Summer of Go: Chicago

Summer of Go: Chicago


In true Tommy Bahama fashion, we're celebrating the season of sun in style from coast to coast. Over the years, we've made friends in all the right places: Boston, Baltimore, Tampa, Chicago, New Orleans, Seattle, San Francisco and Kona, to name a few. During this “Summer of Go,” we'll share our favorite things to see, do and experience in each of those locales.


Chicago, you’re our kind of town: Glimmering metropolitan sophistication standing arm in arm with that famous Midwestern warmth. We dig your food scene, artistic chops, astounding architecture and of course, those swingin’ beaches. You’re holding up a lot with those big shoulders.

In 1883, when the city was the ripe ol’ age of 46, Mark Twain said, “It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them.” And it’s never been a city that enjoys standing still. America’s busiest aviation center and hub to 50% of its rail freight is also home to the first US skyscraper, the origin of Route 66, refrigerated rail cars, mail-order retail and the car radio. It has “Go” written all over it. Here are some of our picks for digging into the Windy City.


Cruise for Views
See the city from a different perspective on the Chicago Architecture Foundation’s boat tour. The First Lady fleet floats you down all three branches of the Chicago River, showing off the city’s many architectural marvels. Between the docents’ encyclopedic knowledge of the buildings and the full-service bar onboard, it’s truly a pleasure cruise.

Millennium Park It
Conceived as “a new kind of town square,” Millennium Park is a haven of contemporary greenspace and sculpture. Take a pic of your reflection in “the Bean” (the giant, mesmerizing Cloud Gate), meander the Lurie Garden and get splashed in the water “spat” from the digital faces of Crown Fountain. Pack a picnic for the Great Lawn – you may luck into a free performance in the Pritzker Pavilion. Part of Grant Park, it’s an ever-evolving jewel in the city’s crown.

Enjoy the Drama
Chicago’s a theatre town, and you’ll find great performances every night of the week. Storefront spots offer both avant-garde and classic works, while powerhouses like Steppenwolf, the Goodman and Chicago Shakespeare Theater turn out critical darlings that often make it to Broadway. And the city’s reputation for improv is well-deserved; check out The Second City, iO and The Neo-Futurists for a fulfilling fix.

Get Institution-alized
Past two majestic lions lies what’s often called the best museum in the country: The Art Institute of Chicago. Its massive collection spans 5,000 years and features more iconic works than you can shake a paintbrush at. Get serious with American Gothic, look for the other images painted beneath the Old Guitarist and make a date with pointillism in front of Seurat. Leave time to bask in the glow of the Chagall Windows and to cruise the Modern Wing. Don’t miss the often-overlooked Stock Exchange Trading Room and the Thorne Rooms.

Stroll the Magnificent Mile
This stretch between the Loop and the Gold Coast is packed with history and endless shopping. It technically starts at the river, but begin at Michigan Ave and East Wacker Place – here you’ll find the audacious Deco gem supposedly inspired by a champagne bottle, the Carbide & Carbon Building. Amble north to the Wrigley Building and Tribune Tower, up past the fire-surviving Water Tower, and all the way to the Drake Hotel on ritzy East Lake Shore Drive. Celebrate your athleticism with a drink on the 96th floor of the Hancock (oddly, the best views of the city are from the bathrooms).

Root, Root, Root for the Cubbies
Chicago is a sports lover’s paradise, and no trip here is complete without a pilgrimage to Wrigley Field. Home to the Cubs since 1916, it marks its 100th season this year. The Friendly Confines has witnessed scores of milestones (including The Babe’s infamous “called shot” in 1932), and still boasts ivy-covered outfield walls and a hand-turned scoreboard. Enjoy the view from upper deck over the main entrance and go bar-hopping in Wrigleyville when the game’s over.

Play Beach Blanket Bingo
With 26 miles of shoreline and 33 beaches, opportunities for serious relaxing abound here. Every spot has its own vibe; grab your towel and find one that speaks to you. From Foster Avenue Beach on the far North Side to 63rd Street Beach in historic Jackson Park, there’s abundant sunbathing opportunity. For sports and socializing, try North Avenue, and for swimming, chess and a nosh, head to Oak Street. Want to hit more than one? Use Chicago’s new Divvy bike sharing system for cheap and easy transportation.


953 W Fulton Market /
Why we love it: Grant Achatz is Chicago’s only three-star Michelin chef, and his latest tasting haven offers a totally unique experience: a complete shift in theme and menu every few months. From “Paris: 1906” to “Childhood,” the chef’s imagination is your culinary playground. Use their innovative ticketing system to book a table and pre-pay (well in advance).

