Editor’s Note: CNN Insider Guides are thoroughly checked for accuracy. Given the fluid nature of the travel industry, however, some listings may fall out of date before guides can be updated. The best practice is to confirm current information on official websites before making plans to visit any business or attraction.
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 giant 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.
Hotels
Luxury
Waldorf Astoria
Travel + Leisure frequently ranks the Waldorf Astoria (formerly the Elysian) as one of the top large-city hotels 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.
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.
Mid-range
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.
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.
Budget
Inn at Longman & Eagle
In recent 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.
Dining
Alinea
Although Alinea has slipped a little in the ranks of the World’s Best Restaurants list, chef Grant Achatz still draws crowds with his 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.
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 $250 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.
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.
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.
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.
Pequod’s Pizza
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.
Nightlife
Aviary
Warning: 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.
Scofflaw
Since opening in 2012, Scofflaw has earned a spot as one of the best bars in the city.
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.
Many cocktails are only $8 – yet another reason Scofflaw earns top honors.
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.
Hopleaf
In the past decade Chicago has opened a bevy of new breweries, 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.
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.
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.
Shopping
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.
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; 1913 W. Division St., Chicago, Illinois; +1 773 395 2351
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
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.
Attractions
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.
Chicago Architecture Foundation River Cruise
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.
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.
Comedy
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.
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.
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.
The Neo-Futurists
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.
