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10 Best Chicago Private Tours to Book Right Now
Have you been wondering about Chicago private tours? You’ve come to the right place!
Chicago is a city with so much to offer and exploration of the Windy City through private tours is an incredible way to experience its unique and vibrant culture.
I lived in Chicago with my family for over 16 years and had the chance to take and give private tours showing off what makes the town so special. Of all the places we’ve traveled as a digital nomad family, Chicago is still one of my favorite cities.
I know all of the top spots for any great Chicago private tour: from Buckingham Fountain in Grant Park all the way up to the John Hancock Observatory, you’ll get to see many of Chicago’s must-see attractions on these curated tours.
Private tours offer a chance to hear the stories behind some of Chicago’s iconic architecture or get a taste of local cuisine at a restaurant off the beaten path.
There are plenty of great services providing private tours in Chicago, but every tour on this list is one I’d happily take myself (if I haven’t already) and/or recommend to friends and family visiting the Windy City. So let’s jump in! 💃
My Top 3 Picks: Chicago Private Tours
⭐️⭐️⭐️⭐️⭐️
Chicago Private Driver Tour
✅ Hotel Pickup
✅ Customizable Itinerary
✅ Knowledgeable Driver/Guide
45-Min Chicago Skyline Helicopter Tour
✅ See Chicago from above
✅ Noise Canceling headphones
✅ Free parking!
Lake Michigan Sailing Charter & Sightseeing
✅ Coast Guard certified captain
✅ BYOB & snacks
✅ Groups up to 6 welcome
Best 10 Chicago Private Tours
Booking a guided tour of Chicago just for your group is the perfect way to have an exclusive luxury tour Chicago experience while making the most of your time in the Windy City!
First, you’ll be picked up directly from your hotel in a clean and comfortable Chicago private car, so you can start your sightseeing adventure right away. And there no need to book separate Chicago history tours!
Your guide will fill you in on all the history and stories of Chicago as you drive around, making stops at highlights like Lincoln Park Conservatory, Millennium Park, Museum Campus, and other notable attractions.
See more of the city in a short amount of time without having to worry about navigating yourself or being stuck with long waits between locations. And if you want to see something that isn’t part of the tour, just tell your guide!
We had a foreign exchange student & decided to do the private tour in hopes that we might see a few different things & give her an idea of the city. It’s one of the best tours I’ve ever been on!
jennifer w (read more Reviews)
🔑 Key Essentials
☑️ Professional local guide/driver
☑️ Private transportation
☑️ Pick up at your Downtown Hotel
☑️ Stroller/wheelchair accessible
☑️ All ages welcome
☑️ Infant seats available
2. 45-Minute Chicago Skyline Helicopter Tour
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 45 Minutes | ✅ Book Now!
Soar high above the Windy City on a private 45-minute Chicago Skyline Helicopter Tour. Enjoy sweeping views of Chicago, including Navy Pier, Wrigley Field, Millennium Park, John Hancock Center, and Willis Tower.
This is the perfect way to celebrate any special occasion with someone special – this tour can accommodate up to three people comfortably!
Plus, you get the use of noise-canceling headsets so you can hear your pilot clearly as they take you on an unforgettable journey through the skies of Chicago. And you’ll get complimentary parking!
Whether you’re looking for a unique date night experience or just something to do with friends and family, this helicopter tour promises breathtaking views and an unforgettable adventure!
Flying over Wrigley Field – Where many family memories were made in the stadium and now over, Go Cubs!
Katrina f (read more Reviews)
🔑 Key Essentials
☑️ All Fees and Taxes included
☑️ Live commentary on board
☑️ Noise canceling headsets
☑️ Free Parking
☑️ Free photos of and in front of the helicopter!
☑️ Wheelchair/stroller accessible
☑️ Individual passengers must weigh less than 260 lbs
3. Lake Michigan Sailing Charter & Sightseeing Tour
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2 hours | ✅ Book Now!
Experience the wind in your hair and the sun on your face as you explore Lake Michigan on a private sailboat. You and up to five other invited guests will have exclusive use of the boat, complete with captain and crew.
With BYOB allowed, bring along your favorite beverages (just no glass containers) to enjoy while taking in the sights of Chicago’s striking skyline. This is one of my favorite ways to spend an afternoon in Chicago!
Your captain can provide narration about different landmarks along the way, but if you’d like to customize the itinerary to suit your group’s interests, just let him know.
Plus, if anyone wants to take a turn at the helm, they can! Don’t forget a Bluetooth-enabled device so that you can play your tunes while out on the lake. There’s truly nothing quite like sailing away and feeling completely free! ⛵️
The sail boat was beautiful and very clean…We loved the views of the city from the lake. It was my favorite outing of our trip to Chicago. Our teen kids had a great time too.
leslie m (read more Reviews)
🔑 Key Essentials
☑️ Professional US Coast Guard licensed captain
☑️ Use of Bluetooth speakers
☑️ All applicable taxes
☑️ All ages welcome
☑️ Bring seasickness medicines if needed
👉 Get Dramamine for everyone! There’s even a chewable version available for kids.