Hot Doug’s
324 N California Ave / 773.279.9550 /
Why we love it: Trying a Chicago Dog is a must, so HURRY to this beloved institution before it closes its doors on 10/4/14. Featuring both the classic and more “foodie” offerings, the duck fat fries and Game of the Week dog are can’t-miss picks.

David Burke’s Primehouse
616 N Rush St / 312.660.6000 /
Why we love it: The Chicago steakhouse gets a swinging spin here, where the stars of the show are the dry-aged cuts of beef. Don’t skip the tableside-prepared Caesar (spike it with chili oil), and once you’ve polished off dinner, tour the Himalayan salt-tiled aging room to see where the magic happens.

851 N Ashland Ave / 312.624.8509 /
Why we love it: A welcoming atmosphere makes this tiny enclave of inventive comfort food a delight to be savored. Built from an “all-things-reclaimed” spirit and part of Chicago’s famous BYOB culture, it’s regarded as one of the best bangs for your buck — and your palate — anywhere.

Girl & The Goat
809 W Randolph St / 312.492.6262 /
Why we love it: Chef Stephanie Izard won Top Chef … and then she won a James Beard Award. Making the seemingly simple absolutely delectable is the name of the game here, and the warm atmosphere will win you over. You won’t regret ordering “pig face” anything, and yes, there’s always goat on the menu.

445 N Clark St / 312.661.1434 /
Why we love it: Turning out beautiful plates since the 80s and still going strong, this sleek and daring establishment has been called the most elegant Mexican restaurant in the country. Order from categories like “Vibrant,” “Soulful” and “Luxurious,” and truly match your food to your mood.

Nico Osteria
1015 N Rush St / 312.994.7100 /
Why we love it: Rustic and refined collide gracefully at this paean to Italian-style seafood. Indulge in irresistibly fresh whole fish and house-made pasta while unpretentious servers help you navigate the Greco-Italian wine list. And then come back the next morning for the dreamy kouign amann pastry.

The Publican
837 W Fulton Market / 312.733.9555 /
Why we love it: A self-declared “homage to beer, pork and oysters,” this expansive eatery was created to showcase the farmers’ and fishermen’s bounty. After you’ve feasted, pick up some treats to trick out your own charcuterie platter at their sister butcher shop/market/deli, Publican Quality Meats.


Three Dots and a Dash
435 N Clark St / 312.610.4220 /
Why we love it: Chicago’s new favorite bar is a serious throwback all the way to the Tiki heyday. But within these skulls and coconut shells, there’s some expert mixology going on. Tippling with a group? Make it memorable and drink Dom and aged rum from your very own smoking treasure chest.

The Aviary
955 W Fulton Market / 312.226.0868 /
Why we love it: Grant Achatz’s cocktail bar is elevating booze to gastronomic new heights. Whimsical, over-the-top and unabashedly inventive, it’s an imbibing experience unlike any other. Prepare to be dazzled.

The Green Mill
4802 N Broadway Ave / 773.878.5552 /
Why we love it: With its original murals and Al Capone’s favorite half-moon booth ripe for the snagging – just west of the bar and facing the door – drinking here feels like going back in time. In existence for 107 years, its lore is legendary. (Escape tunnels, anyone?)

Intelligentsia Coffee
53 W Jackson Blvd / 312.253.0594 /
Why we love it: It’s a coffee joint, but it may be the best joe in the country. With several outposts in the city, this one features the vintage styling of an Italian espresso bar and lives in the historic Monadnock Building.

The Violet Hour
1520 N Damen Ave / 773.252.1500 /
Why we love it: With their precision cocktail execution, the balletic bartenders at this swanky Wicker Park speakeasy have earned it a rep as one of the best bars in the world. There’s no sign; you’ll know you’re there when you spot the yellow light bulb over the door.

Pops for Champagne
601 N State St / 312.266.7677 /
Why we love it: People have been toasting triumphs here for over three decades. With a menu that includes around 200 selections of sparklers and small plates that cater to them, these tiny bubbles will have you feeling absolutely fine.

5148 N Clark St / 773.334.9851 /
Why we love it: This warm and busy Andersonville gastropub is widely considered the city’s best beer bar. Brews and contemporary eats lean toward Belgium, but over 65 taps and 350 bottles leave plenty more of the world of suds to explore.