. Now a bona-fide chainlet with five locations around Chicago, but try the nicely renovated 50-year-old Belmont branch.

• Cesar's Restaurant

  phone: +1-773-248-2835
  address: 3166 N Clark St
  Mind-blowing margaritas and Mexican food at a price that practically demands over-indulgence. There's another location nearby at 2924 N Broadway.

• The Chicago Diner

  phone: +1-773-935-6696
  address: 3411 N Halsted St
  A restaurant serving vegetarian-only food on Chicago's north side, the Diner's emphasis on quality — and its vegan shakes, which it proudly describes as "the shiznit" — has kept it around for more than 30 years.

• Chilam Balam

  phone: +1-773-296-6901
  address: 3023 N Broadway St
  Cash only BYO creative Mexican joint with a continuous line out the door for dinner. Known for fresh ingredients, moles, and small plates.

• La Creperie

  phone: +1-773-528-9050
  address: 2845 N Clark St
  Big, tasty crepes for breakfast, dinner, and dessert, with plenty of wine and beer. The outdoor seating is especially nice.

• Laschet's Inn

  phone: +1-773-478-7915
  address: 2119 W Irving Park Rd
  It began as a tavern, but now has a full kitchen for German food and meaty dinner specials.

• Mixteco Grill

  phone: +1-773-868-1601
  address: 1601 W Montrose Ave
  Someone finally figured out a historically cursed location. Excellent pollo en mole and other unique Mexican entrees in a slightly cramped setting. BYO. Friendly service once you sit down, but be patient with the host staff. Reservations recommended.

• New Tokyo

  phone: +1-773-248-1193
  address: 3139 N Broadway St
  A small, unpretentious sushi joint at the edge of Boystown, and BYOB as a bonus. The menu has a good variety for budget and taste.

• Que Rico!Great Mexican/Argentinean food with comfortable indoor and outdoor seating that can turns one hour into three before you ever think to look at your watch.

• phone: +1 773-975-7436
  address: 2814 N Southport Ave

• phone: +1 773 248-7426
  address: 2301 W Roscoe, Roscoe Village

Splurge

• Mia Francesca

  phone: +1-773-281-3310
  address: 3311 N Clark St
  The original location for Mia Francesca's fine Italian dining, and the best — it's noisy, crowded, and not the place for an intimate meal, but Mia's has great pasta & fish, and offers a very Chicago atmosphere of hustle & bustle.

• Tango Sur

  phone: +1-773-477-5466
  address: 3763 N Southport Ave
  Argentinean steakhouse with fantastic beef. There are a few side dishes like empanadas and a good dessert menu, but the beef is the star attraction. It's BYOB.

• Turquoise Restaurant

  phone: +1-773-549-3523
  address: 2147 W Roscoe St
  Extensive menu of fresh seafood, Mediterranean, and vegetarian specialties. Plenty of fruity and exotic drinks and lounging space on offer, too.

• Yoshi's Cafe

  phone: +1-773-248-6160
  address: 3257 N Halsted St
  Yoshi himself is a constant presence at the enormously popular local hangout. At times it seems as though half the restaurant knows Yoshi personally. Seasonal, creative entrees representing cuisine that stretches far from just an Asian influence. Nice, well-priced wine list as well.

Boystown

The nightlife in Boystown may be the best in Chicago. It's wild, uninhibited and just plain fun, regardless of sexual orientation. Most of the action is on Halsted/Broadway between Addison and Belmont.

• Charlie's

  phone: +1-773-871-8887
  address: 3726 N Broadway St
  Late night dance bar and a great place for the after hours party, although they play country for the early crowd before midnight on weeknights or 2AM on the weekends. Karaoke hits on Sunday and Thursday.

• The Closet

  phone: +1-773-477-8533
  address: 3325 N Broadway St
  Forgive the pun if you can — this lesbian dive bar is another great after hours destination and the place to go for hook-up attempts that drag late into the night. It's open a lot earlier in the day than most Boystown spots and usually has sports or music videos on by day.

• Cocktail

  phone: +1-773-477-1420
  address: 3359 N Halsted St
  A small, fashionable bar that anyone can walk right into for a drink at the bar or a dance among the eye candy at the back.

• Hydrate

  phone: +1-773-975-9244
  address: 3458 N Halsted St
  Inheritor of the space formerly owned by the infamous Manhole, Hydrate is now the ultimate dance club to See-and-Be-Seen on Halsted. On a night out in Boystown, everybody winds up here at one point or another.

• Roscoe's

  phone: +1-773-281-3355
  address: 3356 N Halsted St
  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.

• Sidetrack

  phone: +1-773-477-9189
  address: 3349 N Halsted St
  A large, stylish, multi-room bar that makes a great place to start the night, with slushy drinks and showtunes on a big screen. (Sundays are sing-along nights.) Gay or straight (but predominantly gay), this is one of the best bars in Chicago.