4. History, Culture, and Architecture Walking Tour
⭐️ RATING: 4.8/5 Stars | ⏳ TOUR LENGTH: 2.5 hours | ✅ Book Now!
From iconic architecture to tasty treats, there are plenty of unique experiences that will make your visit to The Windy City unforgettable. This private guided tour can help you explore the Loop and get around like a local.
You’ll have the opportunity to see some of the greatest hits of Chicago, such as incredible old and new buildings, stunning river views, and much more. You’ll also enjoy some classic snacks like Chicago-style popcorn and homemade chocolate.
You may also want to make time for visiting some of Chicago’s beautiful lakefront parks or museums so that you can feel the energy and buzz of this magnificent city.
No matter your interests, booking a private tour is a great way for you to experience all that Chicago has to offer. With an experienced guide leading the way, you’re sure to have an experience full of memories that will last a lifetime.
It was one of the best tours I have been on. Dave…took us places I never knew existed in Chicago and he inspired us about Chicago and how very unique and fun the city is.
nicole (read more Reviews)
🔑 Key Essentials
☑️ English-speaking guide
☑️ Popcorn tasting
☑️ Chocolate tasting
☑️ Eco-certified, carbon-neutral tour operator
☑️ All ages welcome
☑️ Tour is available in groups or private, so be sure to choose the private option when booking!
5. Private Chicago Highlights Driving Tour
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 3 hours | ✅ Book Now!
Take this private tour of Chicago and discover the beauty and history of some of the city’s most iconic monuments.
Tour the vibrant neighborhoods like The Loop, River North, Magnificent Mile (Michigan Avenue), Streeterville, Gold Coast, and more with your own private driver-guide and vehicle. You can even go past the Chicago Art Institute!
Get up close to towering skyscrapers (some designed by Louis Sullivan!) in awe, explore beautiful architecture, and immerse yourself in the vibrancy of the city.
Plus with round-trip hotel transport included as well as bottled water, you don’t have to worry about transportation or hydration! Experience Chicago’s top sights with an expert local guide who provides you with personalized service.
The tour was wonderful and our driver, Juan, was terrific! Thanks for a great experience!
jamie l (read more Reviews)
🔑 Key Essentials
☑️ Downtown Chicago hotel/port pickup and drop-off
☑️ PrivateDriver/Guide
☑️ 3-12 participants
☑️ Stroller accessible
☑️ Infant seats available
6. Customized Private Walking Tour in Chicago
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2 hours | ✅ Book Now!
One of my favorite ways to experience Chicago is through a customized private walking tour. With this best tour in Chicago by foot, you get to immerse yourself in the Windy City and its culture like never before!
With your knowledgeable guide, create an itinerary that meets all your individual interests, whether it’s history, architecture, street art, or Chicago’s food scene. And get recommendations for where to explore once the tour ends!
Art, food, shopping, and architecture fans can enjoy Chicago sightseeing tours tailored just for them! But no matter which type of tour you choose, every tour is different and tailored just for private groups of up to 6 people.
With a knowledgeable, private guide at hand, your day will be filled with amazing adventures that will give you memories that last a lifetime!
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.
kaaren a (read more Reviews)
🔑 Key Essentials
☑️ CTPA Licensed Guide
☑️ Hotel pickup is available or meet at a location of your choice
☑️ Tours are available in English, French, and Dutch
☑️ Wheelchair and stroller accessible
☑️ All ages welcome
7. Private Walking Food Tour With Secret Foods
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 3 hours | ✅ Book Now!
Your private walking food tour of Chicago is guaranteed to be the perfect way to explore the city’s most delicious eats! Delight in deep-dish pizza before your guide shows you sweet and savory treats that many visitors overlook.
As you go, you’ll get to learn about the history, architecture, and culture of this vibrant city. You’ll also enjoy enough treats and samples for a generous lunch along the way.
Wander through downtown Chicago with an expert guide who knows all the hidden gems. Your private tour gives you access to some of Chicago’s greatest culinary secrets without any crowds or long lineups.
For an unforgettable experience in one of America’s best cities for foodies, book this private walking foodie tour today! And be sure to show up hungry!
Sue…showed us great sites, pointing out interesting places that can be easily missed. Fabulous food! Every food stop was a winner. Enough food for lunch & supper.
tripadvisor reviewer (read more Reviews)
🔑 Key Essentials
☑️ Deep Dish Pizza with Sausage
☑️ Gourmet Popcorn
☑️ Chicago-style Hot Dog
☑️ Italian Beef Sandwich
☑️ Brownie
☑️ A delicious Secret Dish
🤩 Check Rates and Availability! 🤩
8. All-Inclusive Chicago Foodie Tour: Windy City Favs
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 4 hours | ✅ Book Now!
