Holiday rentals in Chicago

One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!

Standing in front of a camera can be quite intimidating. With experience both in front of and behind the lens, I will always do my best to help you capture the best natural travel photos in the city of Chicago. Worried about how you'll look? Don't be! I will always show you the photos before moving forward. During this experience I will not only help you receive beautiful photos but I will also try to teach you insight about modeling and photography. This experience will be ideal for individuals who are looking for a city tour but would also love to capture some scenic travel and portrait images. I love to build positive connections with others, so this is great for someone who wants to be more engaged and collaborative with their guide. I will be using a Sony DSLR to capture your candid and lifestyle moments. This includes both portraits and full body shots. If you would like to learn more about the editing process or a photographer's guides, let me know and I am more than happy to share my knowledge. You will receive 8 edited images and all unedited photos (usually 200+). Editing does not include body manipulation, but can be requested for an additional charge. If you do not see a time that works for you on the calendar, please send me a message! I do accept large parties! Please note that I cannot guarantee a private session unless you booked as a private session.

On this tour, you'll join me as we explore the city and food culture through the medium of donuts. You'll learn about the history of Chicago, each donut location, how they fit into the larger food scene, as well as try some amazing donuts. We start from Doughnut Vault where we try some of the best donuts you've had in your life. Next we'll stop by Firecakes donuts to try a few of their seasonal flavors. Followed up with Stans Donuts near Michigan avenue and finally, we end at Do-Rite Donuts where they have both delicious donuts and fried chicken (if you want to get nuts at the end of the tour). We look forward to seeing you soon! Other things to note Let us know ahead of time if you have any dietary restrictions (gluten free, vegan, peanut allergy, etc.)

We start with a very popular Chicago dish: the Chicago-style hot dog - which is taken very seriously by locals. Every Chicagoan has their own preference as to how the dog should be made, and you’ll get a chance to try my favorite version. Next up is the world-famous Chicago deep-dish pizza - an entire meal unto itself. I'll take you to a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, we’ll stroll through two classic Chicago establishments. One is a uniquely Midwest phenomenon that is a sight to behold. The other stop is a restaurant born in Chicago and recognized by nearly everyone on earth - but this one is something special. We’ll then continue our tasting journey with a classic Chicago sandwich: Italian beef. You’ll sample this sandwich in a real city institution — no-frills decor included! Finally, it’s time for something sweet inside a truly local hangout. Here, you’ll enjoy a dessert, relax, and purchase a beverage of your choice. Other things to note This tour runs rain or shine, so please dress appropriately for the weather. Personal shopping, additional food and drinks, and gratuity are not included.

We'll meet at my bike loaner HQ in the heart of Chicago's Ukrainian Village where we'll discuss the day's ride and get comfortable riding together. Then, I will lead you on a 4 hour custom bike ride through several Chicago neighborhoods. We'll ride under the historic "L" train, visit several of the city's neighborhoods (historically diverse and modernly hip), get a taste of Chicago's craft beer scene (if requested) and see Chicago's wide range of architectural styles and oddities, 1920s gangster related sites, great skyscraper views, movie locations, cluster of early 1900s movable bridges, and street art. No tour will be the same as it will be adjusted according to your responses to the pre-ride questionnaire. ** I have a small number of older model loaner bikes available for people who do not have one their own. If you prefer to rent newer bikes I can offer some suggestions.** ***As a general rule, unless the next day forecast is for all day thunderstorms, we wait until the morning of to make the final call to cancel. I don't normally cancel the ride if just a shower or two are forecasted. Sometimes we have coordinated with all riders to move the time up or back an hour to avoid bad weather. If a downpour does come during a ride we can wait it out over a snack or a brief look inside a place.*** ****Private groups large than 4 contact me directly. We can set it up.**** Other things to note I highly recommend having a good breakfast before the ride. We can stop anytime for food/drink but it is best to start topped off.