Insider Guide: Best of Chicago

Insider Guide: Best of Chicago

From the restaurant where the Obamas eat to the clubs that make America laugh, welcome to the biggest small town in the States
If Buckingham Fountain's good enough to open an episode of "Married... With Children," it's good enough to open our expert guide to Chicago.

Ask anyone on the street what he or she likes most about Chicago, and you’ll mostly likely get “the friendly people.”

But what makes Chicagoans so gosh darn friendly?

Perhaps it’s the camaraderie they form during the city’s harsh winters and blessed summers.

Or maybe it’s because this Midwestern mecca has some of the best museums, restaurants and architecture in the world -- and it’s all actually affordable.

Whatever the reason, there’s nothing “second” about the Second City in the hearts of its citizens -- as well as most anyone else who’s explored this paradoxically folksy metropolis.

Print and go -- Our traveler-friendly one-page guide here: Best of Chicago



Dislike him or hate him, Donald Trump knows hotels. Trump Hotel

Donald Trump might be a walking caricature, but there are still some things that the billionaire real estate magnate does right, like constructing the second tallest building in Chicago (and the country, after the Willis Tower) with the best views of the city.

Even Pulitzer Prize-winning architecture critic Blair Kamin admitted the River North vistas from Trump’s four-star restaurant Sixteen -- when compared to the Signature Room on the 95th floor of the Hancock Center -- are “more intimate, practically putting you eyeball-to-eyeball with the Wrigley Building's clock tower and the flying buttresses of Tribune Tower.”

If you head down to the sleek 6,000-square-foot spa, expect a monster bill. A 90-minute facial, for example, will set you back $420 including tip, but that’s the price you pay when you want to live like the Donald.

Trump International Hotel & Tower Chicago, 401 N. Wabash Avenue, Chicago, IL 60611; +1 312 588 8000; from$395 per night

The King, or standard, Room. Waldorf Astoria

Last year Travel + Leisure ranked the Waldorf Astoria (formerly the Elysian) the top large-city hotel in the United States, and it’s easy to see why: the lobby’s glistening marble and starburst chandeliers rival the grandest beaux-arts hotels in Paris.

The 34-seat Bernard’s Bar on the second floor serves an excellent $14 champagne cocktail, and the classic Coco Chanel vibe is worth the price tag.

If you forgot to pack your Chanel or Savile Row suits for the occasion, you can pick up appropriate attire at one of the spendy shops on Oak Street, just around the corner.

Waldorf Astoria Chicago, 11 East Walton, Chicago, IL 60611; +1 312 646 1300; from $369 per night

The Grand Deluxe Suite, overlooking Michigan Avenue. The Peninsula

Another top-ranked U.S. hotel, the Peninsula offers the amenities that one expects from a five-star spot, including an indoor pool worthy of an F. Scott Fitzgerald novel, afternoon tea service that surpasses the high tea at London’s Savoy Hotel and a prime location in the center of the Magnificent Mile shopping district.

The spa services here are worth the price. In 2012, Chicago magazine ranked it one of the top day spas in the city, where the massages (around $165 per hour) blew away the competition.

The Peninsula Chicago, 108 East Superior Street at North Michigan Avenue, Chicago, IL 60611; +1 312 337 2888; from $395 per night


Public's concept is sophisticated accommodations and service at an affordable price. The Public

Unlike New York and Los Angeles, luxury hotels in downtown Chicago are generally cheaper (if not cheap), which means that mid-range rooms are even more of a bargain.

Built in 1926, the Ambassador East Hotel and its legendary Pump Room entertained the likes of Frank Sinatra and Judy Garland until it faded from the limelight. Then in 2010, hotel developer (and Studio 54 cofounder) Ian Schrager bought the building and poured $35 million into its renovation.

Renamed the Public, the Gold Coast hotel has quickly reclaimed its throne as the home away from home for the rich and beautiful -- many of whom like to cluster around the white couches of the Library bar before heading to the revamped Pump Room.

PUBLIC Chicago, 1301 North State Parkway, Chicago, IL 60610; +1 312 787 3700; from $180 per night

One of the few buildings to survive the Great Fire ... was demolished to make way for this building in 1895. Burnham Hotel

Recognize the name Burnham? That’s Daniel Burnham, the legendary architect, city planner and protagonist in Erik Larson’s bestseller Devil in the White City. Burnham’s firm also had a hand in designing the historic Reliance Building, which houses the Hotel Burnham in the Loop.

