Chicago city guide

Discover the best of the Windy City

Downtown Chicago’s iconic skyline is rightly the first image that comes to mind for many when the city is mentioned, but the U.S.’s third most populous city is so much more. That's not to say there isn't excellent food and fun to be had downtown, but Chicago's real beating heart is in its neighborhoods, and a complete visit should include a wider sampling of all the Windy City has to offer. 

Words by Matt Lynch

Serhii Chrucky/Alamy Stock Photo

Logan Square

With its tree-lined boulevards and historic homes, Logan Square retains its considerable charm, despite significant development in recent years. Just over six miles northwest of the downtown Loop, it arguably possesses the most dynamic dining scene in the city—one packed with chef-driven restaurants and boundary-pushing bars, particularly along Milwaukee Avenue.

Serhii Chrucky/Alamy Stock Photo

West Loop

Chicago's West Loop has very nearly shed its hardscrabble meatpacking past—the neighbourhood is now dotted with high rises and ambitious restaurant concepts. The 2012 opening of the Morgan CTA on the Green Line gave the area a public transit anchor, and an influx of high profile corporate tenants like Google has only accelerated its frenetic transformation.

Jannis Werner/Alamy Stock Photo

Hyde Park

Home to the prestigious University of Chicago, this South Side lakefront neighborhood offers rich history and a contemporary energy. Hyde Park boasts numerous architectural treasures —The Museum of Science and Industry is housed in one of the few remaining structures from the “White City” of the 1893 World's Columbian Exposition, and Frank Lloyd Wright’s Robie House reopened to the public in early 2019 after an $11 million renovation.

Fine dining restaurants

Courtesy Illinois Office of Tourism


(312) 733-1314, 1350 W Randolph St, Chicago, IL 60607, USA

After working in some of Chicago's most celebrated kitchens (Blackbird, Publican), chef couple David and Anna Posey struck out on their own with Elske in the West Loop in 2016. Their elegant, Danish-inspired cuisine became an immediate hit, and the $90 tasting menu, while certainly not a minor expense, represents one of the best fine-dining bargains in the city


Courtesy North Pond

North Pond

(773) 477-5845, 2610 N Cannon Dr, Chicago, IL 60614, USA

Bruce Sherman's tranquil and long-running love letter to farm-driven Midwestern cooking, located on the edge of a literal pond within Lincoln Park, sometimes flies under the radar. The fresh, thoughtful food however, keeps people coming back to North Pond, particularly for celebratory occasions—check no one has rented it out for a wedding on the night you're angling for a reservation. 


Galdones Photography

El Ideas

(312) 226-8144, 2419 W 14th St, Chicago, IL 60608, USA

Phillip Foss’ innovative Douglas Park restaurant feels more like a dinner party thrown by (incredibly culinarily gifted) friends than a Michelin-starred eatery. The tasting menu is playful and innovative, and the no corkage fee BYOB policy contributes to a festive atmosphere where guests are free to mingle about the open kitchen and chat with staff.

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Best restaurants for foodies

Jason Little

Fat Rice

(773) 661-9170, 2957 W Diversey Ave, Chicago, IL 60647, USA

Owners Abe Conlon and Adrienne Lo ran an underground supper club before bursting into the spotlight with Fat Rice, their bustling ode to the cuisine of Macau, where centuries of Portuguese colonial rule created an intermingling of European and Chinese influences. Try the namsake dish—jasmine rice with various meats, seafood and condiments (not pictured).

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Galdones Photography


(312) 888-3041, 1020 W Madison St, Chicago, IL 60607, USA

Chicago loves its pasta, and arguably no restaurant is doing it better right now than Monteverde. Top Chef alum and 2017 James Beard winner Sarah Grueneberg’s inaugural solo effort is a carb lovers dream, where patrons can eye their meticulously handcrafted pasta in production thanks to an angled mirror above the bar. 

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Jude Goergen

Mi Tocaya Antojeria

(872) 315-3947, 2800 W Logan Blvd, Chicago, IL 60647, USA

“Mi Tocaya” translates to “my namesake,” an appropriate starting point for Diana Devila's deeply personal and refined approach to Mexican cuisine in her colorful and convivial Logan Square hotspot, where small-plate antojitos (“little cravings”) are celebrated.

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Classic Chicago restaurants

Collin Pierson

Gene & Georgetti

(312) 527-3718, 500 N Franklin St, Chicago, IL 60654, USA

The Godfather of Chicago steakhouses, Gene & Georgetti has been serving impressive cuts of beef alongside Italian favorites since 1941—including to the numerous celebrities whose pictures adorn the walls. Dig into a plate of garlicky Shrimp DeJonghe before starting work on a juicy ribeye.

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Chicago Pizza & Oven Grinder

(773) 248-2570, 2121 N Clark St, Chicago, IL 60614, USA

There are many excellent local options for a deep dish experience, but Chicago Pizza & Oven Grinder offers something different—the pizza pot pie. This indulgent creation is cooked in a crust-covered ceramic bowl and then inverted onto the plate. If that’s not enough excitement for you, the restaurant sits across the street from the site of the 1929 St. Valentine's Day Massacre.

