Chicago: Private Food Tour with Deep Dish & Beef Sandwich

Deep dish pizza bites, Loop architecture walks, local stories & secret snacks

You’ll taste real Chicago: deep dish pizza straight from the oven, gooey Italian beef sandwiches, classic hot dogs, and a few surprises along the way. With a local foodie as your guide through the Loop’s famous architecture and hidden corners, you’ll laugh, eat too much popcorn, and maybe learn to love fudge brownies for more than just dessert.

Step-by-step itinerary

Day 1 — Chicago architecture and food tour

• Visit African American Mayor memorial
• Walk LaSalle Street financial district
• See Calder's Federal Plaza stabile
• View Willis Tower exterior
• Explore Rookery Building interior
• Tour Palmer House Hilton
• Taste deep dish pizza
• Try Italian beef sandwich
• Enjoy gourmet popcorn
• Discover secret dish

The Experience

I’ll be honest — I booked this private Chicago food tour mostly for the deep dish. But walking into the Loop with our guide (her name was Jamie, born-and-raised South Sider), I felt this weird mix of excitement and nostalgia even though it was my first time here. The city just hums — you get these quick bursts of wind between buildings and the smell of hot dogs drifting out from somewhere I couldn’t see yet. Jamie started us off with a story about Palmer House Hilton that made me laugh; apparently it’s all romance and fudge brownies in there. I didn’t expect to care about a hotel but… well, I do now.

We stopped for pizza next — proper Chicago deep dish, sausage bubbling under a thick layer of cheese. It’s heavier than it looks. Jamie showed us how to eat it without making a mess (I failed anyway). Then we walked past the Rookery Building; she pointed out the Frank Lloyd Wright staircase inside, which I never would’ve noticed on my own. There’s something about eating while you walk that makes you pay attention differently. The air smelled like popcorn at one point — turns out that was our next stop. Sweet, salty, crunchy; honestly, gourmet popcorn is underrated.

The Italian beef sandwich surprised me most. It’s messy and juicy and you have to lean over your plate or risk dripping everywhere (I did both). Somewhere along LaSalle Street, Jamie told us about the Board of Trade building and those traders in wild jackets — she mimed their hand signals and got us all laughing. We finished with a “secret dish” I’m not supposed to spoil, but let’s just say I’m still thinking about it days later. Walking back through those canyons of glass and steel felt different after all that food — slower maybe? Or maybe just full.

Top questions

How long does the private Chicago food tour last?

The tour typically lasts several hours as you walk through the Loop district sampling various foods.

Is lunch included on this Chicago food tour?

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

Are there vegetarian options available?

You should contact in advance for dietary requirements so they can accommodate your needs as best as possible.

Does this Chicago food tour include pickup?

No hotel pickup is included but public transportation options are nearby for easy access to the starting point.

What should I wear or bring?

Comfortable shoes are recommended since there is a fair amount of walking involved during the tour.

Is this private tour suitable for families?

The tour is suitable for all fitness levels but infants must sit on an adult’s lap; check if young kids will enjoy all tastings.

Which neighborhoods or landmarks will we see?

You’ll explore Chicago’s Loop district with stops near Palmer House Hilton and Rookery Building among other architectural highlights.

Can I book flexible start times for this private tour?

Yes—private tours offer more flexibility with start times and dates compared to group tours.

What’s included

Your day includes guided tastings of deep dish pizza with sausage, Italian beef sandwich, classic hot dog, gourmet popcorn, a fudgy brownie at Palmer House Hilton (yes—the original), plus one secret dish revealed on the day. You’ll be led by a local foodie guide through Chicago’s Loop district with plenty of stories along the way; just bring comfy shoes and an appetite.