Chicago City Guide

A rough and tumble, working class town that exudes no shortage of glitz, the culture-rich “City of (the) Big Shoulders” is defined by its neighborhoods — a dizzying number of communities with fluid boundaries, each boasting its own unique feel and, often, cultural heritage.      

This includes Chicago’s Little Italy, Chinatown, Greektown, noodle shop-lined Argyle Street and kaleidoscopic “Little India” along Devon Avenue. From Pilsen’s Latinx community to Hyde Park’s thriving Black community; Swedish-inflected Andersonville; German vestiges in Lincoln Square; “Polish Downtown”; and Paseo Boricua — the nation’s only officially recognized Puerto Rican neighborhood — there’s so much waiting to be explored.     

Whether you dig dining on small plates from James Beard Award-winning chefs, favor exemplary architecture or want to while away the day at museums, Chicago offers so much more than its breathtaking lake and skyline views.

Immerse yourself in what Chicago locals know with Mayflower’s Chicago City Guide.

Where to Get a Culture Fix in Chicago

Chicago is stereotyped as a brawny, broad-shouldered place — the kind where people say “tree” instead of “three.” In reality, though, Chicago is a sophisticated, richly cultured place filled with fascinating performance venues, galleries and noteworthy museums of every type.     
Known for inventing or advancing myriad performing arts, Chicago’s cultural legacy extends to improv comedy; architecture; literature; and the visual arts. As for its museums, well, they’ve earned their rightful place on the world stage.    

Not to be forgotten is Chicago’s literary history. It’s here that poets like Gwendolyn Brooks and Carl Sandburg came to prominence and writers from Ernest Hemingway to Saul Bellow and Upton Sinclair lived and/or honed their skills. Although narrowing down the options can be daunting, these enriching, inspiring locales are the perfect place to get a culture fix.    

Spend a day at Chicago’s Museum Campus, a 57-acre lakefront park adjacent to Northerly Island. Here, you’ll find five of the city’s most notable attractions: the Adler Planetarium, America’s first; the Shedd Aquarium; the Field Museum, its origins traced to the 1893 World’s Columbian Exposition; Soldier Field, home of the Chicago Bears; and the Lakeside Center of McCormick Place, an exhibition space.    

Escape the cold — or simply the outside world — at the stunning Garfield Park Conservatory. This lush, 10-acre botanical landscape-under-glass is a year-round destination, with indoor display gardens that reveal a variety of habitats.    

Located in the West Town neighborhood, Intuit: The Center for Intuitive and Outsider Art showcases the work of artists who demonstrate little influence from the mainstream art world. The result? Uniquely expressive, thought-provoking work that’s beyond worth your time.    

Purportedly haunted, the Music Box Theatre is not for Hollywood blockbuster-seekers. Rather, the two-screen cinema shows the latest independent films and documentaries, with midnight screenings of cult classics, all beneath a ceiling of gently twinkling, starlit “skies.”    

The oldest outdoor musical festival in the United States, Ravinia Festival is also one of the most beautiful venues around. Spread a picnic blanket beneath its old-growth trees, enjoy a BYOB meal that’s as gourmet as you dare to prepare, and take in live symphony performances, as well as nationally recognized artists.    

The Chicago Arts District hosts 2nd Fridays Gallery Night, when galleries and artists’ studios from 1711 to 2005 South Halsted Street open their doors for viewing free of charge.     

Millennium Park’s Jay Pritzker Pavilion hosts a dizzying array of cultural events, including the Summer Music and Film Series; gospel, jazz, blues, mariachi and world music festivals; performances by the Chicago Jazz Philharmonic; Broadway in Chicago; the Lyric Opera and Grant Park Music Festival; and NPR’s Wait, Wait, Don’t Tell Me. Nearby, you’ll also find impressive outdoor art, arguably the most famous of which is Cloud Gate (a.k.a. “The Bean,” 201 E. Randolph St.). It’s also the site of the interactive Crown Fountain. Not to be overlooked, the park also houses the al fresco Boeing Galleries at its north and south reaches.    
Looking for something more immersive? Chicago’s neighborhood museums reveal the rich fabric of Chicago’s immigrant population and the role the diaspora has played in the world at large. Start your explorations at DuSable Museum of African American History, The Polish Museum of America, the Swedish American Museum, the National Museum of Puerto Rican Arts & Culture, and the Ukrainian Institute of Modern Art. Continue onward, perhaps, to the Chinese-American Museum of Chicago and Heritage Museum of Asian Art, both of which are located in Chinatown. Meanwhile, the National Hellenic Museum in Greektown contains 17,000 artifacts that span thousands of years and Pilsen’s National Museum of Mexican Art houses a collection of more than 10,000 works, making it one of the largest in the country. 

