$70 a Day in Chicago: Our Cheap Eats Food Challenge (In the Frozen Windy City)
Chicago in the winter is… a choice. The wind is personal, your fingers stop working mid-sentence, and somehow there’s always a guy jogging in shorts like he’s built differently.
So naturally, Chris and I decided to film a Cheap Eats Chicago challenge: $70 total for breakfast, lunch, dinner, and a snack (tax + tip included)—while chasing the foods people actually search for when they visit Chicago: cinnamon rolls, Italian beef, deep dish, and the classic Chicago snacks.
If you’re planning a trip and want a one-day Chicago food itinerary that’s fun, tourist-friendly, and still feels like you’re eating the real Chicago, here’s exactly what we did—with prices, what to order, and where to go.
The $70 a Day Rules
Budget: $70 per person (including tax + tip)
Meals: breakfast + lunch + snack + dinner
Goal: hit Chicago icons and keep it affordable
Cheap Eats Chicago a Random Recess Food Challenge
Stop 1: Ann Sather — Cinnamon Rolls That Live Up to the Hype
What to order: Cinnamon rolls (the famous ones)
Why it’s worth it: Warm, gooey, glazed, and shockingly budget-friendly
We started early at Ann Sather’s Belmont location—an old-school Chicago staple that’s basically a cinnamon-roll pilgrimage spot.
Cost: $5.70 total (for two cinnamon rolls, tax + tip included)
Running budget: $64.30 left
📍 Ann Sather (Lakeview / Belmont) — 909 W Belmont Ave, Chicago, IL 60657
Ann Sather’s Chicago, IL
Quick Chicago Must-Do: “The Bean” at Millennium Park
You can’t not do it. Quick photo stop, quick wish, quick reminder that Chicago wind is undefeated.
📍 Cloud Gate (“The Bean”) — Millennium Park, 201 E Randolph St, Chicago, IL 60602
The Bean at Chicago’s Millennium Park
Stop 2: Al’s #1 Italian Beef — The Lunch I’ve Been Dreaming About
What to order: Italian beef (dry, wet, or dipped—your choice)
Our move: “Wet” + au jus on the side so we could control the chaos
This is one of the top “must-eat” Chicago foods for a reason: the beef is juicy, the flavor is rich, and it’s the kind of lunch that makes you immediately start planning how to squeeze in another one before your flight home.
Cost: $11.41 (tax + tip included)
Running budget: $52.89 left
📍 Al’s #1 Italian Beef (River North) — 548 N Wells St, Chicago, IL 60654
Al’s #1 Italian Beef
Stop 3: La Bomba — The Chicago Jibarito (Neighborhood Food Win)
What to order: Steak jibarito + rice
Why it’s a Chicago flex: It’s not deep dish… It’s Chicago’s Puerto Rican icon
If your idea of “Chicago food” stops at pizza and beef, this is your sign to explore neighborhoods. The jibarito is a sandwich-style masterpiece that swaps bread for fried plantains—and it works.
Cost: $13.95 (tax + tip included)
Running budget: $50.35 left
📍 La Bomba — 3221 W Armitage Ave, Chicago, IL 60647
La Bomba Chicago, IL
Walk It Off: Field Museum
We spent a few hours at the Field Museum to earn our snack(s). If you’re traveling with family—or you just love a solid museum day—this is an easy win.
📍 Field Museum — 1400 S DuSable Lake Shore Dr, Chicago, IL 60605
The Field Museum Chicago
Stop 4: Jim’s Original — Maxwell Street Polish Sausage Snack
What to order: Maxwell Street Polish
Why it hits: Snap + sweet onions + mustard + instant warmth in winter
This was one of those “simple but perfect” Chicago moments—no frills, just iconic street food done right.
Cost: $8.50 (tax + tip included)
Running budget: $41.85 left
📍 Jim’s Original — 1250 S Union Ave, Chicago, IL 60607
Jim’s Original — Maxwell Street Polish Sausage Snack
Stop 5: Garrett Popcorn — The Chicago Mix Classic
What to order: Garrett Mix / “Chicago Mix” (caramel + cheese)
There are snacks… and then there’s Garrett’s. It’s sweet, salty, addictive, and feels like a Chicago “souvenir” you can eat on the walk back to the hotel.
Cost: $8.89
Running budget: $44.00 left (after this snack)
📍 Garrett Popcorn Shops (Magnificent Mile) — 625 N Michigan Ave, Chicago, IL 60611
(Alt location near Millennium Park: 173 N Michigan Ave )
Bonus Experience: Skydeck at Willis Tower (Sears Tower Forever)
We booked timed entry and went up at night—great views, maximum “why am I doing this” energy when you step onto the glass ledge.
📍 Skydeck Chicago (Willis Tower) — 233 S Wacker Dr, Chicago, IL 60606
Skydeck at Willis (Sears) Tower
Dinner: Deep Dish Showdown — Giordano’s vs Pequod’s
Dinner 1: Giordano’s (Stuffed-Style Chicago Staple)
We went classic, leaned into nostalgia, and yes—this is why we budgeted hard all day.
Cost: $37.71 (tax + tip included)
Finish: $4.14 left (Chris beat the budget!)
📍 Giordano’s (Prudential Plaza / Millennium Park) — 130 E Randolph St, Chicago, IL 60601
Dinner 2: Pequod’s (Caramelized Crust Legend)
Pequod’s is the “foodie pick” for a reason: that caramelized crust edge is crunchy, cheesy, and unfairly satisfying. We also split the cheesy bread because we make excellent decisions.
Cost: $41.37 (small pizza + cheesy bread, tax + tip included)
Finish: $2.63 left (Abed barely cleared it, but cleared it!)
📍 Pequod’s Pizza — 2207 N Clybourn Ave, Chicago, IL 60614
Deep Dish Showdown in Chicago
Copy This Itinerary: Tips to Make It Work
Go cheap early (Ann Sather saved the whole budget).
Deep dish is your splurge—plan for it.
Winter hack: schedule indoor breaks (museum, shops, Roastery).
If you’re only doing ONE pizza spot: pick based on your vibe
Want classic stuffed-style? Giordano’s
Want caramelized crust + “best list” energy? Pequod’s
Your turn (comment bait that’s actually fun)
If we do another Cheap Eats episode anywhere except Texas, LA, or NYC… where should we go next—and what’s the one food we have to try?
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Live life one recess at a time. 🙌