5 of the Best Chicago Private Tours


There are a wide choice of guided tours of Chicago that provide a unique perspective on the city, including several private tours for select groups of families or friends.

(Photo: Guydeez / Courtesy GetYourGuide)

If you like the idea of exploring the Windy City in the company of an expert guide, but would rather avoid doing so as part of a larger group, then there are a wide number of private tours available. These take place in small groups of 1 to 6 friends or family and, though you’ll need to pay for the privilege, it does ensure a degree of intimacy and exclusivity that will make the experience all the more special. Here are five of the best Chicago private tours currently on offer.

Custom tour with a local guide

In a city that can sometimes feel a little inaccessible to outsiders, this tour offers the chance to see Chicago through the eyes of a an expert private guide. Fully customisable to span between two and eight hours, tours can be planned beforehand around your specific areas of interest so you can get a deeper insight into the city and its characteristics that most appeal to your preferences and tastes. For maximum convenience, your guide can meet you at your hotel or other accommodation if you wish. Tickets to any attractions you want to visit  are not included. From $54 per person.

Book at GetYourGuide

Helicopter Tour of Chicago Skyline

(Photo: Paratus Air / Courtesy GetYourGuide)

Chicago is a captivating vision from any vantage point, but perhaps nowhere more so than up high in the air where the majestic cityscape can be seen in fully panoramic glory. This daytime helicopter tour offers this  very opportunity, whisking you and up to five other private guests above the city during a 10 or 20-minute flight, depending on which you chose.  As you soar through the sky, you’ll get to marvel at the Chicago skyline and capture photos of landmarks like Willis Tower and Navy Pier, while your pilot provides live commentary on what’s below. Noise cancelling headsets plus access to the customer experience centre and helicopter lounge are included. From $187 per person.

Book at GetYourGuide

Speakeasy Pub Crawl in Chicago with Local Historian

A rather more civilised and culturally enriching experience than a traditional pub crawl, this tour transports visitors back to 1920s prohibition era Chicago, when unlawful speakeasies were commonplace at a time when alcohol was banned across the city. During the 3-hour private tour for two people, you’ll be led by your guide – a local historian dressed in period costume – will lead you through secret entrances to speakeasies once frequented by such notorious figures as the gangster Al Capone. Once ensconced in these historic watering hole, you’ll get to listen to the colourful stories behind the prohibition era and even sample a cocktail of choice for many of its infamous patrons of yesteryear. Hotel pick-up and drop-off are included. From $896 per group (max 2 people)

Book at Viator

Foodie Tour: Windy City Favs

(Photo: ForeverVacation / Courtesy GetYourGuide)

The rich and diverse food culture of Chicago can be explored on this half-day tour that includes plenty of food samples along the way. Accompanied by a guide well versed in the city’s culinary culture, you and your private group will visit some of Chicago’s most famous eateries and popular local food haunts. From the famous deep dish Chicago town pizza to authentic Italian cuisine, you’ll get to try a full spread of tantalising treats that showcase the city’s vibrant food scene. All food tastings plus mineral water are included. From $187 per person.

Book at GetYourGuide

Sunset Sail on Lake Michigan 

Choose your route and even your onboard tunes during this fully customisable two-hour sailing tour that treats you to jaw-dropping views of Lake Michigan and the Chicago skyline.  As part of a private group of up to 5 guests, you’ll even have access to a refrigerator well stocked with drinks and snacks for you to enjoy as you cruise along the scenic waters off the Chicago coastline. To make the experience extra memorable, tours can be timed to coincide with sunset. From $553 per group (max 6 people)

Book at Viator

By Paul Joseph