Windy City Confidential: 50 Unusual Chicago Destinations

Intro

Typically we encounter Chicago through sports and music, film and television. We know the Bulls and Michael Jordan; Common and Kanye walked us around the bitterly cold corners of the Chi's South Side; years and years ago, Robert Johnson sang of the city in his instantly recognizable high and keening voice. Christopher Nolan turned the skyscrapers and streets into Gotham for Batman Begins and The Dark Knight, and ER showed us what a bloody nightmare the inside of Chicago's hospitals are. But where do you get at the real city, the neglected places, the spots left uncovered by popular culture?

Cue up this list. Complex has scoured the blocks of the Midwest's biggest city, checking down alleyways and lifting manholes to get at the teeming life beneath. For an insider's take, here is Windy City Confidential: 50 Unusual Chicago Destinations.

(For more of Megan's work, check out her tumblr.)

RELATED: Green Label - The Best Live Music Venues in Chicago

Blues Brothers bridge (East Chicago)

50. Blues Brothers Bridge (East Chicago)

Location: 3300 East 95th St.

When it's dark and you're wearing sunglasses, it's time to head south to what the natives call “East Chicago,” to the 95th Street drawbridge. Built in 1958 and memorialized in The Blues Brothers “bridge jump” scene, you can feast both on movie-awesomeness and some killer smoked fish at Calumet Fisheries (3259 East 95th St.), right next door. This little shack of a place was recently honored big-time with a James Beard award and featured on Anthony Bourdain's No Reservations—if you go, you'll see why.

Northerly Island

49. Northerly Island

Location: 1400 South Lynn White Dr.

This little parcel of land has quite a tumultuous past. Part of architect Daniel Burnham's early 20th century “Plan of Chicago” vision for the city, this lakefront park became home to tiny airstrip Meigs Field. Until, that is, the runway was destroyed after post-9/11 fears got the better of then-Mayor Daley, who had the tarmac ripped up in the middle of the night (dubbed the “Midnight Raid”). Now, this 91-acre peninsula (not really an island at all) is a recreation spot for hiking, fishing, and (in the winter) snow-shoeing and cross-country skiing. The terminal and control tower are still there for the time being, until the area is rehabbed to include off-shore reefs and an open-air music pavilion.

Bucket Boys

48. Bucket Boys

For years, this group of South Side teens has regaled passersby with their street performances— sitting on plastic crates facing overturned plastic buckets, drum sticks in hand, and with more synchronization than you might expect. You'll usually find them on Michigan Avenue, just outside the Wrigley Building, and they've since expanded to the other Wrigley (Field, that is). In 2002, they were discovered by a representative from the Chicago Bulls, who invited them to perform during a home game. They haven't moved to Hollywood, yet. You'll still find them entertaining the masses around town.

Windy City Skaters @ North Ave. Beach

47. Windy City Skaters at North Ave. Beach

Location: 1600 North Lake Shore Dr.
Website: meetup.com

For some impressive in-line feats, or a bit of instruction, catch the Windy City Skaters doing their thing at North Avenue Beach. Whether you're looking just to gawk at some tricks or join a workshop, you can't beat the setting.

They offer workshops in skating, as well as orgainzed inline tours of the city. And if you're interested in making a bit of a statement about how you're rolling, get it on one of their critical mass events.

Bike Hikes

46. Bike Hikes

Location: Various (check website)
Website: forkandtheroad.com

Biking isn't just a way to save the planet and keep your ticker working all in one fell swoop, it's also a great way to see the city in a new way. No stranger to loving the bi-wheeled, Chicago offers gads of specialized tours by bike, including night tours and lakefront cruises.

They offer a number of specialized, one-time tours, including one based around doughnut spots in the city. So much for keeping heart healthy.

Brew & View

45. The Brew & View

Location: 3145 North Sheffield Ave.
Website: brewview.com

After dark, the Vic, a popular music venue, morphs into a movie house. A massive screen drops down in front of the stage, and movie-goers are encouraged to, well, sample some brews while they view. The venue concentrates on cult classics (as well as popular flicks no longer in wide release), so if you'd like to kick back in a casual, often chatty, environment with some cheap drinks and film faves, this is one stop you can't miss.

