Uptown is a scruffy, jazz-inflected neighborhood on the north side of Chicago. Within its boundaries, off to the side of the action, are the residential areas of Sheridan Park and Buena Park, and an exciting Southeast Asian community based around Argyle Street.
This article also includes Andersonville, a short walk to the north, which is an upscale, lesbian-friendly neighborhood.
"Eternal Silence" by Lorado Taft, Graceland Cemetery
Uptown is the result of a divine message received by men with a tremendous amount of money in the early 1920s. Here, by the lake, there was to be an entertainment district of such magnificence that it would shift the entire center of Chicago to the north, and within a few years, overtake even Manhattan for supremacy in the nation. Up went canyons of Art Deco magnificence: hotels, department stores, palaces of music and the arts; all in accord with the vision. Ever see a movie where cigar-chomping gangsters escort gorgeous molls into a damn good jazz club? That's The Green Mill. Where thousands of earnest teens dance their hearts out for a famous live radio broadcast? That's the Aragon Ballroom. And the crowning achievement was the Uptown Theatre, where every man could see a movie like a king.
But there was the small matter of the stock market crash in 1929. Right as Uptown was reaching its peak, new construction slammed to a halt and Uptown never recovered. Needing tenants, many buildings were carved up for low-income housing, and maintenance was lowered to match the rent. There was still revelry, but it was seedier, and less of a destination for the fresh-faced teens of yesteryear. Unlike other parts of the city, which were reinvented by changing fortunes across the decades to come, Uptown stayed on the mat, beaten down by poverty.
At last, though, Uptown is reaping the rewards of that heritage. Years of cheap living created a diverse community that's still resident there today, highlighted by the amazing Southeast Asian pocket on Argyle between Sheridan and Broadway. (It's sometimes mistakenly known as "Little Saigon" or "North Side Chinatown," but it's too diverse for one label.) For the first time in decades, the entertainment district is growing again, with the survivors holding strong and joined by some great new options. In an area where a dilapidated pancake house from the 1950s still counts as new construction, the seedy atmosphere of Uptown can be absorbing like few others in the city, and makes for a memorable night out.
Andersonville hasn't experienced the highs or the lows of Uptown, and strikes a completely different vibe. Originally a hub for Swedish immigrants, whose influence can be seen in a few restaurants and bars, it became a hub for Chicago's lesbian community, and today has a less raucous atmosphere than the younger GLBT scene in Boystown. The stylish boutiques and inviting restaurants have made it a great place for people of all backgrounds to live, and a laid-back destination for shopping or entertainment, particularly at the Neo-Futurarium, Chicago's most inventive original theater.
Uptown is well-served by public transportation from the center of the city, with all of the sights and nightlife within an easy walk of the train. The CTA Red Line runs from the Loop through Uptown (Wilson, Lawrence, Argyle) and near Andersonville (Berwyn). These are some of the CTA's oldest and worst-kept stations, so accessibility for handicapped travelers will be a major issue — plan to connect a bus instead. (The Addison Red Line station in Wrigleyville is the closest fully-accessible station.)
The walk from any of the Uptown Red Line stations to Clark Street and Andersonville is no real bother except in the winter, when you're better off waiting inside the station for a bus (see below).
22 Clark also runs all night on Clark Street from Edgewater (to the north) and on to Lakeview (to the south).
36 Broadway also runs from Edgewater (to the north), passing by the concert venues and the Southeast Asian stores, and from there to eastern Lakeview. It's only a half-block walk from the Red Line stops.
50 Damen runs along Damen from the Brown Line and Ashland, north of Foster, near the western edge of Andersonville.
78 Montrose connects with the Brown Line in North Center and the Wilson Red Line in Uptown.
80 Irving Park runs along Irving Park. Connections can be made with the Irving Park Brown Line stops as well as the Sheridan Red Line.
81 Lawrence connects with the Red Line station of the same name and operates all night. You won't need the bus to reach the concert venues, but it does run through Albany Park and to the Jefferson Park Blue Line station.
92 Foster connects with the Red Line at Berwyn and is the best way to reach Andersonville from the train. It also ends up west at the Jefferson Park Blue Line station.
145 Wilson/Michigan Express runs all-stops as far west as Damen, connecting with the Ravenswood Metra station, and then runs express on Lake Shore Drive to the Near North and the Loop.