Completed in 1895, the Reliance Building is noteworthy for its floor-to-ceiling plate glass windows, a groundbreaking concept at the time. The interiors are a time warp, too, with elaborate metal elevator grilles, restored mosaic tile floors and tasteful touches of art nouveau splendor.

Hotel Burnham - a Kimpton Hotel, 1 W Washington St, Chicago, IL 60602; +1 312 782 1111; from $159 per night


Room 13 (of six). Don't ask. Inn at Longman & Eagle

In the past five years, the Logan Square neighborhood in Northwest Chicago has exploded as a hot bed for affluent hipsters -- Longman & Eagle is the epicenter.

The inn has only six rooms, all outfitted with classy-but-kitchy design elements ripped from the pages of Wallpaper magazine (or perhaps inspired by the Portland chic of the Ace Hotel chain).

The best part of staying at the inn is a guaranteed spot at the restaurant downstairs. The Michelin-rated gastropub doesn’t take reservations otherwise, and the wait can be up to two hours at peak times. 

Longman & Eagle, 2657 N. Kedzie Avenue, Chicago, IL 60647; +1 773 276 7110; from $85 per night


Hot Potato Cold Potato, one of Alinea's beloved forays into molecular gastronomy. Alinea

Until last year Alinea was the top American restaurant on the World’s 50 Best Restaurants list. Although it now ranks just below New York’s Per Se, no critic will argue chef Grant Achatz’s culinary inventiveness and striking presentation.

The always-evolving multi-course tasting menu comes out of the kitchen in a series of deconstructed bites served on everything from driftwood to lavender-scented pillows.

For his classic chocolate finale, Achatz or one of his crew serves the dessert right on the table, brushing and flicking ingredients with Jackson Pollock fervor.

The only downside is that Alinea has switched to a ticketed system for reservations. If you want a day-of table, keep tabs on Alinea’s Facebook page or Twitter feed for last-minute openings.

Alinea, 1723 North Halsted St., Chicago, IL 60614-5501; +1 312 867 0110; Wednesday-Sunday: 5 p.m.-6:30 p.m. and 8 p.m.-9:30 p.m; expensive

Jackets required for gentlemen. Spiaggia

When the Obamas are home in Chicago, there’s a chance you’ll see them dining at Chicago’s only four-star Italian restaurant. For nearly 30 years, the President’s favorite chef, Tony Mantuano, has served handmade pastas and wood-roasted proteins.

The scallops are another Obama favorite.

If the $175 truffle tasting menu at Spiaggia is beyond reach, Café Spiaggia next door offers an excellent introduction to Mantuano’s talents without breaking the bank.

Pastas, pizzas, and main dishes range from $14 to $58.

Spiaggia, 980 N Michigan Ave Level 2, Chicago, IL 60611; +1 312 280 2750; open daily: 11:30 a.m.-1:30 p.m., Sunday-Thursday: 6-10 p.m. and Friday-Saturday: 5:30-11 p.m.; expensive

Flavorful flautas from Frontera. Frontera Grill

Although the décor at Rick Bayless’s flagship restaurant is a bit dated, the food isn’t.

His modern twists on fresh Mexican cuisine -- crisp and bright ceviches, smoky salads, seasonal margaritas -- continue to please the guests who flood Frontera’s doors.

When the wait at Frontera Grill or Topolobampo (his more upscale restaurant next door) becomes unbearable, try Bayless’s casual spot, Xoco, on the corner. The service there is quicker and the famous tortas can be wrapped up to go.

Frontera Grill, 445 North Clark Street, Chicago, IL 60610; +1 312 661 1434; Tuesday-Friday: 11:30 a.m.-2:30 p.m., Saturday: 10:30 a.m.-2 p.m. (brunch), Tuesday: 5:30-10 p.m., Wednesday-Thursday: 5-11 p.m., Friday-Saturday: 5-11 p.m.; moderate

Modern Asian barbecue. BellyQ

If New York has Momofuku and David Chang, then Chicago has Bill Kim and his trio of modern Asian restaurants. Kim’s newest addition is BellyQ, a more upscale interpretation of his street fare made possible through a partnership with none other than Michael Jordan.

Here, the standouts are the tabletop barbecue (banana leaf-wrapped salmon, Korean short rib) and savory Asian pancakes (smoked bacon and kimchi).