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Things You Can Only See and Experience in Chicago

Chicago is a definitive city. The birthplace of the Ferris Wheel, mobile phones, zippers and even farm silos, the list of Chicago originals goes on. Want to live like a local? There are a few interesting — and unquestionably quirky — things you should know.    

Used to your pizza getting cut into wedges? Get hip to the “party cut.” Chicago’s grid-style slices are ubiquitous and have since been popularized around the Midwest.     

As you traverse the city, keep watch for the Puppet Bike, a traveling puppet show featuring characters that dance to oldies beneath a disco ball. The bike — a fully mobile stage — is most seen on the streets of the Andersonville, as well as in The Loop.   

Jeppson’s Malört — once you’ve had it, you’ll never forget. Known for its bitter (that’s an understatement) taste, this Swedish-style liqueur comes courtesy of the Carl Jeppson Company, founded in Chicago in the 1930s. Flavored with wormwood, you’ll find it at neighborhood taverns. Check out the company’s unaired commercial for a good laugh.      

Chicago was once the capital of filmmaking, years before film studios appeared on the West Coast. In fact, in the early 1900s, Chicago housed more film studios and production companies than any other city. The largest at the time was Essanay Studios, which kick-started Charlie Chaplin’s career.    

The Tamale Guy (a.k.a. Claudio Velez) carved out a unique niche when he’d show up at bars late at night, holding a red or blue cooler loaded with pork, cheese, or chicken tamales. You can also follow him via the Tamale Tracker or head to his brick-and-mortar restaurant, Tamale Guy Chicago

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Where to Get Outdoors in Chicago

Make the most of Chicago’s warm, sunny weather, whether your workout routine involves easy strolls, watersports or pedaling along the lakefront. Intersected by trails and bike routes, there is also green space galore.    

The Chicago Park District operates more than 8,800 acres of green space, making it the largest municipal park manager in the nation. In fact, 99.6% of Chicago residents are within a 10-minute walk of a park. So, yes, there’s an outdoor activity to suit every manner of outdoor enthusiast. Here are a few that should not be missed.     

Everyone — for good reason — knows about the scenic Chicago Riverwalk and 18.5-mile Chicago Lakefront Trail. For a more local experience, however, those in-the-know head to the 606, a 2.7-mile urban hiking trail elevated 17 feet above four of the city’s hippest neighborhoods. Running east-west along an abandoned railway, it extends from the Bloomingdale Trail, between Ashland  and Ridgeway  on the northwest side of Chicago.    
When you’re tired of the trails more traveled, though, consider these memorable walks. They’re urban oases right within city limits.   

Tucked behind Soldier Field, the Shedd Aquarium and McCormick Place is Northerly Island, a hidden treasure originally built for the 1933 World’s Fair. The former home of city airport Meigs Field — infamously bulldozed overnight by Mayor Richard M. Daley — today, the 91-acre man-made peninsula hosts summer concerts from major artists. Its real draw, though? The picturesque walking paths and panoramic skyline view.     

Starting in Gompers Park at Foster and Kostner Avenues on the city’s Northwest Side, the fully paved, mixed-use North Branch Trail skirts the north branch of the Chicago River, snaking 22 miles up through the LaBagh Woods and the Skokie Lagoons to the Chicago Botanic Garden in Glencoe. From there, it links to the Green Bay Trail, continuing up the North Shore.    

Historic, 337-acre Washington Park boasts plenty of beautiful paths for walking and running. It’s also the site of Lorado Taft’s famed Fountain of Time sculpture. Designed by Frederick Law Olmsted and Calvert Vaux, the park’s scenic landscape and tranquil lagoon give way to nearby, 500-acre Jackson Park, site of the 1893 World’s Columbian Exposition. Venture a bit further for a stroll through the University of Chicago campus.    

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Local Eats in Chicago

A culinary mecca, Chicago was ranked as the number one city in the world for both eating and drinking, according to the Time Out Index, which polled more than 34,000 people in 48 cities around the globe. It was also recently named “Best Restaurant City” by Bon Appétit. From the West Loop to River North and Logan Square, strip mall one-offs to Alinea’s hallowed walls, you won’t find a city more suited to savoring. Following are a few of our favorite ways to indulge.    

