CHICAGO · ILLINOIS
The best of Chicago.
The 15 best vip tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Skip the line at Chicago’s Field Museum. See Sue and Maximo with optional VIP early access and special exhibits, from gems to lions.
Most Popular“I loved it. I will go back every time I visit Chicago. Such beauty and care taken with each exhibit, you could stay all day.”
VIP dinner at Willis Tower’s Skydeck with a made-to-order deep-dish pizza, skyline views, and after-hours access—Chicago at night.
“FANTASTIC - What a good start to our Chicago trip having the whole Skydeck to explore only 3 couples it was wonderful no crushing to see the sights some fantastic photos taken and meal was great saying we were so high up, service was second to none”
A 2-hour minibus tour of the Chicago Loop’s Prohibition-era gangs and ghost stories, with big photo moments and key landmark stops.
“So much fun! I’ve been to Chicago countless times and done several tours and I still learned new things in this tour. Kris was a great guide - entertaining and knowledgeable. Next trip to Chicago with friends or family will include this tour again.”
Smooth O’Hare curbside SUV transfer to downtown Chicago, private for up to 6, with easy SMS pickup and luggage help.
“Driver on time and car very clean”
Private luxury SUV transfer from Chicago Loop to O’Hare with a 10-minute wait, mobile ticket, and professional on-time service.
“Excellent communication and service, politeness and professionalism. Very clean car, with all facilities.”
Private luxury sedan transfer from Chicago Loop to O’Hare with a 10-minute wait, mobile ticket, and pro drivers—priced per vehicle up to 3.
“It was a smooth ride to the airport, especially with the soothing music. The driver was professional and very patient as we checked out the hotel.”
O'Hare to Chicago Loop in a luxury SUV with Inside Meet: SMS driver info, luggage help, and a private one-way ride in about an hour.
“Very good driver and wonderful car. Courtesy and professional. He waited in the arrival hall for almost two hours, because we queued for lost luggage.”
Chicago skyline by minibus and a guided Architecture River Cruise, with stops at Museum Campus and Cloud Gate for $49 in 3.5 hours.
“Great tour, great value for the cost. Wish the bus ride longer than the boat ride. Bout ride heavy focus on architecture. Bus ride spoke on the history of Chicago, much more engaging!”
Private luxury drive to Frank Lloyd Wright’s Oak Park sites from Chicago, with photo stops and easy pickup for up to 3.
“I think the description of this tour is misleading. The entire experience was driving past FLW's houses. We got NO, NONE, NOTHING from our driver. What's the point for $300 I could have taken a Uber for less.”
A 3-hour private VIP Chicago speakeasy tour with secret entrances, preserved Prohibition-era bars, and luxury transport for up to 5.
“Alan, our host, was knowledgeable, kind and funny. He took us to great spots and made everything so fun. It was a huge hit with my group.”
Private O’Hare to downtown Chicago sedan transfer with meet-and-greet, luggage help, and tight communication by text and phone.
“Rosa was GREAT.Our flight was delayed and she patiently waited for us.She was at the baggage carousel with a sign with our name on it.”
4-hour private Chicago sightseeing transfer in a luxury sedan with unlimited stops, wait time, bottled water, and custom routing by Echo Limousine.
“Driver arrived early and confirmed our newly changed itinerary, then helped us out when our planned itinerary didn’t work out. Also pre-planning was excellent for communication with the company.”
Luxury minibus Chicago tour hitting Palmer House, Soldier Field, Museum Campus, Buckingham Fountain, The Bean, and more in 2 hours.
“Great experience! Avery was very knowledgable and had lots of fun facts about Chicago. Saw so many places in a short about of time. Would definitely recommend!”
Private curbside SUV transfer from Chicago Midway to downtown hotels, with 60 minutes free wait, flight tracking, and clear pickup steps.
“Was on time, polite and friendly. Took stretch limo from Midway to Marriott Midtown. Limo was there when our plane landed.”
Private 3-hour Chicago SUV sightseeing for up to 6. Choose your start time and stops, with bottled water and unlimited curbside wait.
“Although our guide was very nice, he was not very knowledgeable about the tour spots. We asked him about various things & he wasn’t familiar with them. We’ve used Viator in the past so we had higher expectations. He was a good driver but not really a guide.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