And no Korean barbeque would be complete without a karaoke den where, thankfully, there’s a two-song minimum.

Belly Q, 1400 W Randolph St, Chicago, IL 60607; +1 312 563 1010; Monday-Friday: 11:30 a.m.-2:30 p.m.; Sunday-Wednesday: 5-10 p.m. (bar open until 11 p.m.); Thursday-Saturday: 5-11 p.m. (bar open until midnight); moderate

Mr. Beef's base take on the classic Chicago sandwich consists of beef dipped in broth and layered on a roll, then topped with sweet or hot peppers. Mr. Beef

If you’re serious about visiting Chicago, then you can’t leave until you have an Italian beef sandwich.

There’s much debate as to which is the best (Mr. Beef or Al’s), but Food Wars on the Travel Channel declared Mr. Beef the clear winner in 2010. And unlike Al’s, Mr. Beef isn’t a franchise. A favorite order is the signature dish, extra juicy, topped with spicy giardiniera. 

Mr. Beef, 666 N Orleans St, Chicago, IL 60610-3616; +1 312 337 8500; Monday-Thursday: 9 a.m.-5 p.m. and 10:30 p.m.-4 a.m.; Saturday: 10 a.m.-3 p.m. and 10:30 p.m.-5 a.m.; budget

Hot Doug’s

Many souls make the pilgrimage to Hot Doug’s in Avondale, even though the trip requires a car (or a train and a bus) to get there from downtown.

Chef and former punk rocker Doug Sohn churns out unique gourmet sausages every week, including favorites such as duck sausage with apple mustard and gyros sausage with tzatziki.

Chicago-style dogs are on the menu, too, and a side order of duck fat fries (available only on Fridays and Saturdays) is a must.

Hot Doug's Inc., 3324 North California, Chicago, IL 60618; +1 773 279 9550; Monday-Saturday: 10:30 a.m.-4 p.m.; budget

Pequod’s PizzaPepperoni and green pepper deep dish.

Chicago -- perhaps even more than New York -- is a serious pizza town. Whether you like it thin, Neapolitan or New Haven-style, there’s a slice for everyone.

But, of course, the local specialty is deep-dish pizza. Consuming a full slice is a challenge. Pounds of meat and cheese (all topped with a bucket of sauce) tend to sit in your belly for hours.

But a slice of sausage with perfectly caramelized crust at Pequod’s is worth the temporary pain.

Pequods Pizza, 2207 N. Clybourn, Chicago, IL 60614; +1 773 327 1512; Monday-Saturday: 11 a.m.-2 a.m.; Sunday: 11 a.m.-midnight; budget


AviaryWarning: the drinks at Aviary might make you feel under-dressed.

What Alinea is to food, Aviary is to drinks.

The average cocktail at this Grant Achatz lounge is $20, but it’s unlike any cocktail you’ve had. Every bartender here is a trained chef, so flavor rules above all else.

Like Alinea, the attention to presentation verges on the ridiculous. Ask for the Blueberry, and it comes out in a custom-designed clear cylinder that’s expertly packed with fruit, herbs and edible flowers.

There’s also a speakeasy downstairs, but you have to be invited to enter by someone on staff.

The Aviary, 953-955 W Fulton St, Chicago, IL; +1 312 226 0868; Tuesday-Friday: 6 p.m.-2 a.m.; Saturday: 6 p.m.-3 a.m.; expensive

Three drinks for the price of one. Scofflaw

Although Scofflaw is new on the scene, it’s already grabbed the top spot as the best bar in the city from Chicago magazine.

Head bartender and co-owner Danny Shapiro trained at The Whistler (another beloved cocktail bar in Logan Square) before opening this gin lounge.

The presentation is elegant but simple, many spirits are locally made and the interior is furnished with carefully picked salvage pieces.

Cocktails are only $8 -- yet another reason Scofflaw earns top honors.

Scofflaw, 3201 W Armitage Ave, Chicago, IL 60647; +1 773 252 9700; Sunday-Friday: 5 p.m.-2 a.m. and Saturday 5 p.m.-3 a.m.; moderate

It's great, outdoors. Big Star

Half taco hut, half whiskey joint, Big Star is the place for al fresco meet-ups in Chicago. When the weather is warm, the doors of this former garage in Wicker Park are raised and open tables disappear in a flash.

Paul Kahan, the chef behind Blackbird, Avec and Publican, crafted the food menu; the people behind The Violet Hour, a craft cocktail institution across the street, created the drinks.