You’re not a true Chicagoan until you experience one of the city’s “slashies.”  These liquor stores with attached “taprooms,” “packaged goods stores” or even restaurants attached are a late-night rite of passage. Where to start? Whet your whistle at Albany Park’s Marie’s Pizza & Liquors, where you can pick out a bottle or six-pack in front to enjoy with cracker-thin crust pies in back.    

If you have just one Chicago-style hot dog, make it the exemplary one at Gene & Jude’s. Around since, well, forever, its buns are perfectly steamed, its dogs properly snappy, and its pitch-perfect toppings a mélange of mustard, onions, sport peppers and relish, finished with a pile of fries.     

Mind you, Chicago invented — or perfected — about a zillion foods we hold near and dear. This includes the Twinkie and Wrigley’s Spearmint and Doublemint Gum. From pizza puffs — a mainstay at Chicago’s fast-food stands — to flaming saganaki and gyros, both Greektown staples, Chicago’s culinary history runs deep. Whether you’re a lifelong Chicagoan or just getting acclimated to your new neighborhood, take time to seek out its lesser-known Chicago originals, too, like these.    

  • The Mother-in-Law consists of a tamale in a hotdog bun, cloaked in chili and finished with the fixings of a traditional, Chicago-style dog. It’s joined by the Humdinger, a Mother-in-Law sandwich topped with melted cheese. Get yours at Fat Johnnie’s Famous Red Hots, an off-the-beaten-path hot dog shack in Marquette Park.    
  • The Big Baby is a cheesy, double-decker burger slathered with grilled onions — and it’s calling your name at Bronzeville’s Southtown Sub.   
  • Get a gut-bomb breaded steak sandwich from Ricobene’s. Blanketed in tomato sauce and cheese, it’s a South Side staple.    
  • For a twist on the traditional sandwich, try a Puerto Rican jibarito at Borinquen Lounge in Humboldt Park. Instead of bread, planks of flat, crispy, fried plantains cradle seared steak (or another protein), along with mayonnaise, melted American cheese and a generous slather of garlic oil.    
  • The Jim Shoe is an unholy mess of a sandwich bursting with roast and corned beef, gyro meat, lettuce, tomato, mustard, mayo, tzatziki and cheese. If you only try one, make it the version from Southtown Sub.   
  • The Maxwell Street Polish is a garlicky, smoky, snappy, deep-fried polish dog that’s tucked into a bun and topped with yellow mustard, grilled onions and sport peppers. Its birthplace? The original Maxwell Street Market, an open-air flea market that was  established in the late 1800s. Get this original grub 24/7 at Jim’s Original in University Village.     
  • The Freddy is an Italian sausage patty that’s cloaked in bubbly mozzarella cheese, marinara sauce and peppers served atop a French roll. Try the standout rendition at Italian market and deli Calabria Imports.   
  • Fried, lollipop-style Gam Pong chicken wings, tossed in a fiery-sweet sauce, appeared in the mid-1980s in the Albany Park neighborhood. That tradition lives on at Chinese spot Great Sea Restaurant.  

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Locally Loved Chicago Coffee Shops

Few things help you hit the ground running like a good, roasty cup of coffee. Fortunately, Chicago has its fair share of notable beaneries.    

These days, Metropolis Coffee Company is a mostly wholesale business in Avondale, though it all began at this Edgewater café, a welcoming joint where neighborhood types chill with their laptops or a book or gather with friends.     

Experience the world without leaving town at Oromo Cafe, where baristas create unique coffee drinks that combine global beans and flavors and ingredients, such as superfoods, serving them alongside sandwiches, pastries, and other treats. There is a location in Bucktown as well.   

Gaslight Coffee Roasters regularly rotates its selection of house-roasted coffees, drawing a crowd of hipsters and neighborhood families to its small, adjacent Logan Square café.    

Tucked between Bustling Milwaukee Avenue and the populated 606, Ipento 606 is a lively place for a cayenne-laced latte and piping-hot house-made donut.   

Spoiler alert: The Wormhole Coffee features a serious throwback focal point — Marty McFly’s Delorean cozy Wicker Park space for notable drink specials. Wormhole 2 is located in the Bucktown/Logan Square neighborhood. The daily drink specials on the menu are what makes this coffee house stand out.   