Wrigleyville

There is a watering hole for just about every personality type in Wrigleyville, particularly if you venture off the Clark Street drag near the ballpark. If you're here for a Cubs home game, rest assured that you'll be surrounded by thousands of merry Cubs fans and a world that desires nothing more than to put beer in your hands; on the downside, you'll be surrounded by thousands of Cubs fans and a world that desires nothing more than to spill beer on you, so get comfortable with sharing personal space with strangers. If you're drinking well into the night, choose wisely; as the evening wears on, a few of the bars on Clark turn into half-eaten piles of rancid nachos and the city's ripest gathering ground for date rape statistics.

• Bernie's Tavern

  phone: +1-773-525-1898
  address: 3664 N Clark St
  One of the most popular bars with locals and out-of-towners alike. The rather small inside bar opens to a large back patio. Crowd has gotten younger the past few years, but you'll still find fans from ages 20 to 90 having a good time.

• The Ginger Man

  phone: +1-773-549-2050
  address: 3740 N Clark St
  Guaranteed the only bar in Wrigleyville with Joy Division and Public Enemy on the jukebox. If you want a beer after a Cubs game and you don't want to be surrounded by frat boys, this is the place. Next to the Metro and Smart Bar.

• Goose Island

  phone: +1-773-832-9040
  address: 3535 N Clark St
  As the name suggests, you can drink the full range of the local Goose Island microbrews here, and it's reasonably spacious by Wrigleyville standards. Tasty food, too.

• Guthrie's Tavern

  phone: +1-773-477-2900
  address: 1300 W Addison Ave
  Cozy neighborhood bar known for its extensive collection of board games and bottled wines. It's a local favorite that escapes most of the obnoxious behavior found down the street.

• Murphy’s Bleachers

  phone: +1-773-281-5356
  address: 3655 N Sheffield Ave
  Granddaddy bar for all bleacher bums. Get there early if you want one of the coveted outside tables. It's always packed on game days; expect to pay $5 for a can of domestic beer. In the off-season, Murphy's turns into a rather cozy neighborhood bar.

• Nisei Lounge

  phone: +1-773-525-0557
  address: 3439 N Sheffield Ave
  Local cult favorite with an interesting Japanese backstory. No sushi here; just a great bar with a few pool tables.

• Piano Man

  phone: +1-773-868-9611
  address: 3801 N Clark St
  Popular local bar that has no piano, just a jukebox. Neighbors want to keep this place a secret, but the word has gotten out.

• Sluggers

  phone: +1-773-248-0055
  address: 3540 N Clark St
  Home away from home for suburbanites. Packed on game days; some say too packed. Sing to your heart’s content with the piano guys upstairs or get out your pent-up aggression from another Cubs’ heartbreaking loss in the batting cages.

• Trace

  phone: +1-773-477-3400
  address: 3714 N Clark St
  Less overtly sports-focused than its neighbors. Great place if you are thirsty at 3AM.

• Uncommon Ground

  phone: +1-773-929-3680
  address: 3800 N Clark St
  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.

• Yak-Zies Bar & Grill

  phone: +1-773-525-9200
  address: 3710 N Clark St
  Surprisingly good food at this cash-only joint. Owners will put just about any sport that’s televised anywhere on at least one TV if asked. Cornell vs. Harvard Men’s Ice Hockey anyone?

Others

Lakeview bars may get a bad name from the roiling mess on Clark Street, but there are actually several great places to drink within range of Wrigley.

• 404 Wine Bar

  phone: +1-773-404-5886
  address: 2852 N Southport Ave
  Comfortable atmosphere and a wide variety of wines. It may not be the first thing you think of when you think about a wine bar, but they serve a chicken pot pie that is delicious. It's connected to Jack's next door, which is more of a sports bar.

• Beat Kitchen

  phone: +1-773-281-4444
  address: 2100 W Belmont Ave
  There's beer and late-night food in the quiet front room, but the Beat Kitchen is worthy of recognition as one of the best venues in the city outside of Wicker Park for double or triple bills of excellent, little-known local and touring bands. Tuesdays are set aside for the Chicago Underground Comedy stand-up showcase.

• Hungry Brain

  phone: +1-773-935-2118
  address: 2319 W Belmont Ave
  There's a lot to like at this small Roscoe Village bar: a few pinball and arcade machines, the sense of being in someone's comfortable basement (with beer), and the Sunday night (10PM) Transmission series for improvisational and experimental jazz.

• Jake's Pub

  phone: +1-773-248-3318
  address: 2932 N Clark St
  A good place to recover from shopping binges at the Century Shopping Centre and its neighbors (see Buy). Jake's has a good beer selection and dependable jukebox. Dogs are not only welcome — they're encouraged.