Big Star, 1531 North Damen Avenue, Chicago, IL; +1 773 235 4039; Sunday-Friday: 11:30 a.m.-2 a.m.; Saturday: 11:30 a.m.-3 a.m.; moderate

Beer church. Hopleaf

In the past decade Chicago has opened four new breweries (Revolution, Half Acre, 5 Rabbit, Metropolitan), but the city’s love of beer was established long ago, thanks in part to Uptown gastropub Hopleaf and its diverse beer list.

The local hits are all on tap here, as are craft brews from across the country and a vast selection of Belgian ales.

In case that wasn’t enough, Hopleaf also stocks more than 250 bottled beers from North America and Europe.

Hopleaf Bar, 5148 N Clark St, Chicago, IL 60640-2828; +1 773 334 9851; Sunday-Friday: noon-2 a.m.; Saturday: noon-3 a.m.; moderate

Happy Village also hosts competitive table tennis, the world's happiest sport. Happy Village

Chicago is awash in neighborhood dive bars, many of them marked with a dim Schlitz sign and nothing else.  

Happy Village in Ukrainian Village stands out for its extras: checkered tablecloths, Ping-Pong, $2 PBRs and a homey back patio equipped with plastic chairs, strings of white lights and garden gnomes.

Happy Village, 1059 N Wolcott Ave between Augusta Blvd & Thomas St., Chicago, IL 60622-3760; +1 773 486 1512; Monday-Friday: 4 p.m.-2 a.m; Saturday: noon.-3 a.m.; Sunday: noon-2 a.m.; budget

Purportedly there are escape tunnels below the bar that date back to Prohibition. Perfect for first dates!Green Mill Cocktail Lounge


Like pizza and beer, jazz and Chicago are the perfect marriage, and for more than 100 years, the Green Mill has been the perfect place to cherish the union.

During Prohibition, Al Capone had a favorite booth, which still seats patrons. (Legend has it he liked it because he had a clear view of the front and back entrances.)

Today the Uptown club books some of the best jazz artists in the world, and for fans of word jazz, the Green Mill hosts a popular poetry slam every Sunday night.

Green Mill, 4802 N. Broadway Ave, Chicago, IL 60640; +1 773 878 5552; Monday-Friday: noon-4 a.m.; Saturday: noon-5 a.m.; Sunday: 11 a.m.-4 a.m.; moderate


The cafe's prices are considered reasonable. Ikram

Ikram Goldman won national attention as Michelle Obama’s stylist, but her eponymous boutique has dressed Chicago’s most fashionable women for more than a decade.

Goldman travels the world for the most cutting-edge designers. Alexander McQueen, Commes des Garçons, Prabal Gurung and Rodarte are just a few of the fashion houses she carries in her store, which quadrupled in size in 2011.

Ikram cafe, 15 East Huron Street, Chicago, IL 60611; + 1 312 587 1000; Monday-Saturday: 10 a.m.-6 p.m. (and by appointment); expensive

Penelope's stated style is "sophisticated yet fun." Penelope’s

For those unaccustomed to dropping $40,000 on a trip to Ikram, Penelope’s offers a wide selection of affordable clothing by the owners’ favorite “young and under-represented” designers.

Men and women can discover their inner Wicker Park hipster without any pressure or pretense from the store staff, who are always willing to gather a different size or strike up a friendly chat.

Penelope's; + 1 773 395 2351; Monday-Saturday: 11 a.m.-7 p.m.; Sunday: noon-6 p.m.; moderate

Purchase a lid off the hat rack, or have one custom made for the same price. Optimo Hats

Frank Sinatra, Charlie Chaplin, Lester Young. They all had their trademark hats, and at Optimo on the South Side, there are lids for every tony personality.

Storeowner and master milliner Graham Thompson crafts classic hats using the same techniques employed 50 years ago.

Thompson’s rising popularity (Johnny Depp is a fan, too) allowed him to open a second store in the historic Monadnock Building in the loop in 2012.
Optimo Hats, 10215 S. Western Ave.; +1 773 238 2999; Monday-Saturday: 10 a.m.-6 p.m.; expensive

Merz Apothecary

Since 1875, this family-run drugstore has been a haven for herbal remedies and European goods. The original location in Lincoln Square still fills prescriptions and still uses its original antique pharmacy jars.

Need a bar of soap for your stay? Merz has one of the largest collections of luxury bath products from around the world.

