Chicago · VIP

The 15 VIP Experiences in Chicago That Earn Their Price

16 tours  ·  from $29

Every trip has one free day too few. These 15 vip experiences justify the slot, priced and timed so you can decide in minutes and get back to the fun part.

Chicago: Field Museum of Natural History Ticket or VIP Tour - What the Early Access VIP Tour adds
Chicago History Tours, Field Museum Tickets, Historical Tours, Museums, Tickets, Tour Reviews, Tours, VIP

Chicago: Field Museum of Natural History Ticket or VIP Tour

1.Field Museum of Natural History Ticket or VIP Tour

★★★★★★★★★★4.7 · 717 reviews · 1 day · from $29Our pick

Spend a full day at Chicago’s Field Museum with general admission, a Discovery Pass, All-Access Pass, or Early Access VIP Tour. See Sue, Maximo, the Lions of Tsavo, ancient artifacts, gems, and a full-size mastaba tomb. The VIP option includes a one-hour docent-led dinosaur tour for up to 20 people.

“It is an impressive museum and the people working there were friendly and helpful.”

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Skydeck Chicago: Pie in the Sky VIP Dinner at Willis Tower - Reaching the Skydeck and finding the right entrance
Chicago Dinner Cruises, Dining Experiences, Dinner Experiences, Tour Reviews, VIP, Willis Tower Skydeck Tickets

Skydeck Chicago: Pie in the Sky VIP Dinner at Willis Tower

2.Skydeck Chicago: Pie in the Sky VIP Dinner at Willis Tower

★★★★★★★★★★3.5 · 44 reviews · 2 hours (approx.) · from $154

You’ll ride to the 103rd floor of Willis Tower after public hours, settle at a table overlooking Chicago, and enjoy a custom three-course Giordano’s meal. Choose up to six pizza toppings, a salad, dessert, and a soft drink, then explore the Skydeck and glass Ledge before heading back down.

“I would highly recommend the Skydeck Dinner on the Ledge. It was the perfect location for me to propose to my future wife. Our waiter was very attentive and happily took many pictures plus a video of the proposal. These are memories we will cherish for the rest of our lives. Thank you for the unforgettable evening!”

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Chicago Gangsters and Ghosts Luxury Minibus Tour - Holy Name Cathedral and a Prohibition-era shooting
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Chicago Gangsters and Ghosts Luxury Minibus Tour

3.Chicago Gangsters and Ghosts Luxury Minibus Tour

★★★★★★★★★★5.0 · 33 reviews · from $49Top rated

Ride through Chicago’s Loop with guides such as Alan, Ty, Matthew, Avery, Karina, and Kris, hearing Prohibition tales and ghost stories. You’ll see Holy Name Cathedral, Frank Nitti’s vault, Death Alley, the Congress Hotel, and Al Capone’s former speakeasy site during this two-hour bus tour.

“Our guide Ty was knowledgeable and entertaining. Of the three tours we took during our trip this one gave us locations we wanted to revisit. We look forward to revisiting Chicago and taking this tour again. I recommend this tour to all.”

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O'Hare Airport Transfer to Chicago, Curbside - Luxury SUV - What the private SUV ride is like
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O’Hare Airport Transfer to Chicago, Curbside – Luxury SUV

4.O’Hare Airport Transfer to Chicago, Curbside – Luxury SUV

★★★★★★★★★★5.0 · 19 reviews · 30 minutes to 1 hour (approx.)

Book a private luxury SUV from O'Hare to your Chicago address for up to six people. After landing, you receive the driver's details by text, collect your bags, and meet the car at the curb. The ride usually takes 30 minutes to one hour, depending on traffic.

“Excellent service, on time, clean, very professional driver and safe. Very pleased. Will be using the service again.”

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Chicago Airport Transfer to O'Hare & Midway Airport - Luxury SUV - Why the luxury SUV can be worth the $155 price
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Chicago Airport Transfer to O’Hare & Midway Airport – Luxury SUV

5.Chicago Airport Transfer to O’Hare & Midway Airport – Luxury SUV

★★★★★★★★★★5.0 · 15 reviews · 30 minutes to 1 hour (approx.)

Book a private luxury SUV from Chicago’s Loop to O’Hare, with service available around the clock. The ride takes about 30 minutes to an hour, depending on traffic. Echo Limousine provides a clean vehicle, 10 minutes of complimentary wait time, and an upper-level airport drop-off.

