5 Tips for Dining in Chicago

How to navigate the Chicago restaurant scene

As one of the world’s most brilliant food cities, Chicago’s dining options are abundant, mind-blowing—and perhaps a little daunting. Get the most out of eating out with these five tips.  

No Jacket Required

Few restaurants in Chicago enforce a rigid dress code, but for most of us, the more expensive the meal, the fancier the get-up. No restaurant in Chicago requires a tie, but you’ll just feel better if you wear a jacket to any place with Michelin stars. If you’re not sure about the vibe of the restaurant, you can’t go wrong with business casual. Count on most places with white tablecloths to draw the line at flip-flops and tank tops, but aside from that, you’re pretty much able to come as you are.

Tasting Menus? Go for It

Tasting menus are a fine way to sample a chef’s favorite dishes. Some esteemed restaurants—like three-starred Alinea (1723 N. Halsted, 312.867.0110) and Grace (652 W. Randolph, 312.234.9494)—serve only tasting menus. At places like these, the tasting menu is more than just a collection of dishes; it’s a sequence, a composition of different tastes that add up to an unforgettable dining experience. 

Look Beyond Big Names & Go Ethnic

In the city of neighborhoods, it would be a big mistake to limit your dining adventures to downtown restaurants. Smaller, ethnic places in the neighborhoods deliver memorable meals under $20. La Chaparrita (2500 S. Whipple St., 773.247.1402) has received national recognition as one of the country’s best taco places. Rainbow Thai Cuisine (4825 N. Western Ave., 773.754.7660) lays out outstanding Southeast Asian chow that’s in no way dumbed down for general consumption. Ghareeb Nawaz (2032 W. Devon Ave., 773.761.5300) is Pakistani, and the biryani will blow your mind, a complex blend of rice and multiple spices, a powerful mouthful. For a small investment, ethnic restaurants introduce diners to new flavor combinations.

Wine Pairings: Split the Pour, Enjoy More

Wine pairings enable the sommelier—who is intimately familiar with each dish’s component ingredients—to choose wine that goes best with each course. Problem is, with so many glasses of wonderful wine, you’re likely to, um, “lose focus” long before dessert arrives. Moreover, a premium wine pairing can cost almost as much as the meal. At Alinea, we paid around $150 for the wine pairing and around $200 for the tasting menu. When you’re dropping serious coin on dinner, you want the food to be equally important as the drink. Splitting a wine pour with a friend goes easier on the budget without limiting the experience.  

Yes, Splurge on the Steak

Chicago has some of the most innovative chefs anywhere and it’s been more than 40 years since the Union Stockyards closed. Yet, this is still a meat and potatoes city, one of the best places on earth for killer steak. It makes sense: We have a meat-loving heritage, local ranchers who know what they’re doing, and a slew of superb steakhouses, all competing to serve the finest red meat in town. If you have steak on the brain, check out David Burke’s Primehouse (616 N. Rush, 312.660.6000), Smith & Wollensky (318 N. State, 312.670.9900) or Chicago Cut Steakhouse (300 N. LaSalle, 312.329.1800). Maybe you don’t eat beef everyday (honestly, you probably shouldn’t) but when here, you’re missing out if you don’t order what will become your benchmark for beef.