There are more than 300 restaurants participating in Restaurant Week (January 27 to February 9), so how did I whittle my list down to five? I went menu bargain hunting online—comparing normal prices to restaurant-week prices at the best restaurants in town.

But it's only a good deal if the restaurant's worth visiting in the first place, so I centered on spots I love any day of the year. 

Here are my picks, complete with menu choices, course by course.

Balena: 4-course dinner, $44

Balena feels hipstery—the kind of place that could get by on its looks. Maybe it could, but this is one serious restaurant that never takes its success for granted. I particularly love that the menu goes against the grain and does not constantly change. That means when I grow attached to a dish—like the plate of spicy lamb meatballs—I can have it again and again and again.

Penny's order:
Course 1: Spicy lamb meatballs
Course 2: Gnocchi
Course 3: Blue prawns with white beans
Course 4: Dark chocolate panna

Cafe Spiaggia: 3-course lunch, $22

Ever swanky and always delicious, 32-year-old Cafe Spiaggia is a gem for a leisurely adult lunch. In my book, that means a table for two by a window overlooking North Michigan Avenue, a patch of park, and a glimpse of Lake Michigan. I’ll settle in with a glass of prosecco every time.

Penny's order:
COURSE 1: Tomato soup with mascarpone, fennel, and brown butter
COURSE 2: Wood-grilled eggplant crostino
COURSE 3: Orange zest tart

Capital Grille: 4-course dinner, $33

Dry-aged beef, plush booths, and professional waiters are the hallmarks of fine steakhouses all over town, so why Capital Grille? I really dig the calm nature of the handsome dining room. As for Restaurant Week, CG is the bomb. I did the numbers: At $33 for four courses, it’s practically like scoring a steak for free.

Penny's order:
COURSE 1: Wedge Caesar
COURSE 2: 14-oz bone-in dry-aged NY strip
COURSE 3: Heirloom tomatoes and French green beans
COURSE 4: Flourless chocolate espresso cake

Frontera Grill: 2-course lunch, $22

Frontera Grill is the place that turned my head around about regional Mexican dishes. The guacamole, ceviches, and margaritas at Rick Bayless’s flagship regional Mexican restaurant never fail to rock my finicky taste buds.

Penny's order:
COURSE 1: Hawaiian albacore ceviche
COURSE 2: Tacos arabes with grilled spiced pork and caramelized onions

Sepia: 3-course dinner, $33

Being at this just-off-Randolph-Row spot always makes me feel a little smug. Plenty of people eat here—all the time—but somehow Sepia feels like Chicago’s best-kept secret. The menu reads like a global homage to fine dining, because it is!

Penny's order:
COURSE 1: Rabbit ravioli
COURSE 2: Smoked bluefish
COURSE 3: Chocolate hazelnut tart, but I wouldn’t blame anyone for choosing the ginger lime parfait