Chicago · PRIVATE
Every trip has one free afternoon too few. These 15 private tours justify the slot, priced and timed so you can decide in minutes and get back to the fun part.
Explore the Art Institute of Chicago with a private guide, skip-the-line entry, major masterpieces, art stories, and a flexible 2.5-hour route.
“Got a great macro and micro view of the Art Institute with our trusty guide Heath. It was perfect in pace, depth, and tone.”
Explore Chicago by private vehicle with hotel pickup, guided stops at Millennium Park, Wrigley Field, Hyde Park, and more.
“Scott is very knowledgeable, eloquent, and keep you interested throughout the driving in the streets of Chicago. He will tell you stories that will blow up your mind.”
Review of Carmel’s private Chicago airport transfer from O’Hare or Midway, with vehicle choices, pricing, pickup tips, and honest drawbacks.
“We were dropped off the wrong hotel, Lee then had to walk in the dark unfamiliar with the area to find our hotel with our luggage”
Tour Chicago’s Art Institute with a small group, skip the main line, and see Impressionist masterpieces with an expert guide.
“Mandy was an extremely knowledgeable and excellent tour guide. Would definitely recommend her and wish we could do it again!”
See Chicago from a private helicopter, from Wrigley Field and The Bean to Lake Michigan, with a 45-minute flight from Schaumburg.
“Pilot cancelled one hour prior to our scheduled time. While I appreciate his concern for our safety. I was on the Uber already from the city (Chicago). The Uber driver was lovely but $200 for a ride in an Uber was not the helicopter over the city experience I was expecting. I do need to note he offered to reschedule but due to the fact I have other plans and I’m on a vacation for my Birthday my time was extremely limited. I was given a refund but my dissatisfaction and disappointment was an understatement.”
Walk Chicago’s architectural core from the Chicago Theatre to Cloud Gate, with local stories, Pedway access, train fare, and tastings.
“Great walking tour, learnt many facts & tasted some local treats. Rich was a great guide, we were even treated to his rendition of a couple of songs & some music to walk the Pedway!!! Highly recommend”
A practical review of Chicago airport transfers to ORD and MDW, with honest advice on timing, vehicle choices, luggage, service, and value.
“This was our first experience with this operator and we were very pleased with the service provided. The support was very efficient, always responded promptly, and communication was excellent. Our driver, Antwone, was a special case. An excellent professional, he assisted us upon arrival and also on the day of departure. Attentive, efficient in meeting our schedules and safe driving. A professional who truly deserves five stars in his rating.”
See Chicago’s greatest artworks on a private, flexible Art Institute tour with skip-the-line entry, expert guidance, and all-day museum access.
“Best way to experience the Art Institute of Chicago. So much to see and do, it’s always best to rely on an expert. Joel provided us with all the highlights, including the behind the scenes insights like how the piece was acquired. That allows you to truly experience and appreciate the art. Bonus your ticket is good all day, leave for lunch and come back to experience more at your leisure.”
Sail privately from Navy Pier for Chicago skyline views, flexible routes, Bluetooth music, and a relaxed two-hour Lake Michigan outing.
“Mike was awesome! A beautiful experience on Lake Michigan! Thank you for being a great captain! Would definitely do again.”
Taste Chicago classics, from deep dish to Italian beef, while walking the Loop with a private local guide and city history.
“Need to walk and be hungry. This was an awesome combination of history of Chicago food but all history.”
Private MDW to downtown Chicago transfer with flight tracking, luggage help, and a 30 to 60 minute ride, but vehicle quality can vary.
“Driver was on time, communicated in advance and was conscientious. Pleasant, professional, and caring.”
Explore Chicago architecture, underground walkways, Riverwalk views, deep-dish pizza, hot dogs, and more on a five-hour private tour.
“I thought this tour was fantastic. Our guide Dash was hands down the best tour guide I've ever had. He filled the 3 hour architecture part of tour with a bunch of wonderful spots and was extremely knowledgeable of every aspect of all of them. I felt like he could have easily dRead more”
Review of Elife Ride’s private ORD to Chicago transfer, with flight tracking, luggage help, air conditioning, pricing, and booking tips.
“Thank you for great service! The drive to my hotel was smooth! A great start for my first time in Chicago!”
Shape a private Chicago walking tour around architecture, art, food, or history, with a local guide and stops across downtown.
“Our guide Dave reached out prior to learn about what we wanted to do and see. He timely met us at our hotel and gave us a GREAT tour of downtown Chicago including lots of history, facts and places we had not considered including the Read more”
Explore Chicago with a private local guide, flexible walking routes, landmark views, museum planning, and useful city advice.
“El Guia tenia buena voluntad, pero falto de motivacion, iniciativa y conocimientos...esperabamos algo mas que un paseo con poco contenido de historia y anecdotas...”
Keep browsing
Pick a deck, a tower or a table.