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Chicago Nightlife Happy Hour Haunts and Nightlife

Chicago’s nightlife scene is no slouch. You’ll find everything from late-night dance floors to intimate lounges, storied comedy clubs and legendary music venues. Speakeasies, sultry music venues, nationally lauded breweries and culinary cocktail experiences abound, too.    

From its proliferation of nationally recognized breweries to its craft distilleries, cocktail bars, speakeasies, dives and clubs, Chicago’s nightlife scene is lively. Carrying into the wee hours, the state doesn’t have a set bar closing time. Meanwhile, most counties allow liquor sales until 2 a.m. In Chicago, though, bars with late night licenses sell until 4 a.m. Sunday through Friday, and until 5 a.m. Saturday. Fortunately, there are plenty of around-the-clock diners and dives to temper overindulgence.    

Not sure where to start? Try working your way through these beloved sipping spots.   

Known for its excellent live jazz, performed by legendary musicians, Uptown’s Green Mill Cocktail Lounge keeps alive the sounds of the early ’30s and ’40s. On Sundays, it’s also the site of the internationally acclaimed Uptown Poetry Slam. While here, be sure to check out Al Capone’s favorite booth, which offered unobstructed views of the bar’s entrances. There is also an access hatch to the city’s erstwhile, underground tunnels. Located behind the long end of the bar, the secret entrance discreetly connects the venue to an adjacent building.    

As sophisticated as the day is long, The Violet Hour serves artisanal, seasonally driven libations in a refined, Instagram-worthy Wicker Park space.     

Consider Paul Kahan’s honky-tonk, bourbon and beer-centric Big Star your go-to for chef-driven Mexican street food. Set in a former 1940s gas station in Wicker Park, there are few better to while away a summer afternoon. Grab a seat on its popular, sun-drenched patio, clutching a cilantro-showered, grilled pineapple-dotted al pastor taco in hand. There is a second outpost in Wrigleyville.   

Punk rock and whiskey go hand-in-hand at Delilah’s, a Lincoln Park hole-in-the-wall that attracts an eclectic crowd — from DePaul coeds to tatted-up indie rockers — who commingle over its killer jukebox, over-the-top whiskey selection, 300-bottle-strong beer list, and arcade games that help pass the time between rounds.   

Sip tiki drinks — some flaming — at Three Dots and a Dash  in River North. Beyond its 200-plus selection of rum, the Polynesian lounge dishes up hangover-abating, luau-inspired bites, like coconut shrimp and “island fries” topped with pulled pork. A lounge-within-a-lounge, sibling The Bamboo Room turns out refined rum cocktails from a local cocktail expert.   

The most intimate cocktail experience around, eight-seat microbar Milk Room is tucked into the second floor of The Chicago Athletic Association. Used as a speakeasy during Prohibition, its cocktails are crafted with rare vintage spirits and elixirs.   

Expect live honky-tonk tunes, line dancing and karaoke at Carol’s Pub, a late-night institution dating back to 1973. A shot and a beer kind of joint, it offers a no-nonsense grub, like a fried bologna sandwich.   

There are plenty of excellent microbreweries in Chicago. Logan Square’s Revolution Brewing is certainly one of them. Here, though, the food garners almost as much attention as the beer. Whether you settle on Fist City-battered cheese curds with Calabrian chili aioli; applewood-smoked wings; or the griddled cheeseburger with beer-spiked secret sauce, griddled onions, lettuce and locally grown tomatoes, wash it down with an Anti-Hero IPA.   

If it’s a low-key indie vibe that you seek, look no further than Maria’s Packaged Goods and Community Bar in the Bridgeport neighborhood. The brainchild of Lumpen’s editor-publisher, Ed Marszewski, and his brother, Mike, the artsy watering hole is tucked into the former home of Kaplan’s Liquors, a bar that was owned and operated by their mother, Maria, since the mid-’80s. Low-lit from bottle-chandeliers, the hybrid liquor-store-lounge (a.k.a. “slashie”) offers 300-plus microbrews, likeable cocktails and Korean-Polish fusion from sib Kimski.  

Seemingly unchanged since it opened in the 1930’s, 4 a.m. Wicker Park dive bar Rainbo Club is where Liz Phair snapped her album cover photo for Exile in Guyville. A local favorite after all these years, you’ll find a cross section of revelers, who come for live acts and cheap drafts, poured from behind the shamrock-shaped bar. Grab a red vinyl booth if you can. Then, keep your eyes trained on the intimate, dimly lit space since respected artists drop by for the occasional word-of-mouth performance.   

