Travel Tips

Three Days, Nine Meals (or More): Chicago, Illinois

Locations in this article:  Chicago, IL

Blackberry at AlineaChicago’s culinary concoctions are a major part of the city’s charm and are not to be missed on a trip to the famous Windy City.

Enjoy both high-class dining experiences and traditional Midwestern, down-home cooking options by visiting some of the most delicious restaurants Chi-town has to offer.

You may gain a few pounds, but hey, that should come in useful during the cold Chicago winters…



Start with a true Chicago feast! The front façade of Gino’s East of Chicago is adorned with spotlights made out of neon tubes lighting up the large letters of this Chicago hotspot. For those who are devoted to Chicago-style pizza, this is the Mecca.

Gino’s East These deep-dish pies are so thick you have to eat them with a fork! Gino’s is known for its signature polenta crust, which is crispy and has a distinct bite. The cheese is an ultra-creamy mozzarella with a spiced tomato sauce. If you want a real Chi-town experience, get the signature Chicago pie—with extra cheese and sausage. Pizza-haters, have no fear … Gino’s also serves large-portion sandwiches and pasta dishes. 633 N. Wells Street;


After a casual lunch, go high-class for dinner. One top recommendation is Tru, a new-wave French restaurant that mixes classic French cuisine with some modern techniques. The dinning room is open with white walls covered in contemporary art pieces (tip: look through them to find an original Warhol!).

Dishes at Tru Restaurant The food itself is another work of art, starting with a caviar appetizer served cascading down a small glass staircase. The must-have entrée is the venison loin with creamed corn, a grit cake and served in its own venison jus. Know how much you want to spend before you go, because the food at Tru is prix fixe: $80 for a three-course menu, $100 for a seven-course, and $135 for the chef’s collection. 676 N Saint Clair St # 1; 312-202-0001,

If French isn’t your thing, grab some sushi at sushi wabi in the Market District. The dark and industrial ambiance is practically the opposite of Tru, but is hip to the core. From 7 p.m. to 11 p.m. a DJ spins thumping progressive jazz. Sushi wabi definitely has a club-like vibe, but appeals to wide audiences with fun and funky sushi rolls. They offer 25 colorful and elaborate creations with familiar rolls like the dragon or the spider and unique items like the “large tarantula,” which is stuffed with two kinds of crab, avocado, veggies, and a special sauce. Wabi also is a great place to branch out from sushi. The seared sea scallops paired with a tart apple plum puree is a memorable plate. 842 W. Randolph; 312-563-1224,



Walker Bros Apple PancakeStart out your day with a Chicago standard, Walker Bros. Original Pancake House. The ’50s-style décor features Tiffany stained-glass lamps and worn, wooden high-backed booths. As you may expect, this spot is known for its endless variety of pancakes. If you must choose just one, go for the Apple Dutch Baby—a lighter-than-air pancake that rises in the oven and is smothered with hot, juicy cinnamon apples. Besides carb-laden breakfasts, there is also a selection of fluffy oven-baked quiches and omelets. 1615 Waukegan Road;


Hot Doug’s LogoAfter your large breakfast, a smaller lunch may be in order, but you can still do it in true Chicago tradition … like a hot dog! You’ll know you’re at Hot Doug – The Sausage Superstore and Encased Meat Emporium – by the wiener paraphernalia covering the walls.

Go for the Chicago-style dog, which includes a poppy seed bun with mustard, bright green relish, onion, tomato wedges, a pickle spear, sport peppers, and a dash of celery salt, but never ketchup. If you can handle it, try a bratwurst or a “celebrity dog of the week” made out of such meats as venison, elk or wild boar. Whatever you choose, get an order of French fries cooked in duck fat—yes, duck fat—and say goodbye to your waistline. 3324 North California; 773-279-9550,