Green City Market in Lincoln Park

44. Green City Market in Lincoln Park

Location: 1790 North Clark St.
Website: greencitymarket.org

Since 1998, Green City Market has been committed to providing local, sustainable food to Chicago's city dwellers. Chicago has a number of other farmers markets, but this is the only one that operates year-round—from November to April you'll find the wares comfortably situated indoors. Whether you're in the market for heirloom tomatoes, a chef cooking demonstration, or a tasting series, this is the only stop you need.

Robust Coffee Lounge

43. Robust Coffee Lounge

Location: 6300 South Woodlawn Ave.
Website: robustcoffeelounge.com

Truly a hidden gem of a coffee shop, this lounge is a mere four blocks south of the University of Chicago campus, and yet remains unknown to many of the students. Seemingly in the middle of nowhere (between empty lots, in fact), this outpost of sleek, industrial décor is still a recent edition to Chicago's South Side. With the draw of fair trade coffee and soon-to-be-famous Belgian waffles, it won't stay secret for much longer.

(For other great college coffee shops, see Complex's list of the 50 Best in America.)

Chicago's Oldest House

42. Noble-Seymour-Crippen House (Chicago's Oldest House)

Location: 5622-24 N. Newark Ave.
Website: norwoodparkhistoricalsociety.org

The Clarke House (built in 1836) is commonly, but mistakenly, considered to be Chicago's oldest. The title actually goes to the Noble-Seymour-Crippen house of 1833. A Chicago landmark since 1988, the former farmhouse now serves as museum and community center.

In 2000, the house was added to the National Register of Historic Places. During the tour of the house, you can read from the diary of one of the young ladies who once lived there. In Chicago, historical tours make everyone a pervert and a detective.

Old Town School of Folk Music Concert Series

41. Old Town School of Folk Music Concert Series

Location: 909 West Armitage Ave.
Website: oldtownschool.org

The Old Town School has been a Chicago institution for over 50 years, offering music and dance classes galore—over 700 of them. They also offer some of the best folk, world, and roots music concerts in the city, which you can catch at either of their two locations—one of which is housed in an old art deco library.

We recommend their Tango classes. Cheek to cheek, hip to hip. A great way to get close for you and your lady.

Also, on September 3, Old Town will be celebrating Brazilian Independence Day with an evening of dance and music. Sexy swagger from South America. We're there.

Food Trucks

40. Food Trucks

Location: Various (check websites)
Website: gaztro-wagon.com; thesouthernmac.com; thewagyuwagon.com; 5411empanadas.com

Though Portland and Austin claim food truck supremacy, Chicago's mobile meals are nothing to sleep on. Offering unconventional alternatives to your standard, non-moving lunch joints, check out some of these delicious restaurants on wheels.

For instance, Gaztro-Wagon, called the best sandwich shop in the city by the Chicago Tribune, offers gourmet sandwiches like Wild Boar Belly with ancho chili sauce. The Southern Mac and Cheese Truck has a large menu full of exciting takes on the comfort food favorite, with combinations like blue cheese, bacon and mushroom, and truffle-infused white cheddar.

The menus at these places change frequently, so come with an open mind and an empty stomach.

Music Box Theatre

39. Music Box Theatre

Location: 3733 North Southport Ave.
Website: musicboxtheatre.com

Satisfy your craving for indie, foreign, cult, classic and horror flicks at this funky little venue, which dates back to 1929—and is apparently haunted by a ghost named “Whitey,” who managed the theater from opening night until 1977.

The theatre also puts on special events, like the upcoming screening of the ESPN doc Catching Hellabout the foul ball deflected by Chicagoan Steve Bartman in Game 6 of the 2003 NLCS. The screening will be accompanied by a panel discussion featuring director Alex Gibney, producer Gary Cohen, EPSN writer Wayne Drehs, and Chasing October documentary director Matt Liston.