151 Sheridan is a local route from downtown, running all-stops down Sheridan Road. It's an all-night route.
Train in vain
On a transit system full of oddities and abnormalities, the Wilson Red Line station has to be near the top of the list. The marble steps and ornate facade are hopelessly cracked and water-damaged, and the only places that are remotely well-lit are the food mart and the fried chicken restaurant. With some effort, you can mentally reverse the decayed grandeur and imagine the station as it was in 1923, when it replaced an inferior structure built by some dink named Frank Lloyd Wright. Originally, this was the northern terminus for the CTA, and an extra platform was built for passengers changing to the North Shore Line for transit further north. When the CTA took over the full system, the extra platform was stripped of its canopy and abandoned, and has remained that way ever since, with not even a billboard by the ad-happy CTA to adorn it. Believe no rumors of a magical express boarding over there...
The best way to reach Uptown by car is the fabled Lake Shore Drive, which has exits at Wilson, Lawrence, Foster, and Bryn Mawr ending at Sheridan and Hollywood in Edgewater. Drive a few blocks west from any of these and you're at Broadway, the main street in Uptown.
Clark Street is the main drag for Andersonville, with a few sights on Ashland, a short walk to the west.
Uptown is rich with Art Deco buildings large and small, albeit in varying stages of preservation or neglect. The Wilson Red Line station is worth a look for the arch over the original entrance at the corner of Wilson & Broadway, into which a Popeye's Chicken has been incongruously crammed. Tourists who are crows will find this arch especially enjoyable, judging from the number of crows that spend time here. In much better shape is the Bridgeview Bank Uptown at Lawrence and Broadway, the tallest building in the area, with a well-kept green and white facade. The old Goldblatt's Department Store at 4718 N Broadway had been carefully renovated on the outside for a Borders bookstore, which has since closed. Back on the other end of the scale is the magnificent sandstone Uptown Broadway Building at 4707 N Broadway, crumbling and covered in netting for a possible (expensive) renovation.
Another worthy stroll for architecture enthusiasts is the Hutchinson Street District, from 600-900 W Hutchinson, closer to the lake. It's the post-Mies apartment blocks that dominate the Uptown skyline from the lake, but Hutchinson has some lovely street-level Prairie School houses by George Maher.
Essanay Studios, 1333-45 W Argyle St (Argyle Red Line). From 1907-17, Hollywood was in Uptown. A dizzy list of silent movie giants shot films here, Charlie Chaplin and local girl Gloria Swanson among them, and the city's awful winters played a part in shifting production to California for part of the year. When Chaplin left, the studio collapsed, and California started seeming more attractive year-round. The building is now a protected landmark, and houses the bi-lingual St Augustine College . No tours are available, but check out the grand name above the doorway.edit
Graceland Cemetery, 4001 N Clark St (Sheridan Red Line), ☎ +1 773 525-1105, . Grounds 8AM-4:30PM, office 8:30AM-4:30PM. A stunner. Chicago history lies in rest here, from the major names (Burnham, Sullivan, Field, Pullman, Mies) to the footnotes (Charles Dickens' obscure brother Augustus). Some credit Sullivan's 1890 design for the Getty Tomb as the opening act of modern architecture. (And Inez Clarke's grave is one of the most famous "haunted" spots in Chicago.) The new (and warm) office can supply a map for the grounds, which are quite large. Come with time to wander.Free. edit
Japanese American Service Committee, 4427 N Clark St (22 Clark bus), ☎ +1 773 275-0097, . Hours vary. A social services agency for the Chicago Japanese community with occasional exhibits of interest, such as a collection of photos and art relating to internment camps during World War II. Festivals and cultural events also pop up from time to time.edit
South-east Asia Center, 5120 N Broadway St, 1124 W Ainslie (Argyle Red Line), ☎ +1 773 989-6927, . M-F 8:30AM-5:30PM. Not a tourist sight, necessarily, but a center for the local South-east Asian community, young and old. Ten languages (besides English) are spoken by the staff. Volunteer opportunities like English teaching and elderly care abound.edit
Swedish American Museum Center, 5211 N Clark St (Berwyn Red Line), ☎ +1 773 728-8111, . Tu-Fri 10AM-4PM, Sa-Su 11AM-4PM. Celebrates Swedish-American heritage and Swedish immigration in all its forms, including Buzz Aldrin's temporary immigration to the moon.$4 adults, $3 kids. edit
Uptown has one of the best collections of concert venues in Chicago, most of which are renovated holdovers from the area's Roaring Twenties heyday.