“Excellent communication and service, politeness and professionalism. Very clean car, with all facilities.”

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Chicago Airport Transfer to O'Hare & Midway - Luxury Sedan - What the pickup feels like in practical terms
Airport Transfers, Chicago Private Car Transfers, Midway Airport Transfers, O'Hare Airport Transfers, Private Drivers, Tour Reviews, VIP

Chicago Airport Transfer to O’Hare & Midway – Luxury Sedan

6.Chicago Airport Transfer to O’Hare & Midway – Luxury Sedan

★★★★★★★★★★5.0 · 12 reviews · 30 minutes to 1 hour (approx.)

Book a private luxury sedan from Chicago’s Loop to O’Hare for up to three people. You choose the pickup time, ride without strangers, and receive a 10-minute wait allowance. Drivers such as Dee, Alfredo, Rosa, and Franklin have earned praise for clean cars and courteous service.

“We had a wonderful experience! We went to and from O’Hare over the holidays visiting family. Both drivers were professional and the drive was relaxing. Dee was our driver going back to the airport, she was fantastic, friendly and funny! We will definitely use this car service again. Oh and did I mention the price was on point!”

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O'Hare Airport Transfer to Chicago with Inside Meet - Luxury SUV - The private luxury SUV ride into Chicago
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O’Hare Airport Transfer to Chicago with Inside Meet – Luxury SUV

7.O’Hare Airport Transfer to Chicago with Inside Meet – Luxury SUV

★★★★★★★★★★4.5 · 11 reviews · 30 minutes to 1 hour (approx.)

Meet your Echo Limousine driver at O’Hare baggage claim, get help with your bags, and ride privately to the Chicago Loop in a luxury SUV. The $200 rate covers up to six people, gratuity, parking, taxes, and bottled water. Allow 30 to 60 minutes, depending on traffic.

“We were told to go to the outside lane after we picked up our luggage which we did. THe driver was waiting for us by baggage claim which I did not realize. He was rude and blamed us for not being in the correct place. I had texted him so he knew where we were located. Then he had us WALK for another 20 minutes to where he had parked the car in the parking garage. The driver continued to complain about us the whole time we were hauling our luggage all over the place. He was very rude and I expect some kind of compensation credited to my credit…”

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Chicago Luxury Minibus City Tour and Architecture River Cruise - Cloud Gate offers a quick Millennium Park stop
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Chicago Luxury Minibus City Tour and Architecture River Cruise

8.Chicago Luxury Minibus City Tour and Architecture River Cruise

★★★★★★★★★★4.5 · 8 reviews · from $49

Spend about three and a half hours seeing Chicago from two useful angles: a guided downtown minibus ride and a 90-minute Chicago River architecture cruise. Joseph has led the bus tour, while the boat guide explains the city’s famous buildings. Expect short walks, photo stops, bottled water, and free Starbucks coffee onboard.

“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!”

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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour - Secret passages make the history feel real
3-Hour Experiences, Chicago Gangster Tours, Private, Tour Reviews, Tours, VIP

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

9.3-Hour Private Speakeasy Cocktail VIP Tour

★★★★★★★★★★5.0 · 7 reviews · 3 hours

Spend three hours with a private guide such as Alan or Kai, visiting three or four working Chicago speakeasies by luxury vehicle. Hear Prohibition and gangster stories, enter through secret passages, and buy period-style cocktails at each stop. Hotel pickup and drop-off within Chicago are included.

“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.”

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Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle - What your three-hour outing really includes
Chicago Architecture Tours, Private, Tour Reviews, Tours, VIP

Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle

10.Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle

★★★★★★★★★★3.5 · 7 reviews

Ride from your Chicago hotel to Oak Park in a private luxury vehicle and see up to 25 Frank Lloyd Wright buildings. The driver provides transportation only, not guiding or narration. You may stop at selected homes for photos, but interior tickets and the Frank Lloyd Wright Home and Studio tour cost extra.

“Your was about 1.5 hours and only involved pointing out the FLW houses. No knowledge of architecture or history.”

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O'Hare Airport Transfer to Chicago by Luxury Sedan - Inside Meet - The ride from O’Hare to your Chicago address
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O’Hare Airport Transfer to Chicago by Luxury Sedan – Inside Meet

11.O’Hare Airport Transfer to Chicago by Luxury Sedan – Inside Meet

★★★★★★★★★★5.0 · 6 reviews · 30 minutes to 1 hour (approx.)