Remy Bumppo

38. Remy Bumppo

Location: 3717 North Ravenswood Ave.
Website: remybumppo.org

Named after the founder's pet cat and dog, the award-winning Remy (cat) Bumppo (dog) theater aims to both stir the heart and make you think—all that in an environment more intimate than you'd find in the downtown theater district.

Their current season is explicitly political, with plays that draw on the Civil War and the Civil Rights Movement. Oh, and there's even a play about kidnapping the dog of conservative Senator. These people aren't afraid to step on some toes in the name of art (and civil disobedience).

Neo-futurists

37. Neo-futurists

Location: 5153 North Ashland Ave.
Website: neofuturists.org

The interactive, ever-changing program of the cult-hit Too Much Light Makes the Baby Go Blind is —believe it or not—currently the longest running production in Chicago. The cast will stage a baker's dozen of short, improvised comedy sketches all for the cost of….well, it depends on the roll of a die, so be prepared to throw caution to the wind.

The act attempts to capture 30 plays in 60 minutes, taking the performance to some outrageous and chaotic places. No real way to prepare yourself for this one. Just come.

Supernatural Chicago

36. Supernatural Chicago

Location: 3638 West 110th Street
Website: supernaturalchicago.com

One of the creepiest things to hit up on a Friday night happens at the basement Excalibur nightclub, where “necromancer” Neil Tobin regales audiences with tales of Chicago's paranormal. The locale itself is said to be haunted, having claimed the lives of some residents seeking shelter there during the devastating 1871 Chicago fire. Prepare to be freaked out—and get a psychic demonstration while you're at it.

Underground Dining

35. Underground Dining

Locations: Various (check websites)
Website: clandestinodining.org; xmarxchicago.com; valeriebolon.com

Underground dining has become the “to-do” thing these days, and Chicago doesn't skimp on the offerings. It's hard to find supper clubs when they're supposed to be a “secret,” but there's always a delicate balance of concealing and revealing—gotta get the customers in somehow, right? Here are just a few hidden gems to get your taste buds in gear.

These meals typically throw strangers together at massive tables for meals with courses ascending into the double digits. It sounds like serious stuff, but this isn't for snobs. Just folks that want to grub good and hard (the crew at X-marx Chicago call the photo section of their website the "porn" section, so you know their head is in the right place).

Underground Comedy

34. Underground Comedy

Location: 2100 West Belmont Ave
Website: chicagoundergroundcomedy.com

There's more to the “second city” than just the Second City comedy club. To break away from the well-trod path, head below ground: to get a break from the usual improve fare, this non-comedy club environment gives you the hard-to-master art of stand-up. Watch innovative craft-honing that changes it up every night with a new act.

Pullman Historic District

33. Pullman Historic District

Location: 11141 South Cottage Grove Ave.
Website: pullmanil.org

An official Chicago Landmark, the Pullman District is the origin of the Pullman Company and factory, made famous for its “Pullman Sleeping Car.” The entire community was built expressly to house the factory's many employees (how's that for service?), the first of its kind in the country. Today it makes for one of Chicago's most unique neighborhoods. Feast your eyes on the decadent Hotel Florence (equipped with original furniture), or amble along with one of the many available walking tours.

Ravinia (park, amphitheater)

32. Ravinia Park and Amphitheater

Location: 418 Sheridan Rd.
Website: ravinia.org

Ravinia park is a tree-filled, grassy expanse north of the city, perfect for a romantic picnic, whiling away the hours with a book, or catching some outdoor music. You'll find an eclectic mix of classical, chamber music, jazz, opera, country, blues, and rock music on the menu.

Lawn tickets are typically cheap, and you can't go wrong with the outdoor setting. Bring your girl for some pastoral necking.

Chicago Photography Center

31. Chicago Photography Center

Location: 3301 North Lincoln Ave.
Website: chicagophoto.org

Whether your interests are in a photography boot camp, an exhibition, or a lecture series accompanied by a little vino, you can find it at the Chicago Photography Center. This non-profit organization's facilities include a classroom space, a computer lab, darkrooms, a lighting studio and a gallery that exhibits student, instructor, and invited artist's work.