One that isn't renovated is the huge Uptown Theatre on Broadway. It was built by the Balaban and Katz movie kings in 1925 to be as lavish as possible, and when it opened, it was described as "an acre of seats in a magic city," second only to Radio City Music Hall in size. With the declining fortunes of the neighborhood, it was shuttered in the early 1980s, and has remained in limbo ever since; too expensive to demolish, but too expensive to fix. It could yet be restored, although it would be a difficult task, especially with the still-shaky state of the Uptown economy. Until something happens, the majestic facade and marquee will peer out over Broadway, eerie in the darkness.
Aragon Ballroom, 1106 W Lawrence Ave (Lawrence Red Line), ☎ +1 773 561-9500, . Box office M-F 9AM-6PM. Built in 1926 with an interior that is meant to recreate a Spanish palace courtyard, the Aragon cost more than two million dollars at the time, and the well-preserved interior still has the otherworldly brilliance. It shifted from big-band sensation to prizefight arena and swinging mod disco, but it's been in good hands for more than thirty years now, as promoters for Latin dances and rock shows split nights of the week.edit
The Green Mill, Uptown
The Green Mill, 4802 N Broadway St (Lawrence Red Line), ☎ +1 773 878-5552, . M-Sa noon-4AM, Su noon-4AM. Jazz and lots of it at this Uptown landmark, famously an old hangout of Al Capone (who's not, though, around as much as he used to be). Go on a Sunday evening for the weekly poetry slam. National talent Patricia Barber  performs on most Mondays along with a few other excellent resident ensembles.Covers usually less than $10. edit
The Riviera, 4746 N Racine Ave (Lawrence Red Line), ☎ +1 773 472-0449, . Box office opens when doors open for the night's show. Probably the only old Balaban and Katz movie palace that's still in full use as a nightly entertainment venue, mostly for all-ages punk and indie rock bands, but occasionally hip-hop as well. There are seats in the balcony, but the main floor is standing room only. Stay behind the rail to stay out of the mosh pit (should one begin).edit
Annoyance Theater, 4840 N Broadway St (Lawrence Red Line), ☎ +1 773 561-4665, . 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.Tickets $5-15. edit
Black Ensemble Theater, 4520 N Beacon St (Wilson Red Line), ☎ +1 773 769-4451, . Sa 8PM, Su 3PM. Committed to building racial bridges through telling stories of African-American history to a cross-cultural audience. If that sounds stodgy, consider how they do it: recent productions have included Memphis Soul, a full-scale resurrection of the sound and story of Stax Records.$40. edit
Neo-Futurarium, 5153 N Ashland Ave (Berwyn Red Line), ☎ +1 773 275-5255, . F-Sa 11:30PM, Su 7PM, closed last two weeks of December. Andersonville — and the second floor of the Nelson Funeral Home, to be precise — is the home of the long-running late-night show Too Much Light Makes The Baby Go Blind and its ever-changing menu of the funny, the profound, and the occasional tongue bath for a 20th century European ethos, intended to be accomplished within the confines of thirty plays in sixty minutes. Arrive early — people are turned away almost every week.No advance tickets; admission is $9 plus the roll of a six-sided die. edit
Montrose Beach, 4400 N Lake Shore Dr (Wilson Red Line). Uptown got short-changed when it comes to beaches compared to its neighbors on the north and south, but this is what's there, a short walk east on Wilson. One bonus: it's officially Dog Friendly. The smaller Foster Beach is a few blocks north at 5200 N Lake Shore Drive.edit
The People's Music School, 931 W Eastwood Ave (Argyle Red Line), ☎ +1 773 784-7032, . M-W,F noon-7:30PM, Th noon-8PM, Sa 9AM-3PM, Su closed. For a distinctly non-seedy music experience, try the kids-friendly classical and world music concerts at this community-based not-for-profit music school.Concerts free, but donations welcome. edit
You'll find several cute, stylish clothes boutiques for women in Andersonville. With the number of cafes and bakeries sharing the streets, it's a great place to shop, stop, and shop again.
