Chicago · CHICAGO PRIVATE TOURS

15 Chicago Private Tours to Plan a Day Around

52 tours  ·  from $40 a head

One free afternoon and too many choices. These 15 chicago private tours justify the slot, priced and timed so you can choose in minutes and get back out to the lakefront.

Private Art Institute of Chicago Skip-the-Line Guided Tour - What makes the storytelling useful
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Private Art Institute of Chicago Skip-the-Line Guided Tour

1.Private Art Institute of Chicago Skip-the-Line Guided Tour

★★★★★★★★★★5.0 · 275 reviews · 2 hours 30 minutes (approx.) · from $85Our pick

Spend 2.5 hours at the Art Institute of Chicago with an English-speaking guide and admission included. The route can be adjusted to your interests, with time for major works, art movements and less familiar corners. Guides named in recent feedback include Heath, Spiro, Samantha and Mandy, but your guide is not guaranteed.

“Very informative guide. Passionate about Art and it came through. Offered flexibility but we went with his program and hit all the highlights. I will take this tour agin if I ever return to Chicago. Excellent job Arnold! Thanks.”

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Chicago Private Custom City Tour with Hotel Pick Up - Lincoln Park and the North Side
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Chicago Private Custom City Tour with Hotel Pick Up

2.Chicago Private Custom City Tour with Hotel Pick Up

★★★★★★★★★★5.0 · 201 reviews · 3 to 4 hours (approx.)

In three to four hours, a private guide and driver take your group of up to five from your downtown hotel to Millennium Park, the Loop, Lincoln Park, the University of Chicago and Wrigley Field. Guides such as Todd, Mike and Scott have led tours with city stories and flexible stops. Expect a broad overview, not a long visit at every landmark.

“I have seen much of downtown Chicago before. We had a foreign exchange student and decided to do the private tour in hopes that we might see a few different things and also give her an idea of the city. It was one of the best tours I have ever been on! I can't remember the names of our guide and driver, but they were fun, friendly, knowledgeable, and willing to do what was needed...even let my husband ride up front after he was feeling a bit car sick. Anyway, I would highly recommend spending the extra money for the private tour. We saw so many things that we wouldn't…”

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Private Arrival Transfer from Chicago Airports (ORD) (MDW) - Sedan or SUV: match the car to your luggage
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Private Arrival Transfer from Chicago Airports (ORD) (MDW)

3.Private Arrival Transfer from Chicago Airports (ORD) (MDW)

★★★★★★★★★★3.5 · 196 reviews · 1 hour (approx.)

Book a private, one-way ride from O’Hare or Midway to a downtown Chicago or wider Chicagoland address. A chauffeur meets you at the airport and takes your group by sedan or SUV, with service available around the clock. The quoted transfer is about an hour, but traffic sets the pace.

“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.”

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Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max - What the guide adds beyond the wall labels
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Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

4.Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

★★★★★★★★★★5.0 · 157 reviews · 2 hours 30 minutes (approx.) · from $85

Spend 2.5 hours inside the Art Institute of Chicago with a guide and a semi-private group. You’ll cover major works, including Impressionist art, while hearing about artists, styles, and the museum’s collection. Guides have included Samantha, Heath, Joe, Mandy, and Spiro, though your guide may vary. Admission is included; expect plenty of walking.

“Joe was a great guide! He was very knowledgeable, I learned a lot and got to see some highlights of the museum!”

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Private 45-Minute Chicago Skyline Helicopter Tour - Millennium Park and the lakefront from above
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Private 45-Minute Chicago Skyline Helicopter Tour

5.Private 45-Minute Chicago Skyline Helicopter Tour

★★★★★★★★★★5.0 · 126 reviews · 45 minutes (approx.)

Take a private helicopter flight from Schaumburg Regional Airport toward Chicago’s skyline, with views of Willis Tower, the John Hancock Center, Millennium Park, and both Cubs and Bulls territory. Your pilot provides commentary in English, and in-flight headsets and parking are included. Pilots named on past flights include Matt, Steve, Steven, Tommy, Chuck, and Sara.

“Everything! The experience of this helicopter ride in general will always be memorable. Being able to see the changing of the leaves from above. Matt's knowledge of Chicago, his kindness & patience was truly appreciated.”

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Best of Chicago: Architecture & Highlights City Private Tour - Follow the city beneath the streets
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Best of Chicago: Architecture & Highlights City Private Tour

6.Best of Chicago: Architecture & Highlights City Private Tour

★★★★★★★★★★5.0 · 94 reviews

Meet your English-speaking guide outside the Chicago Theatre for a private walk through downtown. You’ll see the Picasso, the Chicago Pedway, landmark towers and Millennium Park, with a train pass and popcorn and chocolate tastings included. Guides have included Dash, Rich, Dave and David, though your guide may vary. The Riverwalk stop is weather-dependent and omitted in winter.

“We learned so much about the architectural history of Chicago on this tour. Rich was a great guide! Also enjoyed the Garrett popcorn and the Franco chocolate samplings!”

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Private Departure Transfer to Chicago Airports (ORD)(MDW) - How the pickup and ride work
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Private Departure Transfer to Chicago Airports (ORD)(MDW)

7.Private Departure Transfer to Chicago Airports (ORD)(MDW)

★★★★★★★★★★4.0 · 91 reviews · 1 hour (approx.)

Arrange a private ride from your Chicago hotel or another Chicagoland address to O’Hare or Midway. A chauffeur collects your group, helps with bags, and drives you to your departure terminal in a sedan for up to three people or a larger vehicle for a bigger party. Service runs 24 hours a day, but confirm your vehicle, pickup details, and total price in advance.