Recent exhibitions include powerful stuff like Iraqi Eyes, a comprehensive look at life in the war-torn country. Not everything is that heavy, though. Ryan Zoghlin's Mixing it Up, Historically featured techincally impressive surfing photography. CPC covers it all.

Fountain of Time (Washington Park)

30. Fountain of Time (Washington Park)

Location: 5900 South Cottage Grove Ave.

This massive monument to peace between the US and Great Britain shows masses of humanity passing before an austere and eerie Father Time. Situated at the western edge of the grassy expanse known as the Midway Plaisance, this sculpture is about as excellent a spot as it gets for your contemplating mortality on your lunch break.

Extreme gelato (Black Dog)

29. Black Dog

Location: 859 North Damen Ave.
Website: blackdogchicago.com

With off-the-wall flavors such as sesame fig chocolate chip and goat cheese cashew caramel, this gourmet gelato locale gives Italy a run for its money. And the whiskey gelato bar (yes, whiskey, plus gelato, on a stick) may be as close to paradise as you'll get in this life.

(For other great food 'n booze combos, check out this list of 20 Great Booze-Infused Foods from Across America.)

Extreme cupcakes (Sprinkles, e.g.)

28. Extreme Cupcakes

Location: Sprinkles (50 E Walton St.)
Flirty Cupcakes (Various Locations)
Website: sprinkles.com
flirtycupcakes.com

There's far more to extreme food in Chi-town than bottomless deep dish pizza. For starters, try some gourmet, knock-your-socks-off cupcakes. This ain't no kids party fare, friends, these are little bites of heaven. Featured on the Oprah Winfrey Show and the Food Network, head over to the aptly named Sprinkles Cupcakes for some ginger lemon or red velvet—and be prepared to wait in line for them. No better indicator of quality than a line.

If you're looking for something more mobile, keep tabs on Flirty Cupcakes—food truck gone dessert!—where the location changes are as plentiful as the flavors.

Morton Arboretum

27. Morton Arboretum

Location: 4100 Rte 53, Lisle, Ill.
Website: mortonarb.org

When you need to get away from it all, there's no better escape than to the suburb of Lisle, Ill., home to 1,700 acres of picturesque rest and relaxation. You can discover this rare and unique area just west of Chicago along innumerable footpaths and trails, or you can follow one of the paved roads through the park in your car. Unfortunately, you can't take your car through the hedge maze. That would be cheating.

The Pedway

26. The Pedway

Location: 108 North State St.
Website: cityofchicago.org

Yes, winter in Chicago is brutal—but the locals know a secret: go underground. Below the streets and away from the bitter wind is a subterranean maze of walkways that connect to numerous train stations, stores, skyscrapers, and office buildings. Linking 40 blocks, this underground city has been necessary for surviving the winter blues for 60 years. Spend enough time down here, and you might become convinced you're inhabiting some futuristic sci-fi world.

Pilsen Murals

25. Pilsen Murals

Location: Pilsen

Chicago's Pilsen neighborhood serves up much more than delicious Mexican fare, the area is a hub of colorful, community-painted murals—dozens of them—the first of which went up in 1976. Aside from their striking artistic merit, the murals are historically significant for their portrayals of politics, society, reform, and revolution. Put one fist up for the Chi.

Germantown

24. Germantown

Location: Germantown

Chicago's Lincoln Square neighborhood, unofficially known as Germantown, offers Oktoberfest all year round (although they do have an official beer-swilling bonanza every fall). Authentic German beer, brats, and refurbished cobblestone sidewalks will put you in the mood—maybe for a little polka. (We've been known to polka when not sober. And we've found this is the best time for polka, especially with those finely dressed beer maids.)

Printer's Row

23. Printer's Row

Location: Printer's Row

Aside from railroads, printing was one of the original industries Chicago was built on. Although the presses have long-stopped, South Dearborn Street is still home to condos and lofts, first-rate booksellers, cafes, and the history of the publishing industry captured in murals on the Franklin Building. Architecture buffs take note.