• Katerina's

  phone: +1-773-348-7592
  address: 1920 W Irving Park Rd
  A small and intimate setting for jazz, funk, blues, and Greek music most nights, and poetry, performance and movies when there isn't music. Southern European cuisine served along with the drinks. Alas, Katerina's is closing at the end of June 2014. A new music and art venue is slated to take over the space.

• The Long Room

  phone: +1-773-665-4500
  address: 1612 W Irving Park Rd
  A low-lit neighborhood lounge with a casual atmosphere worth settling into for a while — and, yes, it's a very long room.

• Resi's Bierstube

  phone: +1-773-472-1749
  address: 2034 W Irving Park Rd
  A fine old-fashioned brauhaus, with high marks for the music, the beer garden, and the ambiance. Food on offer from the kitchen (closed Mondays) includes sausages and schnitzel, of course.

• Ten Cat Tavern

  phone: +1-773-935-5377
  address: 3931 N Ashland Ave
  The kitty on the sign is cradling a ten-ball because there's pool to be played here, but in most other respects, this is someone's apartment that happens to have a bar in it (and a pretty good backyard).

Most visitors will feel comfortable staying here in terms of safety, and Lakeview is a better place to experience something of the real city than the retail isolation of the Near North. Given the boozy atmosphere, though, it's probably better for singles and young couples than families with kids in tow. (You can get to Wrigley from anywhere in the city via the Red or Brown Line, after all.)
There are also a handful of budget and mid-range options just south of Boystown in Lincoln Park. Hotels are usually booked solid for the Pride Parade in June, so make reservations early or be ready to check in other areas.

Budget

• Wrigley Hostel

  phone: +1-773-597-4471
  address: 3514 N Sheffield Ave
  Very good hostel near Wrigley Field that is open 24 hours a day. Comfortable beds, free Wi-Fi, free breakfast and a common area with large screen TV and computers with Internet.

Mid-range

• Old Chicago Inn

  phone: +1-773-816-2465
  address: 3222 N Sheffield Ave
  Reasonably priced bed and breakfast in a turn-of-the-century greystone building, not far from Wrigley Field and the nightlife on Belmont. Amenities include internet access in the lobby, continental breakfast, and a complimentary lunch or dinner at Trader Todd's restaurant/karaoke bar two doors south.

• Villa Toscana Bed & Breakfast

  phone: +1-773-404-2416
  address: 3447 N Halsted St
  Closest accommodations to Wrigley Field, in a turn-of-the-century building.

Splurge

• Best Western Hawthorn Terrace

  phone: +1-773-244-3434
  address: 3434 N Broadway St
  83 rooms with wireless internet and a breakfast buffet. It's close enough to walk to Wrigley Field and the bars on Clark Street, but not close enough that you'll have to listen to them while you try to sleep.

• City Suites Hotel

  phone: +1-773-404-3400
  address: 933 W Belmont Ave
  Art Deco interiors and elegant furnishings, right next to the Belmont train station — so light sleepers may want to look elsewhere. Among the amenities are Wi-Fi, afternoon cookies, and access to Bally's Fitness Club.

• Majestic Hotel

  phone: +1-773-404-3499
  address: 528 W Brompton Ave
  Boutique hotel in a residential pocket, with olde worlde touches like poster beds and butler pantries. Similar amenities to the City Suites Hotel, which is under the same management.

• The Willows Hotel

  phone: +1-773-528-8400
  address: 555 W Surf St
  European decor in a city-designated landmark building, two blocks from the lake. Same management as the City Suites and Majestic hotels.

• Lincoln/Belmont Library

  phone: +1-312-744-0166
  address: 1659 W Melrose St
  Free public internet access. Three blocks south of the train station.

• Merlo Library

  phone: +1-312-744-1139
  address: 644 W Belmont Ave
  Free public internet access. Three blocks east of the train station, near Boystown.

• If it's a crosstown baseball series, you'll need to get on the Red Line and head south to Bridgeport for the Chicago White Sox.
• It would take more than one curse to put the Cubs in their current condition, but the most famous of them, the Billy Goat Curse, began with the owner of the Billy Goat Tavern in the Near North.
• Follow the theater trail in the storefront comedy direction to Uptown or the big-name comedy/drama direction in Old Town.
• Andersonville is a stylish neighborhood a short trip northwest of Boystown with several gay and lesbian-friendly bars and businesses.
• Edgewater has the GLBT Gerber/Hart Library and the less scholarly Leather Archives and Museum. During the summer, Chicago's gay community tans at Edgewater's Hollywood Beach.
• Dedicated to original theater that explores gender and sexual identity, the About Face Theater Company performs at major theaters like Steppenwolf in Old Town and storefronts around Boystown.