Sometimes you just need a woman’s insight. When it comes to travel, a female perspective can direct you to things you might never have noticed. Like the colors on a building or faces carved into cornices. Or perhaps the tastes of a city in food & drink and attitude.
Discover Chicago's Top Woman Run Tours
From award-winning art and architecture to graft and power, gangsters and dive bars, steakhouses and haute cuisine—Chicago has it all. In this time when social distancing and small groups have changed the dynamic of travel, we have these six ladies to thank for harnessing their passion for Chicago and curating experiences to safely enjoy the “City by the Lake” whether you’re a first-time visitor or a local with a penchant for wanderlust. Health protocols are stated in advance. Masks and hand sanitizers are provided if you don’t have your own. So, gear up and get out. Chicago is open.
These Birks are Made for Walkin’
The Windy City invites walking especially when it’s not so chilly outside. In a city known for having some of the country’s most striking skyscrapers as well as great food, a beautiful waterside and friendly people, a walking tour lets you stop, look around and absorb the nuances at a leisurely pace.
Inside Chicago Walking Tours wants you to “get lost in the details,” notes founder and guide Hillary Marzec. On these small-group, architecture-focused strolls you’re encouraged to see the city inside and out as you explore on two feet. Hillary is a master of pointing out the unusual – she’s spent many years as a Chicago tour guide and can riff on the unexpected, a talent perfected from years as a comedy and improv performer. Two Saturday itineraries include a tour of Chicago’s stunning interiors and a “then and now” program where you’ll view historic photos and “time travel” to the locales where they were shot. If you’re a fan of art deco, Frank Lloyd Wright and public art, these tours are for you.
Scheduling both virtual and IRL history and architecture walking tours, Chicago Detours reveals a more personal side of Chicago. “Our tours talk about the psychology of design and the people behind the buildings. We have a story-telling approach to creating the tours,” explains Amanda Scotese, founder. Amanda is the right candidate to do this. With years under her belt as a tour guide in Europe and her intense love affair with Chicago, she is passionate about showing off the city’s most important landmarks as well as personal finds. The currently offered interior architecture tours are available for private groups of up to ten guests and detour to insider-y locales and shortcuts.
Private walking tours with a food component are offered by former reporter Leentje De Leeuw’s CHICA-GO for families and “small bubbles” of six people or less. Three itineraries with at least one tasting stop meander through the ethnically diverse Historic Pilsen District (Chicago’s West Side) and the West Loop, or on a personalized route with additional food and drink possibilities. This is your chance to try an iconic Chicago hot dog or Chicago deep-dish pizza, or sample the Mexican cuisine notable in Pilsen. Tours are available in English, Dutch and French.
A City Designed for Photographers
Tour Through a Lens offers a photographic immersion of Chicago with a mix of on-foot and transit time. Led by accomplished photographer Teresa Peek, the one-on-one bespoke experience is designed for your goals and interests and can last three to nine hours. Tours range from a “one focus” tour to learn creativity and composition skills with your camera or smartphone or concentrate on one area of the city, to an expansive local’s experience that includes capturing views from trains bookended by sunrise or sunset. These niche tours are as socially distanced as you can get—there’s just you and your guide.
Crafted for Adults Only (Mostly)
Liz Garabay leads explorations of Chicago through a different lens, “the lens of alcohol.” A historian enamored with tavern culture and the legacy of beer, Liz explores the character of the city through its history of speakeasies and pubs. History on Tap itineraries show you how booze and beer shaped Chicago and vary depending on guest preferences and what’s topical. Liz is a font of information having worked at the Chicago History Museum. Given the nature of the tours and the inclusion of several watering holes, only adults may participate.
Are you ready for some serious laughs? Chicago Elevated was created by ex-Second City Comedy Club performer Margaret Hicks adhering to a theme of “Tours So Fun, You Just Might Learn Something.” With enough irreverent commentary, eccentricity and fact-filled improvisation to make you understand their mainly adults-only designation, tours with names like “Disaster!”, “My Favorite Things” and “The UN-tour” encourage you to look up, around and underneath as you explore the characters and culture of Chi-Town. A one-of-a-kind Pedway tour is planned as soon as buildings fully open.
I’ll Do It My Way
If organized tours aren’t your thing, City Catt, founded by mompreneur Lizia Santos, will connect you to an on-the-ground Chicago expert who will develop an itinerary perfect for you and your family. Whether you’re craving a foodie or theater-filled sojourn, traveling in a multi-generational bubble, or looking for a staycation experience with wide open spaces, these knowledgeable ladies will craft your perfect Windy City self-guided adventure.