Written by and photos by Nadia Ibanez

I never used to be one who would attack a brand new city with a bunch of touristy things. But when you’re trying to tackle a city like Chicago in just a few days, sometimes you just gotta sign up for a tour and go along for the ride. During my trip to the Windy City, I went on a handful of Chicago tours both within the downtown area and beyond.

From tame architecture and history tours, to sexy red light district tours, here’s a list of some of the Chicago tours you can go on while exploring this amazingly beautiful city.

Historic Chicago Walking Bar Tour with Chicago Detours

History lessons have never been my strong suit. I have trouble listening to someone chatter about history while I’m in a new city, let alone a classroom, because I’m busy looking around at all of the sights. But, Chicago Detours is a company you want to get to know if you’re seeking a Chicago history lesson with some booze and bites.

We started our tour at the Tribune Tower and the Intercontinental Hotel where we learned a brief history of the city, who helped to build commerce in the area, what industries fared well during growth, and more. After wandering the streets and learning more about the secret life of drinkers and booze during the prohibition era, we stepped inside the original Billy Goat Tavern.

Any old school Saturday Night Live fan will immediately yell, “Cheezborger, Cheezborger! No Pepsi…Coke!” in their heads upon hearing about this pit stop. The Billy Goat Tavern was definitely my favorite stop on this tour mostly because of the people watching, the fantastic bar and bartenders, historic memorabilia all over the walls, and of course, the cheeseburgers.

By the time the tour was over, not only did we learn about how booze shaped the city in nearly every decade, but we also boozed at every stop. From beers at Billy Goat, to wine and appetizers at the Tortoise Club and a historic mansion, we experienced the booze culture in nearly every way imaginable.

Pizza & Cocktails Tour with Chicago Pizza Tours

Pizza and booze in Chicago is like peanut butter and jelly to the rest of the country; it just goes together and there’s no explanation. Chicago’s deep dish pizza is globally famous and I had to get my hands on all of the pizza I could. If you’re in town for a short period of time and want to try all of the famous pizza spots in the area, I highly recommend booking a Pizza & Cocktails Tour with Chicago Pizza Tours.

Our group met at Flo & Santos, a thin-crust pizza spot favorited by local Chicagoans. We ordered up some cocktails and local brews while our table was flooded with huge thin-crust pizzas with toppings inspired by local tastes. The Flo’s Polish was topped with Polish Kielbasa, sauerkraut and bacon, while Marco’s Italian Beef was topped with shaved beef, giardiniera, caramelized onion and roasted tomatoes. We all shared our stories and what brought us to Chicago, before we headed to the next joint.

Throughout the evening, we stopped by Pizzeria Serio in the Lakeview neighborhood for Neapolitan-style pizza, the famous Lou Malnati’s in the Gold Coast neighborhood for a taste of history, and Pizano’s for Oprah’s favorite deep dish and dessert. The drinks continued to flow throughout the night and we all naturally befriended each other by the end of the tour.

If you’re traveling solo, this tour is perfect for you. There’s nothing like a few too many gin and tonics to open up even the most timid of travelers. The pizza was all fantastic and I totally get why people have Chicago pizza shipped to their homes after visiting these spots. Not only do you get a taste of Chicago history on these tours, but you also get a sense of why this city attracts all walks of life.

Lincoln Park Food Tour with Chicago Food Planet

I’m always one to try and discover hip and up-and-coming neighborhoods while traveling and I had been hearing a lot about Lincoln Park. Located about 20 minutes outside of the Chicago Loop and downtown area, Lincoln Park is an adorable neighborhood offering culture, historical sights, delicious food, shopping and more.

I signed up for the two-hour Lincoln Park Food Tour with Chicago Food Planet, which specializes in walking tours of Chicago’s best neighborhoods outside of heavily-touristed areas. This tour company takes guests around Chicago’s neighborhoods while educating travelers about how the local food culture came to be and how artists, immigrants, students, professionals, and everyone else has shaped the area.

Deemed one of Chicago’s most diverse and largest neighborhoods, we learned all about Lincoln Park’s history with our tour guide, Jackie. We heard about the area’s history and people, while tasting specialty, locally-made items like popcorn, cupcakes, bagels, luxury chocolate and stuffed pizza. (PS: The pizza from Bacino’s was out of this world!) Lincoln Park is a great city for eating, drinking and shopping so if you feel like you’ve tackled downtown Chicago and want a glimpse into the ‘burbs, make sure to add this neighborhood to your list.

Chicago Food Planet operates tours in other parts of town, including the Gold Coast, Old Town, Bucktown, Wicker Park and Chinatown. Our guide, Jackie, was absolutely lovely and super smart and we couldn’t have asked for a better guide. If you fall in love with one of the stops on the tour, Chicago Food Planet offers discounts at the shops or restaurants for purchases after the trip concludes.

Red Light District Tour with Weird Chicago

If you really want to see a part of Chicago with the perfect blend of grit, boozy history and scandal, check out Weird Chicago tours immediately. This tour brought some light into the sex and kink scene of today and the bygone era. Fancy a trip to a sex dungeon? Ever wanted to meet a man who custom manufactures bustiers and thigh-high leather boots? Or, do you need to freshen up your education on today’s sex toys? Then look no further than the Red Light District Sex Tour.

This Chicago tour is a bit difficult to put into words, especially if you’re tame at heart, because the intel that I gathered on this trip would make anyone blush. Join the group as an open-minded individual, with your friends, or significant other. And be prepared for some silly, while also incredibly intriguing, narration. Let’s just say that by the time the tour was over, I found myself in a swing in the middle of a sex dungeon, tried on some vintage-inspired bustiers, and got a glance into electro-magnetic stimulation at a sex shop.

I guarantee you’ll end the night all hot and bothered with a new wealth of information about the Chicago local sex industry. But if sex dungeons and toys aren’t totally your thing, Weird Chicago also offers tours about the city’s ghosts, criminal history, gangsters and “Murder Castle.”

Architecture Tour with Shoreline Sightseeing

If you’re looking for a relaxing Chicago tour of the downtown area’s architecture and skyscrapers, I suggest an Architecture Tour with Shoreline Sightseeing. This 75 minute tour, great for those in a time crunch, takes you down the Chicago River and among the most notable towers and skyscrapers. You’ll learn about the engineering of these buildings, who made them, who occupies the space now, and so much more. Ever wondered about the uniquely-shaped round parking structure in the middle of the Loop, or the Aqua high rise apartment building that mimics the image of waves when viewed from atop each balcony? Or the history behind the champagne-bottle shaped Carbide & Carbon building? You’ll learn all about these landmarks and more on this tour.

I hopped on the Architecture River Tour, which launches off from two different locations, and we saw more than 40 different, distinctly Chicago landmarks. I highly recommend going on the tour right around sunset, or at least while the sun is out, as the boat is uncovered and offers amazing views.

Design your own Self-Guided Tour at the Art Institute

The Chicago Art Institute tops everyone’s list of must-see places but with almost a million square feet of explorable space, the idea of seeing everything can be daunting. From modern art and photography, to marble sculptures and Picassos, there’s something here for everyone. I only had a few hours to spend at the Art Institute and luckily there were a few options to help maximize my time.

Before you visit, check out the website’s section for themed mini tours. Or, download the Art Institute app or opt for an audio guide. Whatever your speed, you’ll find a ton of interesting exhibits.

Editor’s Note: Thank you to ALL of the tour companies who allowed me to join your group outings! Thank you for your generosity and hospitality. See you soon!