Chicago · PRIVATE

15 Private Tours in Chicago to Build a Day Around

50 tours  ·  from $40

This is the shortlist you would send a friend: 15 private tours worth the money, each with its price, its traveller verdict and the one thing to know before you commit.

Private Art Institute of Chicago Skip-the-Line Guided Tour - The Impressionist Collection Takes Center Stage
Art Institute of Chicago Tickets, Guided, Private, Skip the Line, Tour Reviews, Tours

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 about 2.5 hours with an English-speaking guide such as Heath, Spiro, Samantha, or Mandy, touring the Art Institute’s major works and lesser-known rooms. Your ticket is included, the route can follow your interests, and the museum is wheelchair friendly.

“Heath was masterful! Weaving together hundreds of years of art history with culture, some politics, and a little self-reflection. From details about artists lives, to changes in popular culture, to specifics of paintings and everything in between and around them, Heath delivered a captivating and exciting trip through the Institute.”

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Chicago Private Custom City Tour with Hotel Pick Up - Lincoln Park and Chicago’s North Side
City Tours, Private, Tour Reviews, Tours

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.)

Explore Chicago by private vehicle with a guide and driver, stopping at Millennium Park, the Loop, Lincoln Park, Hyde Park, the University of Chicago, and Wrigley Field. Guides such as Todd, Mike, Matt, and Scott tailor the route to your interests, while downtown hotel pickup keeps the morning simple.

“The guide was super knowledgable and the driver was so smart about which route would get us safely to our destination. We did this tour as soon as arriving to Chicago and we are so glad we did! Thanks for helping to make our Chicago trip memorable!!!”

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Private Arrival Transfer from Chicago Airports (ORD) (MDW) - O’Hare versus Midway pickup
Midway Airport Transfers, O'Hare Airport Transfers, Private, Private Drivers, Tour Reviews

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 your Chicago hotel or Chicagoland address. Carmel provides a sedan for up to three or an SUV for larger groups, with 24-hour service, luggage help, and driver communication by phone or text.

“Outstanding....driver was very friendly. I will recommend to others whend traveling to Chicago. No issues and was present even I arrived.”

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Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max - The Impressionist collection is the main draw
Art Institute of Chicago Tickets, Private, Skip the Line, Tour Reviews, Tours

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 no more than seven other people. Expect major Impressionist works, iconic paintings, modern art, and historical context from guides such as Samantha, Heath, Joe, Mandy, and Spiro.

“Loved the Impressionists and the Miniature Rooms collections. Also enjoyed the Andy Warhol gallery and seeing Jackson Pollack’s work.”

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Private 45-Minute Chicago Skyline Helicopter Tour - Chicago sports from the air
Chicago Helicopter Tours, Helicopter Tours, Private, Tour Reviews, Tours

Private 45-Minute Chicago Skyline Helicopter Tour

5.Private 45-Minute Chicago Skyline Helicopter Tour

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

Fly privately from Schaumburg Regional Airport for about 45 minutes over Chicago’s skyline, Lake Michigan, Wrigley Field, Soldier Field, Millennium Park, Navy Pier, and the city’s famous towers. Pilots such as Steve, Matt, Tommy, Sara, and Chuck provide commentary and help with photos.

“Downtown Chicago is beautiful. Steve was very nice and help took photos of us. Would love to take another flight with him”

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Best of Chicago: Architecture & Highlights City Private Tour - Meeting the guide under the Chicago Theatre
Chicago Architecture Tours, Private, Tour Reviews, Tours

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 beneath the Chicago Theatre sign for a two-hour private walk through central Chicago. Explore the Pedway, Picasso Statue, Riverwalk, Tribune Tower, Magnificent Mile, and Millennium Park, with popcorn, chocolate, and a train pass included.

“Never would have known to "look up" at Macy's. We also went back to the Walnut Room for Mrs. Hering's chicken pot pie.”

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Private Departure Transfer to Chicago Airports (ORD)(MDW) - Meeting your chauffeur at the pickup address
Midway Airport Transfers, O'Hare Airport Transfers, Private, Private Drivers, Tour Reviews

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

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

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

Book a private one-way ride from a Chicago hotel or Chicagoland address to O’Hare or Midway. A chauffeur helps with luggage and takes you to your terminal. Sedans serve up to three people, while SUVs and limousines can carry up to six. Service runs around the clock.

“Before the agreed meeting time, the driver sent me a text message that he was waiting for us. Everything went very smoothly, the driver was elegant and friendly, the car was excellent.”

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Art Institute of Chicago Private Expert Guided Tour - Who should book this Art Institute tour?
Art Institute of Chicago Tickets, Guided, Private, Tour Reviews, Tours

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 with a private English-speaking guide at the Art Institute of Chicago. Ask for favorite works, focus on artists such as Van Gogh or Hopper, and see major pieces including Nighthawks, American Gothic, and Seurat’s La Grande Jatte.