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Hidden Gems in Chicago

Filled with fascinating and unusual landmarks and experiences, Chicago’s most beloved nooks feel like a best-kept secret. When you’re looking for something new to do, go off the beaten path to discover these special, though lesser-known, locales.   

Tucked off of bustling Fullerton Parkway adjacent to Lincoln Park, the Alfred Caldwell Lily Pool, a tranquil, Prairie-style respite designed by landscape architect Alfred Caldwell.  

Take a water taxi to Chinatown from the Chicago Riverwalk to explore the lively scene at Cermak Road and Wentworth Avenue. After pursuing the tchotchke-filled shops, pop into a teahouse, grab Chinese delicacies from a local market or sit down to dim sum. Then, perhaps visit Ping Tom Memorial Park, a 17-acre, riverside site with a boathouse, kayak rentals and walking paths —  not to mention an impressive pagoda.    

Whimsical Oz Park was named in honor of author L. Frank Baum, who lived in the area in the 1890s. In the spirit of the Wizard of Oz, its playground (“Dorothy’s Playlot”) gives way to a green space called Emerald Gardens. Strolling onward, spot the Tin Man, Scarecrow, Cowardly Lion, Dorothy and Toto, created by local artist John Kearney.    

You can assemble your own masterpiece at The Chicago Mosaic School. With a comprehensive lineup of over 150 classes and workshops helmed by mosaic masters, there’s something for enthusiasts and artists alike.    

Chicago’s Hermosa neighborhood is home to the Walt Disney Birthplace, a simple worker’s cottage built by his parents in 1893. Although it’s currently under restoration, you can still snap a quick selfie outside.  

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Getting Around in Chicago

Unlike a lot of major U.S. cities, navigating Chicago is relatively easy, thanks to its grid system, starting at Madison 0 north/south and State Street east/west and radiating outward N, S, E, and W from there. Think of it in terms of mathematics — coordinates are found based on an X and Y axis. In other words, X equals north and south addresses, while Y equals addresses that are east and west.

Mass Transit 

Mass transit in the Windy City is a major amenity. The Chicago Transit Authority (CTA) operates eight elevated “L” train lines and nearly 130 bus routes. Different fare structures are in place; however, Ventra, an electronic fare payment system, is used throughout the system. 


Featured in countless movies and TV shows, the “L” is probably one of the most iconic symbols of Chicago. Here’s a rundown of the various lines and services: 

  • The Red Line provides 24-hour service between the North and South Sides via downtown 
  • The Blue Line connects O’Hare International Airport and downtown 
  • The Brown Line operates between Kimball and downtown 
  • The Green Line provides service between suburban Forest Park and 63rd Street on Chicago’s South Side 
  • The Orange Line provides service between Midway Airport, the Loop and Chicago’s Southwest Side 
  • The Purple Line provides service between Linden (in Wilmette) and Howard (in Chicago) via Evanston 
  • The Pink Line provides service from 54th/Cermak (in suburban Cicero) to The Loop 
  • The Yellow Line provides service between Dempster-Skokie (in suburban Skokie) and Howard (in Chicago), with connecting service to downtown Chicago


In addition to the city buses operated by CTA, suburban travelers and commuters can use longer distance PACE lines, which accept the Ventra card. 


Need a carpool buddy? Try ridesharing


While it’s possible to hail a cab in more densely populated neighborhoods, the city’s CHICABS program lets passengers e-hail and pay fares via approved mobile apps, including ARRO and CURB. One of the more popular “traditional” cab companies is Checker Taxi. 

Water Taxi 

Whether it’s to explore or get around town, consider hopping aboard a water taxi, which connects several neighborhoods. 

Shuttles and Limos

Airport shuttles offer a convenient alternative when traveling to and from O’Hare. Go Airport Express is a popular choice. For a limousine, check out Elite or Echo. 


With an extensive network of designated lanes and generally flat terrain, bicycling is becoming a mainstream mode of transportation for active Chicagoans. Bike -sharing is also on the rise, with Divvy serving as the city’s official bike share system.

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Looking for more ways to immerse yourself in Chicago or others states and cities? Be sure to check out our blog for ideas that will help you settle in and start feeling like a local.  

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