The Brown Elephant, 5404 N Clark St (22 Clark bus), ☎ +1 773 271-9382, . 11AM-6PM daily. A thrift shop that makes a difference: All proceeds benefit the Howard Brown Health Center, a health care center that serves the needs of the LGBT community and the HIV/AIDS community in Chicago. The selection is more hit than miss, so it's worth a look.edit
Early to Bed, 5232 N Sheridan Rd (Berwyn Red Line), ☎ +1 773 271-1219, . Tu noon-7PM, W-Th,Sa noon-8PM, F noon-9PM, Su noon-6PM, M closed. Lesbian-owned, female-oriented sex shop without the sleaze. They hold weekly workshops on topics ranging from erotic writing to strategies for, well, you know. Check the schedule on the website (mostly Tuesdays).Workshops are $15/$10 students, reservations required. edit
Foursided, 5061 N Clark St (22 Clark bus), ☎ +1 773 506-8300, . M-W 11AM-7PM, Th-Sa 10AM-7PM, Su 11AM-5PM. An eclectic framing shop with a fun selection of cards, one-of-a-kind treasures, and found-art assemblages by the staff and local artists that's worth a look.edit
Shake, Rattle & Read, 4812 N Broadway St (Lawrence Red Line), ☎ +1 773 334-5311, . M-Sa noon-6PM, Su noon-5PM. A pop culture emporium and a labor of love for the owners, this store has dense warrens of used paperbacks, pulp novels and vinyl records (78 and 45rpm), mostly jazz, with a sealed-in-plastic selection of memorable news magazines on the wall and porn magazines on a rack toward the back. If you want a peek into the heart of Uptown or just a paperback to last until your next stop, this is the place.edit
Women and Children First, 5233 N Clark St (22 Clark bus), ☎ +1 773 769-9299, . M-Tu 11AM-7PM, W-F 11AM-9PM, Sa 10AM-7PM, Su 11AM-6PM. This is one of the foremost feminist bookstores in the country, with more than 30,000 books and a regular schedule of events and author appearances. (Hillary Clinton is among the roster of guests.) If you have kids in tow, bring them to Storytime on Wednesday mornings (10:30-11AM).edit
With the glory days of Goldlbatt's long past, Uptown isn't much of a destination for shopping — save, of course, for the Asian imports on and around Argyle.
A-Z Wallis Army Navy Store, 4647 N Broadway St (Wilson Red Line), ☎ +1 773 784-9140, . M-Th 9:30AM-5:45PM, F 9:30AM-6:45PM, Sa 9AM-5:45PM, Su 10AM-3:45PM. Has about a dozen names, but the idea remains the same: this is one of the oldest Army surplus stores in Chicago, and a pretty big one at that. It also doubles as a "discount department store," so there are some cheapster watches and the like.edit
Tai Nam Market Center, 4925 N Broadway St (Argyle Red Line), ☎ +1 773 275-5666, . Hours vary by store. Under the red arch on Broadway near Argyle, this strip mall has outlets for Vietnamese, Chinese & Thai restaurants and groceries, nail & skin care, and imported jewelry, music and videos.edit
Tan Thana Gift Shop, 1135 W Argyle St (Argyle Red Line), ☎ +1 773 275-8687. M-F 9AM-6PM, Sa-Su 9:30AM-6PM. Packed to the rafters with statues, pottery, and other Asian gift items. Trung Tin, a block east at 1057 W Argyle, also has a big selection.edit
The Tattoo Factory, 4441 N Broadway St (Wilson Red Line), ☎ +1 773 989-4077, . 10AM-2AM daily. Uptown after dark is the kind of place that inspires a tattoo (or a piercing). According to the owners, this is the oldest continually operating tattoo parlor in Chicago.edit
Uptown Bikes, 4653 N Broadway St (Wilson Red Line), ☎ +1 773 728-5212, . M-Tu,Th-F 11AM-7PM, Sa-Su 11AM-5PM, W closed. If you're biking through Chicago, this is a great place for parts, accessories, or quick repair. There are some neat custom bikes for sale, but no rentals.edit
Argyle is the wonderland. The Red Line drops you right in the midst of it — three blocks, from Sheridan to Broadway, of cheap and delicious Asian food. If you believe in eating where the locals eat, Argyle is most certainly the place to go; this is authentic cooking, with no tourist traps to be found. Vietnamese restaurants and bakeries are the most plentiful, with various disciplines of Chinese food a respectable second, and Thai dishes included on the menus of several non-Thai restaurants. Happily, there's a Laotian option in the neighborhood as well.