Meet your Echo Limousine driver inside O’Hare’s baggage claim, get help with your luggage, and ride privately to a downtown Chicago address within five miles of the center. Drivers such as Rosa, Ogi, and Michelle have handled delayed flights and long customs waits with steady communication.

“two trips were on time, clean, and efficient. The drivers were polite and helpful. It was an easy way to relax and not worry to get between locations during long travel.”

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Chicago Luxury Flying Dress Photoshoot - Starting at The Chicago Theatre
Photography Sessions, Tour Reviews, VIP

Chicago Luxury Flying Dress Photoshoot

12.Chicago Luxury Flying Dress Photoshoot

★★★★★★★★★★5.0 · 5 reviews · 1h 30m · from $250

Meet photographer Elena Badea at The Chicago Theatre for a private Chicago photoshoot in a red or green transformer gown. You will walk to the Riverwalk, learn flattering poses, and receive an online gallery of edited photos within two to three days.

“I am pleased to highly recommend Elena Badea, the photographer who took these remarkable photos during our visit to Chicago. If you are in Chicago and need a photographer for any event, I strongly recommend her services. As a small business owner, she provides outstanding work. I had a wonderful time exploring the city and taking photos in this elegant, flowing dress. We attracted considerable attention, with people stopping to ask questions and show interest. I even noticed others taking pictures while Elena worked. My pictures turned out amazing and a few of my friends thought they were vogue quality. https://elenabadea.com/?fbclid=PAY2xjawJaQlJleHRuA2FlbQIxMQABpuUXxI1Sn68RXPpRAPjEEK_zDMYX...”

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Chicago 4-Hour Sightseeing Transfer by Luxury Private Sedan - What the driver does, and what the driver does not do
Chicago Private Car Transfers, Private, Private Drivers, Tour Reviews, VIP

Chicago 4-Hour Sightseeing Transfer by Luxury Private Sedan

13.Chicago 4-Hour Sightseeing Transfer by Luxury Private Sedan

★★★★★★★★★★4.5 · 5 reviews · 4 hours (approx.)

Set your own Chicago downtown route and ride in a private luxury sedan for four hours. A professional driver handles the driving, unlimited stops, and waiting time, but this is transportation rather than a narrated tour. Bottled water is included, and service runs 24 hours a day.

“This was not a true tour experience. Driver was very friendly, however, was not knowledgeable about any of the points of interest or history of the area.”

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Luxury Minibus Chicago City Tour - Palmer House and the brownie connection
Chicago Bus Tours, City Tours, Tour Reviews, Tours, VIP

Luxury Minibus Chicago City Tour

14.Luxury Minibus Chicago City Tour

★★★★★★★★★★5.0 · 4 reviews · 2 hours (approx.) · from $65

See Chicago’s best-known sights in about two hours by luxury minibus, with stops at Palmer House, Museum Campus, Buckingham Fountain, and the Rookery Building. Guides such as Avery and Logan add facts, humor, and local context while you ride past Soldier Field, the Field Museum, Millennium Park, and the Magnificent Mile.

“Filled with fun, obscure facts and the traditional tour details. Avery was personable, knowledgeable and downright funny at times.”

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Midway Airport Transfer to Chicago by Luxury SUV - Curbside - Finding the SUV at Midway’s lower level
Airport Transfers, Chicago Private Car Transfers, Midway Airport Transfers, Private Drivers, Tour Reviews, VIP

Midway Airport Transfer to Chicago by Luxury SUV – Curbside

15.Midway Airport Transfer to Chicago by Luxury SUV – Curbside

★★★★★★★★★★5.0 · 4 reviews · 30 minutes to 1 hour (approx.)

Meet your driver at Midway’s lower-level Door 2LL and ride privately to a downtown Chicago hotel in a luxury SUV. Echo Limousine tracks incoming flights, includes 60 minutes of wait time, and covers vehicles for up to six passengers and six bags. Drop-off must be within five miles of downtown.

“Our driver Sam arrived early to pick up our party of four. He carefully loaded our luggage into the SUV. He made sure we were all comfortable and proceeded with delivering us to Union Station without incident. Sam was a very courteous driver even showing us points of interest. Would definitely recommend Echo Limousine.”

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