Treat your taste buds to all the best Chicago has to offer with a private foodie tour of the city. This excursion Chicago offers all my local favorites, so you’re sure to enjoy it!
From deep-dish pizza and Italian beef sandwiches to hot dogs, and donuts, you’ll have a hard time deciding which tastes better. All while taking in some of the city’s most iconic sites like the Wrigley Building and Magnificent Mile.
Get an insider look at Millennium Park and The Rookery Building, among other landmarks. These local spots provide an authentic glimpse into the culture and history of this great city.
Your private guide will not only show you around the historic sites but also share stories and facts about each location that make it unique. Don’t miss your chance to explore Chicago’s top sightseeing spots while feasting on its famous eats!
Great hot dog!! A lot of insider info from the guide. Went to places I would have missed on my own! Learned a lot of history. Great communication leading up to the event.
terri h (read more Reviews)
🔑 Key Essentials
☑️ An Uber ride
☑️ English speaking tour guide
☑️ All tastes and fees
☑️ Bottled water
☑️ 1 Portillos hotdog
☑️ 1 small Garrett’s popcorn
☑️ 1 6-inch Al’s Italian Beef sandwich
☑️ 1 slice of deep-dish pizza
☑️ 1 Do-rite Donut
☑️ Stroller accessible
☑️ All ages welcome
🤩 Check Rates and Availability! 🤩
9. Evening Sail in Chicago w/Navy Pier Fireworks
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2 hours | ✅ Book Now!
One of my favorite ways to spend an evening in Chicago is sailing while watching the Navy Pier Fireworks!
Treat yourself to an unforgettable experience on a private sailboat cruise that will take you along the beautiful lakefront of the iconic city. Enjoy a breathtaking view of the skyline as you watch the incredible fireworks from Navy Pier.
You and up to five others will have two hours to explore, customize your trip and make memories along the way.
Your U.S. Coast Guard licensed captain will be sure to provide a safe and intimate voyage, with your choice of music, route, and guest list so you can create a personalized evening worth remembering!
This was a great experience. Our captain was great and the view of the fireworks was breathtaking. Such an incredible experience. I defended recommend!
freeman r (read more Reviews)
🔑 Key Essentials
☑️ Professional US Coast Guard licensed captain
☑️ Use of Bluetooth speakers
☑️ All applicable taxes
☑️ All ages welcome
☑️ Bring Dramamine if anyone in your party is prone to seasickness
👉 Get Dramamine for everyone! There’s even a chewable version available for kids.
🤩 Check Rates and Availability! 🤩
10. Chicago Lakefront Electric Bike Tour
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 1-2 hours | ✅ Book Now!
Make your Chicago experience one to remember with a private electric bike tour. Explore the city like never before, zipping along Lake Michigan and viewing the Chicago skyline from picture-perfect spots.
On your journey, you’ll see the iconic Buckingham Fountain, Field Museum, Adler Planetarium, and other landmarks.
Get up close and personal with the architecture, landmarks, and history of Chicago on this private electric bike tour. Your personal guide will provide an immersive experience as you ride along effortlessly on an e-bike.
Perfect for those 12+ who can ride their own full-size bike, this tour offers an unforgettable way to explore Chicago’s waterfront sights in record time.
Getting a close view of all attractions in Chicago, while having fun on a electric bike. Our tour guide was great and he even stopped to take photos!
orece c (read more Reviews)
🔑 Key Essentials
☑️ Use of bicycle and helmet
☑️ Bottled water & snacks provided
☑️ Participants 12+ only
☑️ Infant bike seats and tagalongs are not available
🤩 Check Rates and Availability! 🤩
Final Thoughts: Private Guided Tours Chicago
Chicago private tours are the best way to make sure you see everything in the Windy City that you want to.
With so many unique districts and attractions, personal tours allow you to tailor your experience to what appeals most to you.
🤩 The Chicago Private Driver Tour is the best choice for an exclusive, luxurious experience with maximum flexibility! 🤩
With an experienced guide, it’s easy to make sure you get a great view of every stop on your list. From stunning views of Lake Michigan to the endless nightlife of Wicker Park, there’s something for everyone in Chicago.
No matter how much time you have in Chicago, there’s no better way to ensure you get the absolute most out of the city than with a private best Chicago tour.
So don’t wait any longer – check out one of these amazing options and book one of the private tours Chicago offers today!
Each of these experienced Chicago tour guides can show you all the sights that this incredible city has to offer and ensure that your experience is as amazing as possible.
🤩 Looking for other fun things to do in Chicago? While there aren’t any private options, the Chicago Architecture Tour River Cruise is one of my favorite group tours in Chicago! 🤩
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