We’re here for whatever your interests and style may be. Here’s a few thought-provoking questions to get you started on brainstorming your perfect itinerary. Connect with us if you have any further inquiries or are ready to put plans into action.

How long will your adventure be?

We’re happy to take you around at any time when one of us is available, with increased rates for weekday mid-day excursions. Whether you’re up for a full night on the town or just a couple hours of daytime activities, we’ll make sure you get the most possible out of it.

Still Unsure? Here Are Some Of Our Favorite Itineraries To Inspire You!

North Side Food and Culture Tour

Once you get a few miles north of downtown, Chicago transitions into a collection of some of the most diverse neighborhoods in the country. On this tour we’ll start in Albany Park, a neighborhood with at least two dozen countries’ cultures visibly represented on its streets. Hispanics from across Latin America make up the largest portion of the population, so you’re in the right place to get a mouth-watering taco or try something a bit less ubiquitous like a Salvadoran pupusa or Ecuadorian snacks. Nor can you go wrong with the numerous authentic Middle Eastern, East Asian and even Central Asian options (ever tried Kyrgyz food?).

We can get to our next destination however you’d like, but a nice bike trail could take us there for a great way to burn a few of the calories you just added. We’re headed next to Devon Avenue, something akin to Albany Park’s diverse vibe but with Indians, Pakistanis and other South Asians being the predominant presence. The sweets, samosas and more that people from across Chicagoland travel to buy serve as great finger food, but can nonetheless be deceivingly filling. Muslims, Hindus, Christians, Jews and Sikhs all have houses of worship in or around a short stretch of Devon, creating a bustling but impressively harmonious environment.

We then head east nearly arriving at the lake, in the aptly named neighborhood of Edgewater. A number of Ethiopian joints line the streets, with great coffee or their own twist on samosas if you can only handle a bite. We finish by walking a short way to “Asia on Argyle”, a sort of micro neighborhood within the wider neighborhood of Uptown that is known for its longstanding Vietnamese character in particular.

South Side Food and Culture Tour

We begin our tour in Chicago’s Chinatown, which has been thriving in recent years with a growing population and attractiveness as a local destination. Here you can eat Chinese dishes that haven’t quite hit mainstream American culture due to their spice level or unique meat cuts, but are delectable and unquestionably authentic.

Next we’ll travel a bit south to Bronzeville, which has the longest-running Black cultural history of any neighborhood in the city. Award-winning soul food spots grace the area, and more recent immigrants have delivered on some fantastic West African cuisine. You’ll learn about the various phases of building up, tearing down and building back up again that Bronzeville has been through, and the promising endeavors currently occurring to strengthen the community.

Next we cross the highway westwards to the neighborhood of Bridgeport, which is at an interesting confluence of European, East Asian and Hispanic cultures. Its food scene reflects the area’s diversity, with both unexpected fusion combinations and simple authentic spots that locals will go to war to defend. Bridgeport has long been home to many of the city’s not so squeaky clean political class, and we’re happy to tell you all the dirty secrets we know.

Our last stop takes us farther west to Chicago’s approximate geographic center in Mckinley Park, a tight-knit working-class community containing a huge park by the same name. While the population is similarly diverse to Bridgeport, Mexican delights are probably the top priority on the menu around here. There’s a whole lot to learn about from the neighborhood’s history, from the successes of community crime prevention methods to ongoing issues of environmental injustice.

West Side Parks Tour

In the years after its significant destruction in the Great Fire of 1871, Chicago boomed yet again. Many innovative thinkers and planners took advantage of such a rapidly growing urban space by designing the expansions to be highly livable for the standards of the time.

One of the highlights of these intentions is the so-called Emerald Ribbon, a network of parks making a ring through the city that are largely connected by greenways on boulevards. While these greenways were not totally finished and the eventual plans for the city were far more ambitious than what materialized, three huge parks on the West Side do indeed connect to one another through bikeable routes. Each has a magnificent presence that bears a non-coincidental resemblance to New York’s Central Park, as landscape architect Frederick Law Olmsted designed all four parks.

We’ll start with Humboldt Park, which today is at the epicenter of Chicago’s rich Puerto Rican culture. Whether you want to visit the Puerto Rican National Museum that lies within the park or just chat up some local shop owners, there’s plenty of ways to get some cultural immersion around here. Next we hit Garfield Park, which has beautiful foliage and a lagoon but is probably better known for its indoor space - the incredible Garfield Park Conservatory holds several biomes worth of plant species and is free to visit. We continue southeast to Douglass Park, where you’ll find great athletic facilities and even a mini golf course. You’ll learn some of the complex modern issues with regards to this park, such as controversies around the annual Riot Fest music festival being located here. If you’re hungry, we can make the quick hop to a greasy hot dog spot or somewhere in Little Village to finish the tour in the heart of Chicago’s Mexican-American culture.