15 VIP Experiences in Chicago Worth an Afternoon

1.Field Museum of Natural History Ticket or VIP Tour

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

Spend a day at Chicago’s Field Museum, home to Sue the T. rex, Maximo the Titanosaur, the Lions of Tsavo, and more than 35 exhibitions. Choose general admission, a pass with one special exhibition, an All-Access Pass, or an early VIP dinosaur tour with a museum docent. The VIP tour takes place before opening and includes all-access admission.

“Cool experience. Loved Egypt and the dinosaurs. The building is cool too!”

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

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

Skydeck Chicago pairs after-hours access to Willis Tower’s 103rd-floor Skydeck with a three-course Giordano’s meal. Choose a seating time, salad, dessert, drinks, and up to six pizza toppings. You get 1.5 hours at your table, plus time to see the Chicago skyline and visit the glass Ledge without the regular daytime crowd.

“What an amazing experience. This was really special. We had the Skydeck to ourselves and the most incredible views of the city at night. The food was delicious. We didn't think it would be enough but we couldn't finish it.. we took as many photos as we wanted out on the Ledge with the city's lights as our backdrop. Really special evening with a very tasty Chicago Pizza Pie in the Sky. 👌”

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3.Chicago Gangsters and Ghosts Luxury Minibus Tour

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

Spend about two hours exploring Chicago’s Loop by bus with a guide and licensed driver. Hear stories tied to gangsters and ghosts, see landmarks including Holy Name Cathedral and Death Alley, and visit Frank Nitti’s vault at Harry Caray’s Italian Steakhouse. Guides have included Ty, Alan, Matthew, Kris, Avery and Karina.

“Alan was a great speaker, he gave us lots of stories and information. I would recommend this tour…..”

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

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

Travel from O’Hare to your Chicago address in a private SUV for up to six people. After landing, you’ll get a text with the driver’s details, collect your bags, then call or text to meet at the airport’s middle limousine lane. The ride takes about 30 minutes to an hour, depending on traffic.

“Driver on time and car very clean Polite and professional driver The drivers need to know that commercial cars DO NOT NEED car seats for kids, as per the Department of Chicago Police”

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

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

Arrange a one-way private transfer between Chicago’s Loop and O’Hare in a luxury SUV. The service runs around the clock, takes about 30 minutes to an hour depending on traffic, and includes a 10-minute wait. The stated $155 fare covers a vehicle for up to five, while the SUV is described as seating up to seven, so confirm the right capacity and price for your group before booking.

“Professional on time and nice car. What more can u ask for out of a car service that takes you to the airport”

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

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

Book a one-way private sedan for up to three people between Chicago’s Loop and O’Hare. The ride takes about 30 minutes to an hour, depending on traffic, and service runs day and night. Expect a professional driver, a clean, comfortable car, and 10 minutes of complimentary waiting time. Meet-and-greet service is not included.

“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.”

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

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

After landing at O’Hare, you’ll get a text with your driver’s details, then meet at the baggage-claim area assigned to your flight. A private luxury SUV takes your group of up to six to your Chicago address. Luggage help, parking, taxes, fees, gratuities, and bottled water are included.

“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.”

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8.Chicago Luxury Minibus City Tour and Architecture River Cruise

★★★★★★★★★★4.5 · 8 reviews · from $49

This small-group city tour pairs a guided downtown minibus ride with a 90-minute Chicago River architecture cruise. You’ll stop at Museum Campus and Cloud Gate, then pass landmarks from the Water Tower to Willis Tower. Joseph is one named minibus guide; boat guides vary. Bottled water and Starbucks coffee are included.

“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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9.3-Hour Private Speakeasy Cocktail VIP Tour

★★★★★★★★★★5.0 · 7 reviews · 3 hours

Spend three hours with a private guide visiting three or four working Chicago speakeasies, some preserved in their original condition. Enter by secret passages, hear stories of bootlegging and racketeering, and get cocktail recommendations inspired by the era. Alan and Kai have led the tour, though your guide may differ. Luxury transport and city-limit hotel pickup are included; drinks cost extra.

“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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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 pass 25 Frank Lloyd Wright buildings. You can request stops for photos, but the service provides transportation only, with no guide, narration, or admission tickets. The outing takes about three to eight hours, and extra time beyond three hours is billed in half-hour increments.

“I love Wright's architecture. Early Prarie Style and Craftsman. His life story as explained by our guide Jerry was very sordid. Multiple marriages and relationships while leaving wife and children alone with no financial support while he was earning large commissions on hiRead more”

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

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

Echo Limousine picks you up inside O’Hare’s baggage-claim area and drives your party of up to three to an address within five miles of downtown Chicago. Expect a driver-information text, help with luggage, and a private sedan ride of about 30 minutes to an hour. Drivers named on past trips include Ogi, Rosa, and Michelle.

“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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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. She guides your poses as you walk toward the Riverwalk, using the city’s architecture as a backdrop. The session lasts 90 minutes, with an online gallery emailed within two to three days.

“She was so sweet and we had a great time it was fun”

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

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

Set your own Chicago downtown route with a private sedan and professional driver for up to three people. You have four hours, unlimited stops and waiting time, and bottled water. Send your preferred attractions in advance, or ask for help planning. This is transportation, not a narrated tour, so bring your own guidebook or audio tour if you want context.

“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.”

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14.Luxury Minibus Chicago City Tour

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

In two hours, this English-language minibus tour links the Palmer House lobby, Museum Campus, Buckingham Fountain, the Rookery and major sights along the way. Guides Avery and Logan have led tours, though your guide may differ. Expect quick photo stops, city stories and a broad overview rather than long visits inside attractions.

“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!”

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

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

Echo Limousine provides a private, one-way SUV transfer from Midway to an address within five miles of downtown Chicago. You get curbside pickup, flight tracking, and 60 minutes of complimentary wait time. Your driver’s name and vehicle details arrive by text after landing. The ride usually takes 30 minutes to an hour, depending on traffic.

“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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