South Shore Cultural Center

22. South Shore Cultural Center

Location: 7059 South South Shore Dr.
Website: chicagoparkdistrict.com

A former country club and now official Chicago Landmark (since 2004), the building has been around over 100 years. The opulent site once housed ballrooms, a golf course, and horse stables, and now offers arts and recreational programs like including cooking, yoga, dance, and ceramics classes. That's basically a well-rounded man curriculum, and also a great way to put you close proximity to ladies that will notice your newfound well-roundedness while you take note of theirs. (Sorry, we can't shut off that part of our brain.)

Devon Avenue

21. Devon Avenue

Location: Devon Ave.

The thoroughfare known as the Desi Corridor houses Chicago's own “Little India,” which is a bit of a misnomer since it is one of the biggest and best-known Indian, Pakistani, and Bangladeshi communities in North America. Whether you're looking for curry or saris, you won't go hungry here.

Check out Hema’s Kitchen (2439 West Devon Ave.) and Tiffin (2536 West Devon Ave.) two of our favorite spots.

Uptown

20. Uptown

Location: Uptown

Former playground of prohibition-era mobsters (The Green Mill [4802 North Broadway St.], Al Capone's famous old haunt, is still considered Chicago's best place to catch some jazz), this North Side neighborhood enclave is now home to the city's densest population of Vietnamese and Korean food and culture. Get your Pho while getting your culture, too. Browsing this neighborhood offers some of Chicago's finest, oldest theaters, such as the Aragon, Riviera, and Uptown Theater.

Puptown in Margate Park

19. Puptown in Margate Park

Location: 4921 North Marine Dr.
Website: chicagoparkdistrict.com

16,000 square feet of doggone crazy fun? Located in Margate Park, this massive, fenced-in area has been appropriately dubbed “Puptown,” since on any day of the week you'll find it overrun with the full spectrum of our canine friends.

We probably don't need to fill you in on this, but women love dogs (the animals, not you after seven beers). Do we need to be more explicit?

Rockefeller Memorial Chapel

18. Rockefeller Memorial Chapel

Location: 5850 South Woodlawn Ave.
Website: rockefeller.uchicago.edu

Funded by John D. Rockefeller as his “Final Gift” to the University of Chicago, the chapel named after him is a stunning, gothic-inspired building sporting a 72-bell carillon, sculptures of Plato and Zoroaster, and a world-famous E. M. Skinner organ. Aside from the structure alone, visitors can enjoy temporary art exhibits, restorative yoga, and mindfulness meditation within this inspiring space.

Jay and Kanye recorded Watch the Throne in hotels; maybe you'll be struck by a few bars in this Chicago landmark.

Chicago Cultural Center

17. Chicago Cultural Center

Location: 78 East Washington St.
Website: explorechicago.org

Chicago's original public library, completed in 1897, is a monument to the neo-classical architecture of the 1893 World's Fair. Inside you'll find sumptuous marble, mosaics, brass and (at 38 feet) the largest Tiffany stained-glass dome in the world. Aside from these visual marvels, you'll also find exhibits, lectures, music, and theater.

Currently on exhibition are a series of hand-painted movie posters from Ghana. The weird art covers American, Bollywood, and other films, but with strange twists, as if they've been imported from Bizarro World. You've never seen Godzilla look like this (not without the help of serious hallucinogens, and maybe a severely Christian upbringing).

Ernest Hemingway Foundation

16. Ernest Hemingway Foundation

Location: 200 N Oak Park Ave., Oak Park, Ill.
Website: ehfop.org

Papa Hemingway is usually associated with Key West, Florida, where he resided for many years. Just outside of Chicago, however, you'll find his birthplace—and a museum to go with it.

The museum houses an excellent collection of artwork from the film adaptations of Hemingway's stories and novels, as well as over 2,300 books, articles, correspondence, photographs and pamphlets of Hemingway's.

The museum recently hosted a birthday celebration in Papa's honor, which included a lecture from Steve Paul, an expert on the celebrated writer.