Cafe Hoang, 1010 W Argyle St (Argyle Red Line), ☎ +1 773 878-9943, . M,W-Th 11AM-10PM, F-Sa noon-10:30PM, Su noon-10PM, Tu closed. 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.$8-12. edit
Dong Thanh, 4925 N Broadway St (Located in Tai Nam Market Center), ☎ +1 773 275-4928. M 8AM-4PM, Tu-Su 8AM-8PM. BYOB restaurant named for the city by the same name in Vietnam. They take pride in customizing spice levels to suit your taste.$6-8. edit
Furama Restaurant, 4936 N Broadway St (Argyle Red Line), ☎ +1 773 271-1161, . Su-Th 9:30AM-9:30PM, F-Sa 9:30AM-10PM. Dim sum, Mandarin, and Cantonese in comparatively palatial second-floor digs. Furama is the biggest and has the most conventional menu of the Argyle Asian restaurants, but that doesn't mean it isn't good.$8-10. edit
Pho 777 (House of Noodle), 1065 W Argyle St (Argyle Red Line), ☎ +1 773 561-9909. M,W-F 9:30AM-10PM, Sa-Su 9AM-10PM, Tu closed. Pho is widely available on Argyle, but it's a serious matter in the two big, green rooms of the House of Noodle. Pho supremacy between this and Tank Noodle below is a hot topic of local debate. BYOB.$5-10. edit
Pho Xe Tang (Tank Noodle Restaurant), 4953 N Broadway St (Argyle Red Line), ☎ +1 773 878-2253, . M-Tu,Th-Sa 8:30AM-10PM, Su 8:30AM-9PM, W closed. Pleasant, tourist-friendly restaurant that serves a suitably wide range of variations on pho and a few other Vietnamese and Chinese dishes, right on the corner of Argyle and Broadway.$5-12. edit
Sun-Wah BBQ, 5041 N Broadway St (Argyle Red Line), ☎ +1 773 769-1254, . Su-W 9AM-9PM, F-Sa 9AM-10PM, Th closed. Among the top culinary treasures on Argyle. Where others might bother with plants, Sun-Wah keeps a few rows of roast birds in the front window. The duck is obviously the headliner, but the pork earns acclaim as well. Order the duck from the to-go window and get a cheaper, more delicious, option.$8-10. edit
Hon Kee, 1064 W Argyle St (Argyle Red Line). W-M 9AM-9PM. This is another good place for Chinese BBQ.edit
Thai Avenue, 4949 N Broadway St (Argyle Red Line), ☎ +1 773 878-2222, . M-Th 11AM-9:30PM, F-Sa 11AM-10PM, Su 11AM-9PM. Features the longest Thai-language menu in the area. They have popular lunch specials.$6-8. edit
Thai Pastry, 4925 N Broadway St (Located in Tai Nam Market Center), ☎ +1 773 784-5399, . Su-Th 11AM-10PM, F-Sa 11AM-11PM. 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.$8-10 (meal). edit
Siam Noodle and Rice, 4654 N Sheridan Rd (Lawrence Red Line), ☎ +1 773 769 6694, . Tu-Th 11AM-9PM, F 11AM-9:30PM, Sa 11:30AM-9:30PM, Su 11:30AM-8PM, M closed. Excellent family-owned homestyle Thai cafe; an Uptown favorite.$6-9. edit
Vinh Phat BBQ, 4940 N Sheridan Rd (Argyle Red Line), ☎ +1 773 878-8688. 9AM-7PM daily. There are two sides to this Vietnamese BBQ: birds and bread. The baguettes are priced at a very Vietnam-like three-for-1, while the BBQ'd birds get chopped up into bánh mì sandwiches.$1-6. edit
Ba Le Bakery, 5016 N Broadway St (Argyle Red Line), ☎ +1 773 561 4424, . 7:30AM-9PM daily. Specializing in Vietnamese bánh mì sandwiches. Cheap and delicious!$4-7. edit
Cheap fast food can be found around the Wilson Red Line station, but there are several better options for eating well on a budget.