“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 - Navy Pier from the water
Cruises & Boat Tours, Lake Michigan Boat Cruises, Private, Sailing, Tour Reviews

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.)

Book a private two-hour sail for up to six people from Navy Pier Marina. Your Coast Guard-licensed captain, possibly Mike, Ulysses, or Rich, adjusts the route to the wind and your interests, with skyline views, Bluetooth music, and time for drinks on deck.

“Lovely morning sail on Lake Michigan with the skillful, personable and knowledgeable Captain Ulysses!”

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Private Chicago Food Tour with Deep Dish and Beef Sandwich - Starting at the Hall Branch of the Chicago Public Library
Chicago Food Tours, Food, Food & Drink, Private, Tour Reviews, Tours

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

Walk Chicago’s Loop with a private English-speaking foodie guide, stopping for sausage deep dish, gourmet popcorn, a Chicago hot dog, Italian beef, a brownie, and a secret dish. Along the way, see Federal Plaza, Willis Tower, the Rookery, and the Palmer House lobby.

“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 ride itself: private, direct, and traffic dependent
Midway Airport Transfers, Private, Private Drivers, Tour Reviews

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

Arrange a private ride from Chicago Midway Airport to your downtown hotel, with airport pickup, an air-conditioned vehicle, a professional driver, and up to 60 minutes of included waiting time. Vehicle type depends on availability and group size, so confirm luggage and car expectations before booking.

“poor communication - driving skills were poor and almost rear ended another car-thank god for sensors on the car as that stopped us.”

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Chicago in a Day: Food and Architecture Private Walking Tour - Seeing the Riverwalk and Chicago’s towers
Chicago Architecture Tours, Chicago Food Tours, Chicago Walking Tours, Food, Food & Drink, Private, Tour Reviews, Tours, Walking Tours

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 with a Chicago guide such as Dave, Dash, Rich, David, or Laura, pairing landmark architecture with generous tastings of classic deep-dish pizza and hot dogs. Walk through the Loop, see the Riverwalk when weather allows, and keep your group private, with up to 12 people.

“Our tour guide was Chicago Dave . We had a wonderful time touring with him . We went to there different eating places all was excellent . History and architecture was really beautiful. Recommend this tour . Wear comfortable shoes a lot of walking . Thank you Chicago Dave (OG)”

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Chicago: ORD Airport Private Transfer to Chicago City|Hotels - What the one-hour ride really means
O'Hare Airport Transfers, Private, Private Drivers, Tour Reviews

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

You get a one-way private ride from Chicago O’Hare to your city hotel in an air-conditioned vehicle. An English-speaking Elife driver tracks your flight, contacts you by phone, WhatsApp, or text, helps with luggage, and waits up to 60 minutes after airport arrival.

“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 - Cloud Gate and the famous Chicago reflection
2-Hour Experiences, Chicago Walking Tours, Private, Tour Reviews, Tours, Walking Tours

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

Start at Pioneer Court and explore central Chicago with a private CTPA licensed guide for up to six people. Your two-hour walk can focus on architecture, art, food, shopping, or history. Guides including Leentje, Dave, and Mimi offer tours in English, French, or Dutch, with pickup available.

“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”

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Chicago: Private custom tour with a local guide - Why four to eight hours changes the experience
Guided, Private, Tour Reviews, Tours

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

Plan a private two to eight hour Chicago walk around the sights you care about most. Your guide can meet you at a central hotel, explain the city in English, French, Spanish, or Italian, and help arrange museum visits if requested ahead of time.

“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...”

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New in Private

★ 5.0Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking ClassFrom $594 reviews
★ 3.5Private Transfer from Chicago Airport (ORD)From $763 reviews
★ 5.0Private Sedan Transfer from Chicago Downtown to O`Hare airport9 reviews
★ 4.5Private Speakeasy Pub Crawl in Chicago with Local HistorianFrom $1015 reviews
★ 5.0Private SUV Transfer Between O’Hare airport & Downtown Madison WI4 reviews
★ 3.0Private Chicagoland One-Way Transfer by Mercedes Sprinter9 reviews
★ 3.5Private Vacation Photoshoot with Photographer in ChicagoFrom $1543 reviews
★ 5.0Private Holiday City Tour3 reviews
★ 5.0Welcome to Chicago: Private Half-Day Tour with 360 Observation DeckFrom $2403 reviews
★ 4.5Private Frida and Friends Tour in Pilsen6 reviews
★ 4.5Private Downtown Chicago TV and Movie Sites Guided Walking TourFrom $1323 reviews
★ 5.0Private Chicago Guided Tour with Hotel PickupFrom $8445 reviews
★ 5.0Private Chicago Architecture TourFrom $5395 reviews
★ 4.5Private Al Capone Gangster Tour in ChicagoFrom $5397 reviews
★ 3.5Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle7 reviews

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