Chicago has a large Greek population and Greek Town neighborhood is not to be missed. Santorini is less touristy and more elegant than its neighboring restaurants. The whitewashed walls are decorated with baskets and copper pans and a large fireplace invites warmth on a cold winter night. The table-side filleting of your meat is a homey touch. Try to go on a Thursday or Sunday when the special is barbequed lamb so juicy it falls of the bone, perfectly complemented by lemon potatoes. 138 S Halsted Street; 312-829-8820,

Or, check out Joe’s Seafood. It is designed like a 1940s “old boy’s club,” something that is still popular in Midwestern cities today. The fare is surf and turf and marked by the simple quality of the food’s preparation. The signature dish is a meaty stone crab claws, but any fish or steak dish will please. Get at least one order of Jennie’s Potatoes, a pile of crispy fries topped with extra cheese. 60 East Grand; 312-379-5637,

Late-Night Fare

Crostini at Avec RestaurantNo matter what the season, Chicago has a thriving nightlife, which means that you’re sure to work up an appetite. No foodie trip to this city is complete without a visit to Avec. The décor is sleek, with bare cedar walls and a stainless steel bar.

Guests sit at communal tables, so get ready to make new friends. The cuisine is Mediterranean, and most items are cooked in a wood-burning oven and served in cast-iron dishes. Try the crispy focaccia with taleggio cheese and truffle oil, and pair it with a glass (or two) from the expansive wine menu. 615 W. Randolph; 312-377-2002,



Start your day with a morning meal at the Bongo Room. This is going to be sugary breakfast, but well-worth the unusual flavors. Some pancake options include brown sugar-pecan with banana or ginger-walnut with warm maple cream. Try to balance out the sweetness with the tasty hash browns, served crunchy with lots of dill and no greasy aftertaste. 1152 S Wabash Avenue; 312-291-0100


Billy Goat Tavern“Cheezborger! Cheezborger! Cheezborger! No fries, cheeps! No Pepsi, Coke!” That mantra, made famous by Saturday Night Live, came from the Chicago burger joint Billy Goat Tavern.

Billy’s is located under the El in a dingy, yet iconic location. The restaurant is also the origin of the famous “Cubs Curse,” in which the original owner of the Tavern brought his goat to Wrigley Field—when he was kicked out, he cursed the Cubs to never win another World Series. No matter what you order, the cook will berate you into getting the “double cheez,” which actually is an excellent choice. 430 N. Michigan Avenue; 312-222-1525


Alinea TomatoKeeping with the Americana theme, try Alinea for an evening meal. To get to the dining room you have to travel down a narrow passageway and go through motion-detecting metal doors that let you know that your dining experience will be something different. The dishes are New American and served with creative silverware and even some with instructions. The chef is progressive in his flavors and presentations—don’t be surprised if your bison steak with blueberries is served with a cinnamon stick on a hot rock, or your Maine lobster is topped with an eggplant mousse. 1723 North Halsted; 312-867-0110;

Rick BaylessGo south of the border with a dinner at Topolobampo. This is gourmet Mexican cuisine like you have never tasted, with a menu created by celebrated chef Rick Bayless. Every meal is made with the freshest ingredients and served by very knowledgeable waiters. The décor is sparse but colorful. Make sure to pair your meal with any of the options from the fantastic wine list or an interesting cocktail from the bar. 445 North Clark Street; 312-661-1434,


End your gastronomical trip to Chicago on a sweet note with a trip to Margie’s Candies. The restaurant has an “olde-time parlor” feel with the staff donning bow ties and vests. If you dare, go for the ice cream sundae—it’s served in a seashell bowl and is as big as your head. The caramel and hot fudge are homemade and served piping hot. Don’t forget to purchase some hand-dipped chocolates to enjoy when you’re back at home! 1960 N. Western Avenue; 773-384-1035

Your trip to Chicago will leave you so full that you won’t have to worry about the gusty winds blowing you over!

By Courtney Crowder for

Looking for another quickie culinary tour? Check out Three Days, Nine Meals (or More): New York City.

Still hungry? Don’t miss our complete Culinary Travels section.

Don’t miss our Off the Brochure Travel Guide to Chicago, Illinois.