Alma Pita, 4600 N Magnolia Ave (Wilson Red Line), ☎ +1 773 561-2787, . M-F 11AM-9PM, Sa 11AM-8PM, Su closed. Mom & Pop Middle Eastern, Lebanese and Indian restaurant. There's a $5 vegetarian special, and the tilapia fish curry is a house specialty.$4-9. edit
Gigio's, 4643 N Broadway St (Wilson Red Line), ☎ +1 773 271-2273. Su-Th 9AM-midnight, F-Sa 9AM-2AM. Really good greasy thin-crust pizza by the slice — never mind the way the place looks. It's open late in case you're hungry after a show at the Green Mill, the Aragon or the Riviera on the other side of the tracks.$2.50-13. edit
Nigerian Kitchen, 1363 W Wilson Ave (Wilson Red Line), ☎ +1 773 271-4010. M-Sa 11AM-10PM, Su closed. Not much for atmosphere, with a loud television hanging over the sparsely decorated dining area, but it's one of Chicago's few sources for yam-heavy Nigerian food, and BYOB too.$4-11. edit
Palace Gate, 4548 N Magnolia Ave (Wilson Red Line), ☎ +1 773 769-1793. M-W 10AM-8PM, Th-Su 10AM-9PM. In Ghana, it's considered a taboo to eat in public without inviting others to join you, so don't come to Palace Gate looking for solitude with your fufu dumplings. The decor is plastic and basic, but the atmosphere is merry.$8-10. edit
Svea, 5236 N Clark St (22 Clark bus), ☎ +1 773 275-7738. M-F 7AM-2:30PM, Sa-Su 7AM-3:30PM. Swedish breakfast spot with renowned lingonberry pancakes.$4-9. edit
Ann Sather, 5207 N Clark St (22 Clark bus), ☎ +1 773 271-6677, . M-F 7AM-2PM, Sa-Su 7AM-4PM. Chicago's most popular Swedish chainlet has to get a mention in formerly Swedish Andersonville. The weekend brunch lines can be long, but see if you're sorry when the homemade cinnamon rolls arrive.$10-14. edit
Hamburger Mary's, 5400 N Clark St (22 Clark bus), ☎ +1 773 784-6969, . 11:30AM-11PM daily. Legendary burgers, fried twinkies and plenty more.$8-12. edit
Inspiration Kitchens, 4715 N Sheridan Rd (Lawrence Red Line), ☎ +1 773 275-0626, . W-F 8AM-10PM, Sa 9AM-10PM, Su 9AM-2PM. Inspiration Kitchens has the longest lines you'll find in Uptown, and that's for a good reason: everything on the menu is prepared and served by former homeless people in a culinary training program. It's organized through the Inspiration Corporation at 4554 N Broadway, which is a great place to volunteer for a day.$9-17, BYOB. edit
Jin Ju, 5203 N Clark St (22 Clark bus), ☎ +1 773 334-6377, . Su,Tu-W 5-9:30PM, Th 5-10PM, F-Sa 5-11PM, M closed. Possibly the only Korean food in Chicago outside of Seoul Drive. Seafoodies and vegetarians will do equally well; if unsure, try the bulgogi, and resolve all of life's other uncertainties with a round or two of soju.$12-20. edit
Silver Seafood, 4829 N Broadway St (Argyle Red Line), ☎ +1 773 784-0668, . 11AM-1AM daily. Hong Kong-style seafood, some of which comes out of the tank at the back of the banquet-style dining room. Whether this meal is a mid-range or a splurge depends on how deep into the Chinese-only menu you'd like to go. It's just down the block from the Argyle Asian restaurants.$6-58. edit
Tweet...let's eat, 5020 N Sheridan Rd (Argyle Red Line), ☎ +1 773 728-5576, . 8:30AM-3PM daily. Brunch only, with organic materials. Try the quiche platter ($14) or the lox ($12). Free wi-fi and parking. Cash onlyedit
Hopleaf in Andersonville (see Drink) deserves consideration for anyone looking for a terrific meal (with beer included).