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Best bakeries and coffee shops

Mistey Nguyen

Cà Phê Dá

(773) 999-1800, 1/2, 1800 S Carpenter St, Chicago, IL 60608, United States

A more casual sibling to Thai and Danielle Dan’s Pilsen standout HaiSous, Cà Phê Dá’s lineup of specialty coffee drinks derives from the former’s family roasting operation in Vietnam—try the indulgent combination of coffee and vanilla egg custard. The coconut buns and lychee Danishes are equally impressive. 


Best Chicago cocktail bars

Clayton Hauck


(312) 600-0600, 660 W Lake St, Chicago, IL 60661, USA

It doesn't take a cocktail scholar to decipher the drinks menu at Moneygun—amaretto sour, Long Island iced tea, hurricane—but these familiar drinks are assembled with such care and craft that there's no question Moneygun is a serious cocktail bar masquerading as a hip, understated dive.

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Clayton Hauck

Lost Lake

(773) 293-6048, 3154 W Diversey Ave, Chicago, IL 60647, USA

Chicago cocktail legend Paul McGee’s Logan Square tiki bar is a rum-soaked hideaway serving thoughtfully recreated tropical classics alongside modern creations from the talented bar staff. The rest of the country has taken notice—Lost Lake was named Best American Cocktail Bar at 2018’s Tales of the Cocktail. 

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Where to drink craft beer

Courtesy Half Acre

Half Acre

(773) 754-8488, 2050 W Balmoral Ave, Chicago, IL 60625, USA

Lincoln Square’s Half Acre was one of the first true neighborhood craft breweries in Chicago and remains among its best loved—so much so there is now a second location a couple of miles north on Balmoral Ave. Fortunately, that pint of Daisy Cutter tastes equally bright and hoppy at either spot.

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Courtesy Revolution Brewing

Revolution Brewing

(773) 588-2267, 3340 N Kedzie Ave, Chicago, IL 60618, USA

Revolution’s original home, a Logan Square brewpub, still thrives, but demand necessitated more space. Imbibing at the more cavernous Avondale brewery is a different experience that caters better to hardcore beer geeks who get added value from enjoying their pints of Citra Hero alongside bourbon barrels that are aging next year’s release of Deth’s Tar imperial stout.


Best bars with a view

Courtesy J. Parker

The J. Parker

(312) 254-4747, 1816 N Clark St, Chicago, IL 60614, USA

Perched atop the Hotel Lincoln, The J. Parker’s location affords it an unobstructed view of the lakefront and a northerly perspective on Chicago’s iconic skyline. A retractable glass roof ensures it’s possible to enjoy said views even through the harsh local winters.

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Courtesy Drumbar


(312) 933-4805, 201 E Delaware Pl, Chicago, IL 60611, USA

Drumbar is a legitimate cocktail destination that just happens to have a stunning perch on the 18th floor of the Rafaello Hotel. The luxurious interior with plush leather couches and floor-to-ceiling windows gives way to a breezy outdoor terrace outfitted with fire pits to combat the chill.

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Kailley Lindman

I|O Godfrey

(312) 649-2000, 127 W Huron St, Chicago, IL 60654, USA

The Godfrey Hotel's sprawling indoor-outdoor rooftop party pad opened to considerable fanfare in 2017 and hasn't slowed. Sleek white couches and canopies create a more southerly vibe than Chicago in the summertime, and the outdoor fun doesn't stop in the winter thanks to transparent pop-up “igloos.”

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Historic Chicago hotels

The Drake/Hilton

The Drake

(312) 787-2200, 140 E Walton Pl, Chicago, IL 60611, USA

This stately Gold Coast hotel has hosted such dignitaries as Winston Churchill, Pope John Paul II and Princess Diana since opening in 1920. Afternoon tea at the Palm Court is an institution unto itself, and its position at the north end of Michigan Avenue is ideal for shopaholics.

Courtesy Palmer House Hilton

Palmer House Hilton

(312) 726-7500, 17 E Monroe St, Chicago, IL 60603, USA

The legendary Palmer House was already on its third iteration—the original opened a scant 13 days before succumbing to the Great Chicago fire and its successor was razed to make way for a larger facility—before Conrad Hilton purchased it in 1945. Legend has it the brownie was invented here during the 1893 World's Columbian Exposition.

Best luxury hotels

Courtesy The Langham

The Langham Chicago

(312) 923-9988, 330 N Wabash Ave, Chicago, IL 60611, USA

Chicago has plenty of luxury hotels, but The Langham is the only one situated in a building designed by legendary architect Mies van der Rohe, occupying floors two to 13 of the IBM Building on Wabash. The opulent interiors, top-notch wellness spa and riverfront views match its auspicious location.

