Chicago: Loop Food Tour with Deep Dish Pizza & Beef Sandwich

Summary

Deep dish pizza bites, Italian beef, and city stories in the Loop

You’ll wander through Chicago’s Loop district tasting deep dish pizza, classic Italian beef sandwiches, gourmet popcorn, and a surprise “secret dish.” With a local foodie guide leading you through iconic buildings like the Rookery and Palmer House Hilton, you’ll soak up flavors and city stories that linger long after you leave.

What’s the experience like?

The tour kicked off right in the middle of the Chicago Loop — I could still smell roasted coffee drifting out from somewhere as our guide, Marcus, waved us over. He had this way of making you feel like an old friend within five minutes. First stop: deep dish pizza. The cheese was so gooey it nearly slid off my fork, and I swear the tomato sauce tasted brighter than any pizza I've had back home. Someone in our group asked if real Chicagoans actually eat this much cheese and Marcus just grinned — “Only when we’re showing off.”

Walking down LaSalle Street felt like being swallowed by glass and stone canyons. The Board of Trade building loomed at the end — all sharp lines and that weird hush you only get downtown on a weekend. We ducked into a place for Italian beef sandwiches next; I tried not to get jus all over my shirt (failed). The bread was softer than I expected, soaking up everything, and there was this vinegary snap from the peppers that surprised me. Marcus told us how these recipes go back generations — he even pointed out a spot his uncle used to work at nearby. At some point I realized I was full but kept eating anyway.

I didn’t expect to care about architecture but standing under the Rookery’s ironwork ceiling made me pause longer than I thought I would. Light bounced around in odd ways — gold on marble, shadows in corners. There were stories about fires and rebuilding and how Chicagoans never really quit anything (except maybe diets). Somewhere between bites of fudgy brownie at Palmer House Hilton and trying to guess what the “secret dish” would be (I won’t spoil it), someone started laughing about how we’d all need naps after this much food.

By the end I’d stopped checking my phone for messages — just kind of listened to people swap stories about their own cities or ask Marcus about his favorite hot dog stand (“Don’t trust anyone who puts ketchup on it,” he warned). Walking back through Federal Plaza with popcorn in hand, city noise echoing off glass, I caught myself thinking how places taste different when someone local shows you around. Still think about that sandwich sometimes.

Step-by-step itinerary

Day 1 — Chicago Loop District Food and Architecture Tour

• Visit African American Mayor memorial
• Walk LaSalle Street economic corridor
• See Calder stabile at Federal Plaza
• View Willis Tower exterior
• Explore Rookery Building architecture
• Discover Palmer House Hilton history

Top questions

How long is the Chicago Loop food tour?

The tour covers several stops within walking distance in the Chicago Loop district; exact duration may vary based on group pace.

Is lunch included on this Chicago food tour?

Yes, multiple tastings are included such as deep dish pizza, Italian beef sandwich, hot dog, brownie, popcorn, plus a secret dish.

Does this tour include visiting famous buildings?

Yes, you'll see landmarks like the Rookery Building and Palmer House Hilton along the route.

Is there a vegetarian option available?

You should contact the operator in advance to discuss dietary requirements so they can try to accommodate you.

How much walking is involved on this food tour?

The tour involves a fair amount of walking through downtown; comfortable shoes are recommended.

Are drinks included during the tastings?

The inclusions focus on food items; drinks are not specifically mentioned as part of the tastings.

What is the secret dish on this Chicago food tour?

The secret dish is revealed only on the day of your tour—it's part of the fun!

Can people with limited mobility join this tour?

This experience involves walking; those with mobility concerns should check with organizers before booking.

What’s included

Your day includes guided walks through downtown Chicago’s Loop district with stops for deep dish pizza with sausage, an Italian beef sandwich dripping with jus, classic Chicago-style hot dog, gourmet popcorn from a local spot, rich fudgy brownie at Palmer House Hilton—and one delicious secret dish revealed during your visit.