Agami, 4712 N Broadway St (Lawrence Red Line), ☎ +1 773 506-1845, . Su-Th 5-11PM, F-Sa 5PM-1AM. Sushi, maki, and cooked Japanese fare that lives up to the prices and fancy decor. There's a full bar, and a $15 corkage fee per bottle of wine will apply for BYOB.$16-30. edit
Magnolia Cafe, 1224 W Wilson Ave (Wilson Red Line), ☎ +1 773 728-8785, . Tu-Th 5:30-10:30PM, F-Sa 5:30-11:30PM, Su 10AM-3PM, 5-9PM. Upscale bistro with the warm decor, live jazz, varied menu and valet parking worthy of stretching your budget.$14-32. edit
Spacca Napoli, 1769 W Sunnyside Ave (Montrose Brown Line), ☎ +1 773 878-2420, . Tu 5-9PM, W-Th 11:30AM-3PM,5-9PM, F 11:30AM-3PM,5-10PM, Sa 11:30AM-10PM, Su noon-9PM, M closed. If you're weary of the pizza struggle between Chicago and NYC, side with the Sicilians at this fantastic Neapolitan restaurant and their excellent wine list.$15-25. edit
Kopi, 5317 N Clark St (Berwyn Red Line), ☎ +1 773 989-5674. M-Th 8AM-11PM, F 8AM-midnight, Sa 9AM-midnight, Su 10AM-11PM. 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.edit
If you're looking for a drink in Uptown, don't forget to raise a glass at the Green Mill (above).
Big Chicks, 5024 N Sheridan Rd (Argyle Red Line), . M-F 4PM-2AM, Sa 3PM-3AM, Su 10AM-2AM. Gay-friendly bar in Uptown, with a dance floor, plenty of food, and a fine beer garden.edit
Crew, 4804 N Broadway St (Lawrence Red Line), ☎ +1 773 784-2739, . M-W 11:30AM-midnight, Th-F 11:30AM-2AM, Sa 11AM-2AM, Su 11AM-midnight. Gay sports bar & grill — check the "I Love Tight Ends" t-shirts on the bar staff. It's a great place to watch a game, and parties are ready to erupt on Friday and Saturday nights. Good food, too.edit
Fat Cat Bar & Grill, 4840 N Broadway St (Lawrence Red Line), ☎ +1 773 506-3100, . M-F 4PM-2AM, Sa 11AM-3AM, Su 11AM-2AM. Brand new and very popular, with decor and cocktails that attempt to evoke the Art Deco class of the original Uptown.edit
Hopleaf, 5148 N Clark St (Berwyn Red Line), ☎ +1 773 334-9851, . Su-F 3PM-2AM, Sa 3PM-3AM. Fantastic selection of beer, with a surprisingly accessible menu for delving into the world of Belgians and local microbrews. The food is great, especially the steamed mussels, but the beer is even better. It's pricey, though. Make sure to come early, The Hopleaf is popular and usually packed. The monthly Bookslut Reading Series is held upstairs.edit
Simon's Tavern, 5210 N Clark St (22 Clark bus), ☎ +1 773 878-0894, . Su-F 11AM-2AM, Sa 11AM-3AM. Simon's has roots as a Prohibition-era speakeasy and a Swedish hangout (from which, rumor has it, Norwegians were barred). Today, there's cheap beer on tap and vikings among the unpretentious decor. edit
Don't book a room in Uptown with expectations of that old swingin' class — most of these rooms are used by transients and homeless people getting back on their feet, and should only be considered by travelers as rock-bottom budget options. Nearby Edgewater has a few nice, gay-friendly B&Bs, though.
Darlington Hotel, 4700 N Racine Ave (Lawrence/Wilson Red Line), ☎ +1 773 561-1741. On a residential street, a short walk from the Green Mill, the Riviera, and other Uptown music venues. Rooms vary — some have sinks, some have baths, other have neither.$45 per night with a $30 key deposit. edit
Andersonville is safe more or less around the clock, as long as you use basic city common sense. Uptown can be a risky proposition after dark, though, especially near Wilson Avenue. You'll be fine walking between the concert venues to the CTA, but save any architecture walks for earlier in the day. A lot of transients and homeless people live in Uptown, where there are some drug/alcohol rehab centers. So while the overall crime rate is not high compared to some other parts of the city, it's advisable to be aware of your surroundings, even in daylight.
If it's jazz history that brought you here, don't forget Bronzeville, which in its day was home to Louis Armstrong and Chicago jazz in its golden age. If you care less about the history, however, and just want to hit the current top jazz clubs, head down to the Velvet Lounge in the Near South, which should not disappoint.
For a more expensive theater experience, the prices rise as you head south through Lakeview and Old Town.
If the GLBT scene in Andersonville leaves you wanting more, head south on Clark and then a couple blocks east towards Boystown.
If you had a good time on Argyle, the Red Line can take you straight to Chinatown on the South Side.
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