Italian beef, barbecue, Maxwell Street polish sausages, craft beer—Chicago is home to countless iconic (and cheap) eats. And there are just as many food-centric neighborhoods, from the bakeries of Little Italy, to the curry-scented dining rooms of West Rogers Park. Our mouths watering, we wondered: How many classic Chicago restaurant experiences could we possibly pack into a single weekend?

Using Groupon’s new Groupon+ deals as our guide, we dreamed up this weekend dining challenge, filled with 14 Chicago restaurants and more than $67 in cash back—enough to purchase plenty of elastic-waist pants.

Day 1: Friday

Happy Hour at Stocks & Blondes

40 N. Wells St. | The Loop

Chicago is a city of dive bars, even in the franchise-heavy Loop. And this low-key spot under the Washington-Wells ‘L’ stop is a perfect spot to kick off the weekend. It also keeps the flavor local with drafts from area breweries such as Revolution and Half Acre.

Sample menu: two draft beers ($6 and $8, respectively) and an order of Forbes nachos covered in chili ($9.50).

Total bill (without tax): $23.50
Groupon+ deal: 10%
Total cash back: $2.35

Dinner at Robinson’s #1 Ribs - Union Station

225 South Canal St. | The Loop

Based in suburban Oak Park, Robinson’s is known for its award-winning ribs and secret sauce. Fortunately, the Union Station location also serves these specialties and is just brisk walk from Stocks & Blondes.

Sample menu: ribs and shrimp combo served with a roll, coleslaw, and a choice of beans or steak fries ($19.95), plus a large, 20-ounce fountain drink ($1.59).

Total bill (without tax): $21.54
Groupon+ deal: 30%
Total cash back: $6.46

Dessert from Ge Pa De Caffe

60 E. Adams St. | The Loop

Keep an eye on the clock, as this downtown Italian café closes at 5 p.m. But planning ahead is worth it. After all, Ge Pa De Caffe is home to the most authentic cannoli this side of Taylor Street. Eat one on the spot and save the second for your trip home.

Sample menu: two cannolis ($7) and a Nutella cappuccino ($4.05).

Total bill (without tax): $11.05
Groupon+ deal: 20%
Total cash back: $2.21

Day 2: Saturday

Breakfast: Cafe on the Grove

4317 S. Cottage Grove Ave. | Kenwood

One of the best ways to start a Chicago weekend is with a breakfast of made-from-scratch soul food, and this South Side spot doesn’t disappoint.

Sample menu: jerk shrimp served atop creamy, cheddar cheese grits ($13) with a side of homemade biscuits ($1.55) and a cup of house-blend coffee ($2.50); OK, and a slice of red velvet cake to go ($4.50).

Total bill (without tax): $21.55
Groupon+ deal: 20%
Total cash back: $4.31

Lunch at Harold’s Chicken 88

124 East 35th St. | Bronzeville

No itinerary of the best places to eat in Chicago would be complete without a stop at this beloved comfort-food spot, widely considered the best fried chicken in town.

Sample menu: half mixed-chicken dinner ($7.45), small order of fried gizzards ($5.50), slaw ($2.75), and a large hot sauce ($2).

Total bill (without tax): $17.70
Groupon+ deal: 25%
Total cash back: $4.43

Mid-Afternoon Snack at Jim’s Original Hot Dog

2050 S. Union Ave. | Little Italy - University Village

Chicago is known for its fully loaded hot dogs, but there’s another famous sausage in town: the Maxwell Street polish hot dog. Founder Jimmy Stefanovic invented the renowned dog almost 70 years ago, and the rest is caramelized-onion-topped history.

Sample menu: polish sausage sandwich ($4.50) with a free bag of fries, plus a bottle of pop ($2.15).

Total bill (without tax): $6.65
Groupon+ deal: 10%
Total cash back: $0.67

Dinner at Chez Moi

2100 N Halsted St. | Lincoln Park

Despite being better known for cheap eats, Chicago is home to a fair share of fine French restaurants. This one—a collaboration between chef Dominique Tougne and Blackhawks player Cristobal Huet—is perfect for a romantic evening, so bring a potential paramour.

Sample menu: two french onion soups ($16), duck-confit cassoulet ($27), beef bourguignon ($27), crème brûlée to share ($8.75), and a bottle of Varichon et Clerc, brut rosé ($40).

Total bill (without tax): $118.75
Groupon+ deal: 20%
Total cash back: $23.75

Drinks at Cesar’s

2924 N Broadway | Lakeview

Chicagoans know this spot for its giant neon sign reading “Home of the Killer Margarita”. And that’s why you’re here.

Sample menu: two Killer margaritas, any flavor ($12 each).

Total bill (without tax): $24
Groupon+ deal: 20%
Total cash back: $4.80

Late Night Music and Drinks at B.L.U.E.S. on Halsted  

2519 N Halsted St. | Lakeview

If dinner and drinks go well, impress your date with a trip to this intimate blues club, where performers play tunes until 2 a.m.

Sample bill: two covers ($10 each) and two well cocktails ($5 each).

Total bill (without tax): $30
Groupon+ deal: 30%
Total cash back: $9

Day 3: Sunday

Breakfast at Bru

1562 Milwaukee Ave. | Wicker Park

A late night means a late morning, so skip a fancy sit-down breakfast and perk up with a cup of coffee made with beans from local roaster Bow Truss.

Sample menu: 16-ounce latte ($4) and croissant sandwich with egg, cheddar, and avocado ($7.25).

Total bill (without tax): $11.25
Groupon+ deal: 10%
Total cash back: $1.13

Lunch at Al’s No. 1 Italian Beef

3420 N. Clark St. | Wrigleyville

No Chicago foodie quest would be complete without at least one italian beef sandwich. And there’s no better place to visit than this beloved institution, which has been dishing out the juicy delicacies since 1938.

Sample menu: Regular beef ($6.59) with hot giardiniera ($0.55) and cheddar ($0.55), plus a large fry ($3.50) and can of pop ($1.39).

Total bill (without tax): $12.58
Groupon+ deal: 25%
Total cash back: $3.15

Drinks at The Globe Pub

1934 W. Irving Park Rd. | North Center

Whether you’re into American or European football, this British pub is the perfect place to catch the game thanks to its more than 30 televisions and 400 beers.

Sample menu: Goose Island Green Line draft ($5) and a bottle of Finch’s Fascist Pig Ale ($7).

Total bill (without tax): $12
Groupon+ deal: 20%
Total cash back: $2.40

Dinner at Daata Darbar

2306 W. Devon Ave | West Rogers Park

There’s certainly no shortage of excellent Indian restaurants along Devon Avenue, but this one stands out with its authentic menu.

Sample menu: veggie samosas ($2.49), mutton biryani ($7.99), paratha ($1.25), and a sweet lassi ($3), plus a chicken paratha roll ($3.99) for lunch tomorrow.

Total bill (without tax): $18.72
Groupon+ deal: 10%
Total cash back: $1.87

Dessert at Taza Bakery

3100 W. Devon Ave. | West Rogers Park

While you’re in the neighborhood, drop into this Middle Eastern bakery for a sweet treat. We recommend its kneffee ($5.99)—a cheese-based pastry soaked in sugar syrup.

Total bill (without tax): $5.99
Groupon+ deal: 10%
Total cash back: $0.60

Menu items and prices are subject to change.