Difficulty: Moderately Easy
Step1
Get up and get breakfast. Chicago diners are fantastic whether you’re looking for basic pancakes and sausage or an exotic breakfast skillet. Try the storied Lou Mitchell’s when you’re in the central business district or Orange Café if you feel like having a pancake flight. If you’re off the famous Michigan Avenue, grab some coffee and a big breakfast at Tempo Cafe. Melrose is in the diverse Lakeview neighborhood.
Step2
Do lunch. If you want it fast, visit The Wiener’s Circle on North Clark Street. It's a no-frills, 24-hour hot dog and burger hole. The fresh, hot fries are even better if you get the cheddar dumped on them. Nearby is Café Luigi, serving delicious New-York-style pizza. At the north end of Michigan Avenue is Oak Tree, in the middle of some high-end shopping. It offers a great menu, tasty desserts and wonderful views from its sixth-story windows. 312 Chicago offers fine dining across from City Hall in the financial district.
Step3
Enjoy your dinner. Closer to downtown and the Near West Side, try Naha for Mediterranean-Californian inspiration, Japonais for modern Japanese, DeLaCosta for Latin flavors in a lounge setting or highly-respected One Sixtyblue for modern French. And for the price, you can’t beat the taste at Twist, a tapas place in Wrigleyville. Just off Lake Shore Drive in Lincoln Park is North Pond Café, a fine-dining gem serving seasonal French-American. Go to one of the 14 Giordano’s restaurants in Chicago if you want the city’s best deep-dish pizza.
Step4
Get grub when it’s late. El Presidente Mexican restaurant and the diner Michael’s North are both 24-hour joints in the Lincoln Park neighborhood. The infamous Billy Goat Tavern welcomes you day or night underneath Michigan Avenue--a local would easily scarf down 2 doubles with cheese.