Chicago private tours

Chicago invites you to experience its dynamic energy, where the wind off Lake Michigan adds a briskness to your steps along Michigan Avenue. Here, the skyline isn’t just a backdrop; it’s a testament to the city’s ever-evolving story. On a tour with ToursByLocals, the city’s layers unfold before you. Imagine walking the historic Loop, where bygone eras blend with the buzz of today. Dive into a food and wine tour in Lincoln Park, where deep-dish pizza shares the table with culinary finesse. Your guide helps you bypass the queues, taking you into the heart of the Windy City’s soul. Discover speakeasies hidden in plain sight, relive ...

Chicago invites you to experience its dynamic energy, where the wind off Lake Michigan adds a briskness to your steps along Michigan Avenue. Here, the skyline isn’t just a backdrop; it’s a testament to the city’s ever-evolving story. On a tour with ToursByLocals, the city’s layers unfold before you. Imagine walking the historic Loop, where bygone eras blend with the buzz of today. Dive into a food and wine tour in Lincoln Park, where deep-dish pizza shares the table with culinary finesse. Your guide helps you bypass the queues, taking you into the heart of the Windy City’s soul. Discover speakeasies hidden in plain sight, relive tales from the roaring twenties, and see Chicago through the eyes of a local. If you’re looking for more inspiration, take a look at our curated list of things to do in Chicago.

Explore Chicago your way

At ToursByLocals, we believe that how you explore is just as important as where you go. That’s why every Chicago tour is private, flexible, and built around you: Move at your own pace, skip the crowds, make connections and follow your curiosity. Find local guides offering private tours in Chicago for every interest, including:

History tours: Trace the Great Chicago Fire’s footprint at the Chicago Fire Academy site on DeKoven Street, then head to the Stockyards Gate for a window into industrial history. Add Pullman National Historical Park to walk the company town where labour history took shape.

Architecture tours: Step inside the Rookery’s Wright-redesigned lobby, compare the Monadnock’s load-bearing brick with sleek Willis Tower views nearby, and admire Jeanne Gang’s Aqua Tower ripples from the Riverwalk. Your guide can also arrange a private mini-boat cruise for skyline lines without the crowd.

Art and Culture tours: Focus on the Art Institute’s highlights—think Nighthawks and American Gothic—before exploring Pilsen’s murals and a neighbourhood gallery. In Bronzeville, connect music and civil rights at landmarks, then consider an evening set at a classic blues club.

The core is walkable, and CTA trains and buses make cross-town travel simple. For spread-out neighbourhoods, your guide can book chauffeured tours or a private vehicle.

This isn’t a one-size-fits-all itinerary, you can tailor your private tour to match your interests, pace and personality with a local who knows Chicago inside and out.

Walking tours & neighbourhoods

Day trip ideas from Chicago

If you’re based in Chicago, it’s easy to plan day trips to nearby cities and parks that match your interests, and with your tour tailored to food, history, nature, or architecture, you can keep things simple while covering a lot in one day.

Milwaukee, Wisconsin: Head north for lakefront views, a strong brewing heritage, and vibrant neighbourhoods like the Historic Third Ward, and you can spend the day tasting local flavours at the public market, walking the RiverWalk, and digging into architecture or industrial history with your tour shaped around what you like most.

Oak Park, Illinois: Just west of downtown, this suburb packs Prairie School gems and tree-lined streets, and you can stroll past Frank Lloyd Wright–designed homes, learn how the style took root here, and add a quick stop in the charming centre if you want cafés and indie shops woven into your day trip.

Indiana Dunes National Park, Indiana: Trade skyscrapers for sandy ridges, quiet trails, and big Lake Michigan views, and you can hike to shifting dunes, watch for migrating birds, or focus on beach time, with your tour pacing the day to fit kid-friendly walks, photography, or a more challenging climb.

Lake Geneva, Wisconsin: A classic resort town with a walkable shore path, historic mansions, and clear water, and you can circle sections of the lake, pick up local history, or sample small-town eats, while your tour balances scenic viewpoints with time to relax by the pier.

Starved Rock State Park, Illinois: Canyons, sandstone bluffs, and seasonal waterfalls make this a favourite day trip for hikers, and you can follow well-marked trails, look over the Illinois River from high overlooks, and shift the route based on water levels or wildlife sightings.

A private tour with a local guide is the best way to really get to know a place. Skip the crowds, follow your interests, and see a side of Chicago most travellers miss.