NEO

15. NEO

Location: 2350 North Clark St.
Website: neo-chicago.com

Tucked behind a hidden door down a narrow alley, NEO is not only Chicago's oldest nightclub, it inspired Keanu Reeves's character's name in the Matrix movies. When you go, you'll see why. This club pumps goth, industrial, alternative, retro, electronic, house, new wave and everything in between, all set against a landscape of concrete, granite, mirrors, and lights. Be prepared to let loose and dance till dawn. Or till the machines come to take you away.

Cemeteries (Graceland, etc)

14. Chicago's Cemeteries

Location: Graceland (4001 North Clark St.)
Rosehill (5800 N Ravenswood Ave.)

Graveyards usually aren't high on the typical tourist's To-Do List, but Chicago does things differently. With cemeteries as compelling for their landscaping and tombstone masonry as they are for their historical significance, Chicago has a lot to offer. The two most famous are Graceland and Rosehill, each of which offers an impressive roster of those buried within: from civil war soldiers to such Chicago architects as Louis Henry Sullivan and Daniel Burnham.

Weird Tours Chicago

13. Weird Tours Chicago

Location: 63 West Ontario St.
Website: weirdchicago.com

“Ghosts, Gangsters, and Ghouls” – little wonder this company is said to offer the “strangest” tours in Chicago. Not for those who can't handle the off-beat and left-of-center, the Weird Chicago Tour is based the book Weird Illinois – and true to its namesake project, the tours combine history, mystery, and the absurd. Whether you have a penchant for “crimes and assassins” or “sex and the supernatural,” this is your stop.

Puppet Bike

12. Puppet Bike

Location: Location changes
Website: puppetbike.com

There's nothing that can bring a smile to your face like an unexpected encounter with the Puppet Bike. Beloved by Chicagoans old and young alike, this mobile Technicolor contraption was founded by resident Jason Trusty about eight years ago, and the master skills of the puppeteers leave even the big kids rolling on the floor with laughter. Who knew a crummy day at the grind could be erased by the disarming, if crackpot, philosophizing of a felt dog? But then again, we've always felt non-humans made the best philosophers. Which is why we're still waiting for the Biz Markie puppet to update Nietzsche's Beyond Good and Evil to include a chapter on beatboxing.

Museum of Holography

11. Museum of Holography

Location: 1134 West Washington Blvd.

Not your typical museum fare, you'll find the entire place dedicated to the sci-fi awesomeness that is the hologram and laser imaging. This, the last holography museum in the U.S., is a great way to indulge the guilty pleasures of a youth spent watching Fill-In-The-Blank (Star Trek, e.g.).

Banksy Murals

10. Banksy Murals

Location: W 16th St. & S Carpenter; W Randolph St. & S. Peoria St.

The reclusive and innovative street-artist Banksy's documentary, Exit Through the Gift Shop, debuted in Chicago. Appropriately enough, there have been some potential graffiti-sightings around town by the artist himself. On West 16th Street & South Carpenter, you'll find “you concrete me” painted (appropriately) on a wall of concrete, and an Untouchables-inspired piece situated on the corner of Randolph and Peoria.

Smart Museum of Art

9. Smart Museum of Art

Location: 5550 South Greenwood Ave.
Website: smartmuseum.uchicago.edu

If you've got a hunger for some art but are squeamish of the crowds at the downtown Art Institute, this little museum in Hyde Park gives you culture without sacrificing your piece of mind. You'll find an eclectic collection of works spanning more than 5,000 years, offering samples of Degas, Matisse, Rothko, Rodin, the old Masters, the Chicago Imagists, and more.

Baha'i Temple

8. Bahá'í Temple

Location: 100 Linden Ave. Wilmette, Ill.
Website: bahai.us

Practitioners of Bahá'í—independent religion founded over 100 years ago in Iran—only have 7 temples worldwide they can visit, one of which is just outside of Chicago in Wilmette. Completed in 1953, Chicago's Bahá'í Temple is a massive, dome-like structure impressive both for the detail of the building and the surrounding gardens and fountains.