“Great driver from downtown Chicago hotel to airport! Very nice and on time. Helpful with luggage! Highly recommend!”

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Art Institute of Chicago Private Expert Guided Tour - What a good guide adds
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Art Institute of Chicago Private Expert Guided Tour

8.Art Institute of Chicago Private Expert Guided Tour

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.) · from $215

Spend about two hours at the Art Institute of Chicago with a private English-speaking guide and skip-the-line entry. You can shape the route around your interests, ask questions, and see major works such as Nighthawks, American Gothic, and A Sunday on La Grande Jatte. Guides have included Joe, Colleen, Marlin, and Heath. Morning tours include early admission.

“Joe was an amazing guide. Informative and very interesting! Explained the history of the artist as well as the painting.”

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Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago - Chicago’s skyline, framed by Lake Michigan
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Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

9.Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

★★★★★★★★★★5.0 · 70 reviews · 2 hours (approx.)

Sail Lake Michigan with your own group of up to six, departing from Navy Pier Marina for a two-hour private charter. Your captain adjusts the route to the wind and your interests, with possible views of the skyline, Adler Planetarium, Soldier Field, and Buckingham Fountain. Bring your own drinks and music, and ask captains such as Mike or Ulysses about sailing and Chicago.

“A great time out on the lake. Our captain was very capable and informative. I would recommend for just a fun experience or for a special occasion.”

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Private Chicago Food Tour with Deep Dish and Beef Sandwich - Starting at the library and entering the Loop
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Private Chicago Food Tour with Deep Dish and Beef Sandwich

10.Private Chicago Food Tour with Deep Dish and Beef Sandwich

★★★★★★★★★★5.0 · 61 reviews · 3 hours (approx.) · from $224

Spend about three hours on a private Chicago walking tour with a local food guide, tasting deep-dish pizza, Italian beef, a Chicago-style hot dog, popcorn, a brownie and a surprise dish. The route links downtown landmarks, including the Rookery and Calder’s Flamingo, and ends near Millennium Park. No guide names are provided.

“Need to walk and be hungry. This was an awesome combination of history of Chicago food but all history.”

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Private Transfer Chicago Airport MDW to Chicago Downtown - The vehicle is assigned, not guaranteed by a photo
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Private Transfer Chicago Airport MDW to Chicago Downtown

11.Private Transfer Chicago Airport MDW to Chicago Downtown

★★★★★★★★★★3.5 · 54 reviews · 30 minutes to 1 hour (approx.) · from $50

Travel privately from Chicago Midway Airport to downtown in an air-conditioned vehicle with a professional driver. The ride takes about 30 minutes to an hour, depending on traffic. Vehicle type depends on availability and your group size, so confirm luggage capacity and pickup details before you fly.

“Great driver. My daughter forgot her earbuds and Cheng was so nice, he went back to hotel to return them. Highly recommend.”

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Chicago in a Day: Food and Architecture Private Walking Tour - The Chicago River and its changing skyline
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Chicago in a Day: Food and Architecture Private Walking Tour

12.Chicago in a Day: Food and Architecture Private Walking Tour

★★★★★★★★★★5.0 · 53 reviews · from $272

Spend about five hours exploring Chicago’s architecture and food with a private guide, with your group capped at 12. Start near the Chicago Theatre, pass landmarks such as the Wrigley Building and Chicago Water Tower, then sample local favorites including deep-dish pizza and hot dogs. Guides have included Dash, Chicago Dave, Rich, and Lara.

“Chi-Tall Dave is an amazing tour guide. He gave us insight on Chicago then and now. The food stops were delicious and architecture locations were beautiful. Worth it and can’t wait to come back and try all these stops with family and more friends.”

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Chicago: ORD Airport Private Transfer to Chicago City|Hotels - What the one-hour estimate means for your arrival
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Chicago: ORD Airport Private Transfer to Chicago City|Hotels

13.ORD Airport Private Transfer to Chicago City|Hotels

★★★★★★★★★★4.2 · 46 reviews · from $40Best value

An English-speaking Elife Ride driver collects you at ORD and takes you directly to your Chicago accommodation in a private, air-conditioned vehicle. Your driver tracks your flight and contacts you by phone, text, or WhatsApp to set a meeting point. The ride is listed at about one hour; no individual driver name is provided.

“Thank you for great service! The drive to my hotel was smooth! A great start for my first time in Chicago!”

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Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago - Pioneer Court sets the scene
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Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

14.Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

★★★★★★★★★★5.0 · 35 reviews

Set out from Pioneer Court with a private guide for a two-hour Chicago walk tailored to your interests. The route can focus on architecture, art, food, shopping, or city history, and may include Millennium Park’s Cloud Gate, Crown Fountain, and landmark sculptures. Guides have included Leentje, Dave, and Mimi. The $220 group price covers up to six people.

“Dave was very friendly, knowledgeable and easy going. He took us to sites we had walked by many times without knowing the history. Our 18 year old was fascinated by the tour as well.”

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Chicago: Private custom tour with a local guide - Make the guide part of the planning
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Chicago: Private custom tour with a local guide

15.Private custom tour with a local guide

★★★★★★★★★★4.4 · 28 reviews · 2 - 8 hours · from $129

Shape a private Chicago walking tour around the sights and areas you care about, with a local guide, hotel pickup in the city, and options for 2 to 8 hours. Guides speak English, French, Italian, or Spanish. Bart has been praised for explaining Chicago history in French, though guide assignments vary.

“Service sublime notre guide Bart nous a bien expliqué l’histoire de Chicago le tout dans un français parfait :) une visite à faire on aurait du prendre davantage de temps que 2h je recommande vivement cette visite en français de l’histoire de Chicago”

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Chicago, by the kind of day

Pick a deck, a dock or a table.