Courtesy The Peninsula Chicago

The Peninsula Chicago

(312) 337-2888, 108 E Superior St, Chicago, IL 60611, USA

Opened in 2001, The Peninsula Chicago is designed in shades of off-white, with French-blue accents, hints of gleaming dark wood, and cream upholstery. Situated on the Magnificent Mile, the property has four dining options, including the Europe-centric Pierrot Gourmet and The Lobby restaurant with soaring ceilings and contemporary American fare. The 19th and 20th floors are dedicated to a spa, pool and fitness center with floor-to-ceiling windows.

Thomas Hart Shelby

Chicago Athletic Association hotel

(312) 940-3552, 12 S Michigan Ave, Chicago, IL 60603, USA

Reborn in 2015 after the renovation of a longtime private club of the same name, the Chicago Athletic Association hotel’s amenities speak to its athletic past, including an indoor bocce court in the gaming room just off the lobby. Don't miss a drink at Cindy's, a rooftop bar with some of the best views in the city.

Boutique hotels

Courtesy Kimpton Hotel Monaco

Kimpton Hotel Monaco

(312) 960-8500, 225 N Wabash Ave, Chicago, IL 60601, USA

Housed in a former riverside millinery in the northeast Loop, the Kimpton Hotel Monaco boasts an elegant design asethetic throughout its rooms and suites, stunning views, and a mussel and beer bar to lose hours in. You’ll even find a yoga mat under each bed to up the relaxation factor.

Joshua Haines

The Publishing House

(312) 554-5857, 108 N May St, Chicago, IL 60607, USA

This literary-themed bed and breakfast opened in 2017 in a building that once homed the Free Methodist Publishing House (and more recently the now-defunct Museum of Holography). The 11 stylish rooms, appropriately sporting names like “Bellow” and “Sinclair,” provide a unique experience in the red hot West Loop.

Must visit Chicago museums

Adam Alexander, Courtesy of the Illinois Office of Tourism

Art Institute of Chicago

(312) 443-3600, 111 S Michigan Ave, Chicago, IL 60603, USA

From the iconic bronze lion sculptures guarding the facade to iconic works like American Gothic, the Art Institute of Chicago has few peers among American art museums. Following the 2009 opening of the Renzo Piano-designed modern wing, only New York’s Metropolitan Museum of Art is larger.

Music and comedy

Dice Sales

Green Mill

(773) 878-5552, 4802 N Broadway, Chicago, IL 60640, USA

This legendary Uptown jazz club feels relatively unchanged from the days when it was a noted hangout of Al Capone, but don’t ask to see the secret escape tunnels underneath the bar. They don’t let anyone down there. Just enjoy the reliably excellent live jazz.


Courtesy The Second City

The Second City

(312) 337-3992, 1616 N Wells St, Chicago, IL 60614, USA

The list of comedy legends who’ve graced The Second City’s main stage is too long to get into—just note the endless photos of them performing to small crowds before they were household names, then catch a future star on stage at this comedy institution.

Clayton Hauck

Lincoln Hall

(773) 525-2501, 2424 N Lincoln Ave, Chicago, IL 60614, USA

This renovated former movie theater is known for booking talented musical acts of all types and having some of the finest sound quality in the city—the Lincoln Hall’s ownership group also runs longtime favorite Schuba’s Tavern, a fine venue in its own right.

Hiking and biking

Dice Sales

The 606

(312) 742-4622, Chicago, IL 60647, USA

Formally known as “The Bloomingdale Line,” Chicago's answer to New York City’s High Line took a defunct 2.7-mile stretch of railroad and converted it into an elevated, landscaped bike and pedestrian trail that links four Chicago neighborhoods—Wicker Park, Bucktown, Logan Square and Humboldt Park.

Dice Sales

Lakefront Trail

Lakefront Trail, Chicago, IL, USA

The 18-mile paved pathway that traces Chicago’s shoreline connects the North and South sides, links numerous parks and beaches, and provides the unmatched experience of having the endless expanse of Lake Michigan to one side and the towering skyline to the other.

Courtesy The Morton Arboretum

Morton Arboretum

(630) 968-0074, 4100 IL-53, Lisle, IL 60532, USA

Head to suburban Lisle for this 1,700 acre public garden founded in 1922 by Joy Morton, best known as the man who started Morton Salt. Today Morton Arboretum is home to more than 4,000 plant species and numerous tranquil trails for hiking and biking.

Shopping in Chicago

Adam Alexander

The Magnificent Mile

Magnificent Mile, Chicago, IL 60611, USA

If you only know a few areas of Chicago, The Magnificent Mile is likely one of them, but that doesn't make the collection of luxury retail any less impressive, not to mention the opportunity to take in architectural treasures like Tribune Tower and the Wrigley Building in between stores.

Courtesy Illinois Office of Tourism

Wicker Park/Bucktown

Wicker Park, Chicago, IL, USA

These adjacent, eminently walkable neighborhoods may have lost a bit of the hipster edge that defined them in the early aughts, but they still represent a more eclectic shopping experience to the more staid Magnificent Mile, with a combination of independent boutiques and chain retail, plus a diverse array of dining options.

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