Some famous practicioners of Bahá'í: Rainn Wilson (of The Office) and Tom Morey, the inventor of the Boogie Board.

Kuma's Corner

7. Kuma's Corner

Location: 2900 West Belmont Ave.
Website: kumascorner.com

If you want a killer burger like none other, then this is the place to be. You'll find everything from fried eggs, frizzled onions, avocado, and poached pears on these pretzel bun works of art, with the soundtrack to match: every concoction is named after a heavy metal artist, which is fitting considering that's the only thing on the stereo. If the music ain't your thing, you'll still never taste a better or more off-the-wall burger, and the locals know all too well: nearly every night of the week you'll find them waiting one or even two hours for a seat at this tiny destination, biding their time savoring something from the extensive beer list, or basking in the décor: artistic pin-ups, extending all the way to the bathroom.

Redhead Piano Bar

6. Redhead Piano Bar

Location: 16 West Ontario St.
Website: redheadpianobar.com

Aside from being the best piano bar in town—with décor invoking the classic nostalgia of old Hollywood, and bartenders who know how to pour—you'll also find another late-night phenomenon most Tuesdays. Hold out until 2 a.m., and the musicians from the Underground Wonder Bar pile into the Red Head to jam until dawn.

L” Tour

5. “L” Tour

Location: 17 East Monroe St.
Website: chicagohistory.org

There's little more authentic about Chicago than the “L” system, and no better way to take a tour of the city—if a tour is what you're looking for. You can avoid the busses, trolleys, and segways (yeah, we know; we're pissed too) by hopping aboard one of the elevated trains for a guided tour. Pick your neighborhood or pick your train line, and you'll see the city while traveling like the natives do.

The Loop Tour offers the most scenic views, so photographers take note.

Japanese Garden in Jackson Park

4. Japanese Garden in Jackson Park

Location: 6401 S Stony Island Ave.
Website: hydepark.org

Hidden behind Hyde Park's Museum of Science and Industry is a lush oasis where you can escape from just about anything—including Chicago itself. Located on the “Wooded Island,” and reachable only by footbridges, the Osaka Japanese Garden sports quiet pools, gardens, and a replica of the Phoenix temple near Kyoto. You'll think you've left more than just the Windy City.

Promontory Point

3. Promontory Point

Location: 5491 South Shore Dr.
Website: chicagoparkdistrict.com

The best view of Chicago won't come from the downtown heights of the Sears (now “Willis”) Tower, but rather from a half-circle of land jutting out into Lake Michigan, eight miles south. On warm spring and summer afternoons, you'll find it teeming with picnics, grills, and the leisurely arc of Frisbees against a stunning backdrop of the Chicago skyline. This open, grassy gem of the Hyde Park neighborhood is a true find—for those willing to avoid the touristy throngs at Millennium Park and Navy Pier, that is.

The Dunes

2. The Dunes

Location: 1100 North Mineral Springs Rd., Porter, Ind.
Website: indianadunes.com

Located 50 miles southeast of Chicago you'll find the Dunes. Heading to the Indiana Dunes State Park makes for an excellent fieldtrip from the Windy City, complete with miles of trails, lakefront beaches, marshes, an off-road bike trail, and tree graveyards. 1.25 hours away by car and 90 minutes by the Metra, this park is much more than sand.

Oz Park

1. Oz Park

Location: 2021 North Burling St.
Website: chicagoparkdistrict.com

Tucked away in the once run-down Lincoln Park neighborhood sits one of the lesser known of Chicago's many parks (all 550 of them). Named after L. Frank Baum (1856-1919), author of the iconic The Wonderful Wizard of Oz, the park is located only a few miles east of where Baum settled in 1891.

The 13-acre park is very family-friendly, but even the big kids can't help being awed by the massive, unearthly statues of Dorothy & Toto, the Tin Man, Scarecrow, and Cowardly Lion. If that's not a good enough reason to check it out, you'll also find footpaths, volleyball nets, and basketball hoops. Skip down the yellow brick road to get in a couple of runs.