Merz Apothecary, 4716 North Lincoln Avenue, Chicago, IL; +1 773 989 0900; Monday-Saturday: 9 a.m.-6 p.m.; budget


The wing's "flying carpet" roof is a metal grid consisting of blades that block direct sun from the south, yet allow light from the north, conserving the works within. The Modern Wing at the Art Institute of Chicago

Like the Metropolitan Museum of Art in New York, you can spend an entire day at the Art Institute and cover only a fraction of the collection.

If time is limited, you can do a quick Ferris Bueller moment in the main building, before heading to the 264,000-square-foot Modern Wing to admire works by Matisse, Picasso and Miró under the natural light.

For lunch there’s Tony Mantuano’s elegant Terzo Piano on the third floor, where the spectacular view makes an advance reservation a necessity.

Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL 60603-6404; +1 312 443 3600; open daily: 10:30 a.m.-5 p.m. (Thursdays until 8 p.m.)

Chicago Architecture Foundation River CruiseThe tour covers more than 50 buildings along the Chicago River.

There are a number of boat tours on the Chicago River, but the Chicago Architecture Foundation River Cruise is the one that's most worth your time.

Enthusiastic CAF docents provide an engaging review of the city’s rich architectural history, and the perspective from the water is unlike (and far superior to) anything you’d experience at street level.

Chicago's First Lady Official Chicago Architecture Foundation River Cruise, Southeast corner of Michigan & Wacker, Chicago, IL 60611; +1 312 922 8687; tours start at 10 a.m. and typically run every half hour or hour depending on season; $37.85

Shhh ... the park still thinks the millennium began in 2004. Millennium Park

Although it opened four years behind schedule in 2004 and many taxpayers grumbled at its half-billion-dollar price tag, Millennium Park has become a critical darling.

Photos in front of the mirrored Cloud Gate sculpture, or “The Bean” as most people call it, have become a staple for tourists and locals, and on hot summer days, the Crown Fountain is a refuge for barefoot children in bathing suits.

The Jay Pritzer Pavillion, designed by Frank Gehry, hosts a slew of outdoor performances all summer long, and the competition for free lawn space is fierce.

Millennium Park, 201 E Randolph St Between Michigan Ave. & Columbus Ave., Chicago, IL 60602; +1 312 742 1168; open daily: 6 a.m.-11 p.m.


Chicago's as notorious for wit as it is for wind. You might catch tomorrow's biggest -- in many cases, literally -- comedians at one of Chi-Town's world-famous comedy labs.


Second City alums include John Candy, Bill Murray, Chris Farley, Tina Fey and Stephen Colbert. The Second City

Name almost any SNL breakout star -- John Belushi, Chris Farley, Tina Fey, Amy Poehler -- and chances are he or she served a stint in Chicago at Second City.

Chicago is the best place in the world to experience improv and sketch comedy, and the Second City revue (nightly except Mondays) and Monday night’s Improv All-Stars are safe bets that are always entertaining.

Those brave enough to test their improvisational skills are welcome to attend a drop-in class ($15; no experience required) at the training center on Sundays at 6 p.m.

Second City, 1616 N Wells St, Chicago, IL 60614; +1 312 337 3992; $16-$28

The theater is formerly known as Improv Olympic. iO

The iO is the true improv giant in town, and the theater’s signature show, "The Harold," is the definitive improv experience.

Founders Del Close and Charna Halpern invented the Harold technique, in which performers take a suggestion from the audience and create scenes and characters on the spot.

iO Chicago Theater, 1501 N. Kingsbury St, Chicago, IL 60642; +1 773 880 0199; performed nightly: $5-14 (free on Wednesdays)

The Neo-FuturistsFrom "Too Much Light Makes the Baby Go Blind."

The Neo-Futurists isn’t improv or sketch; it’s experimental theater mixed with moments of truth and hilarity.

Every weekend since 1988 the troupe has performed "Too Much Light Makes the Baby Go Blind," 30 short plays that are carried out in just 60 minutes. Each play is written by the ensemble and the lineup is constantly changing.

No two performances are the same.

The absurdity of the format -- with performers dashing around the stage at breakneck speed -- is worth a million laughs.

Neo-Futurists, 5153 N. Ashland Ave, Chicago, IL 60640; +1 773 878 4557; Friday-Saturday: 11:30 p.m., Sunday: 7 p.m.; prices vary