11 Best Private Chicago Tours To Take In 2024
Chicago is such an interesting city, from its historic architecture to its vibrant food scene. One of the best ways to experience the city is by taking one of the private Chicago tours.
By taking a private tour in Chicago, you’ll explore the city’s highlights while avoiding the crowds of a group tour. It is an incredible way to experience the city!
As someone who lives in the Midwest, I’ve visited Chicago many times and experienced a variety of the best things to do in the city. Based on this personal experience, I’ve created a list of the best private Chicago tours that will help you explore the city and see everything from iconic sites to hidden gems.
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Here is a quick guide to the best Private Chicago Tours:
Best Tour Overall – Chicago Private Custom City Tour
Best for Incredible Views – Private 45-Minute Chicago Skyline Helicopter Tour
Best for History & Architecture – Best of Chicago: Architecture & Highlights City
Best Private Chicago Tours
Below you will find a list of the best private tours in Chicago. These include a variety of tours from driving tours, walking tours, boat tours, and even helicopter tours. All of these private tours are highly rated and are a great way to experience the city.
1. Chicago Private Custom City Tour with Hotel Pick-Up
Taking this luxury private tour is easily one of the best ways to experience the highlights of Chicago. It’s perfect for those who are short on time or would like to see the main sites within a half-day.
The private tour starts with pick-up from your hotel. From there, your guide will show you the most iconic places in Chicago, including the Lincoln Park Conservatory, Millennium Park, Museum Campus, Wrigley Field, and more.
Along the way, you’ll learn about the fascinating stories and history of Chicago from your local guide.
Not only will you learn about Chicago and see its most famous landmarks, but you will also get to enjoy a relaxing ride around the city which is a great way to experience Chicago.
This private tour is also highly rated. It has an outstanding 4.9/5 stars with many reviewers mentioning how knowledgeable and friendly the tour guide is and how it was such a fun way to explore the city.
Why Choose the Chicago Private Custom City Tour?
- Roundtrip transportation from your hotel
- Luxury private tour with a local guide
- Visit Chicago’s most famous sites in a half-day
Book the Chicago Private Custom City Tour with Hotel Pick-Up
2. Best of Chicago: Architecture & Highlights City Private Tour
If you want to experience the best of downtown Chicago, this walking tour is a fantastic option! You will get to explore the main sites plus learn about the history and hidden gems of downtown.
You will meet your tour guide outside the historic Chicago Theatre which dates back to 1921. From there you will go on a walking tour through the heart of downtown, seeing places like the Picasso Statue, the Chicago Riverwalk, the Magnificent Mile, Millennium Park, and more.
During the tour, your guide will tell you more about the architecture, history, and interesting stories about the city.
The walking tour lasts for 2 hours and there are several different times to choose from which makes it easy to fit into your Chicago itinerary. It’s a perfect way to explore the city in a short time frame.
Why Choose the Best of Chicago: Architecture & Highlights Tour?
- Walking tour of downtown Chicago with a local guide
- See the most iconic places in the city
- Hear more about the history and stories of Chicago
- The tour is 2 hours which is perfect for those who are only in Chicago for a short time
Book the Best of Chicago: Architecture & Highlights City Private Tour
3. Private 45-Minute Chicago Skyline Helicopter Tour
This Chicago helicopter tour is the ultimate bucket list experience. On this 45-minute flight, you will get the absolute best views of the famous Chicago skyline. You’ll also fly over Chicago’s iconic landmarks including the Navy Pier, Millenium Park, and Wrigley Field.
Soaring around the city via a private helicopter tour is an amazing way to experience Chicago. It’s the perfect activity for a special occasion or a memorable date night. No doubt about it, taking a helicopter ride across the city is sure to be the highlight of your trip!
This helicopter tour is a private tour for up to 3 people. It includes noise-canceling headphones and commentary from the pilot while on board. You’ll also get photos in front of the helicopter before taking flight.
If you’re looking to expand your helicopter tour experiences beyond Chicago, check out these exciting Detroit helicopter tours for a unique way to see another iconic city from above!
One thing to note is that helicopter tours can book up fast, so make sure to book this in advance!
Why Choose the Private Chicago Skyline Helicopter Tour?
- 45-minute private helicopter tour
- Once in a lifetime experience
- The best views of the Chicago skyline
- Option to take photos in front of the helicopter
Book the Private Chicago Skyline Helicopter Tour Here
4. Chicago River Architecture and History-Private Boat Tour
The Chicago River is an iconic part of Chicago as it runs directly through the downtown area. So, one of the most unique ways to experience Chicago is by boat. On this private Chicago River boat tour, you will get to experience the city’s architecture while sailing down the famous river.
The tour starts with a short walk so that you can see some of the famous sites like the Chicago Theater. Then, you will make your way to your private boat where you will enjoy a 2.5-hour private boat tour along the Chicago River.
Along the way, you will pass by some of Chicago’s most interesting buildings including the Willis Tower, Merchandise Mart, Macy’s on State Street, the Wrigley Building, and more. You’ll also have a private guide who will explain more about the history of Chicago and how that history has shaped the city’s identity today.
If you like history, this is definitely the tour for you! However, even for those who aren’t history buffs, this is still an incredible way to learn about the city and enjoy a fun boat ride through the downtown area.
Why Choose the Chicago River Architecture & History Boat Tour?
- Short walking tour to see gems like the Chicago Theater
- Private, comfortable boat tour down the Chicago River
- Unique views of the city from the river
- Learn more about Chicago’s history from an expert guide
Book the Private Chicago River Boat Tour Here
5. Chicago: Private Custom Tour with a Local Guide
Chicago is such a big city that it can be overwhelming to decide what to see, especially if you are only visiting for a short time. This customizable private tour is the perfect option for those who want to be able to see things that interest them the most.
The best part about this tour is that you’ll benefit from having an expert local guide who can help you narrow down and customize what you want to see during your tour. This means that you can opt to see the most famous sites of the city or explore some of Chicago’s hidden gems. Either way, you’ll benefit from having a knowledgeable, local tour guide who really knows the city.
There is also the option to book a 2, 3, 4, 6, or 8-hour tour which allows you to have lots of flexibility with your itinerary.
Why Choose the Private Custom Tour of Chicago?
- Customizable tour allowing you to experience the main sites or hidden gems
- Flexibility to choose between 2, 3, 4, 6, or an 8-hour tour
- Local guide with expert knowledge of the city
Book the Private Custom Tour of Chicago Here
6. Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
If you are visiting Chicago during the warmer months, then taking this sailing tour on Lake Michigan is an absolute must-do activity.
Not only will you get to enjoy a day out on one of the Great Lakes, but you will also get to enjoy a private sailboat which is a super unique experience!
Taking a sailboat tour is a fun way to experience the city as you will get to enjoy the skyline views while you sail around the lake. Your private sailboat comfortably fits 6 people, plus a captain and crew so that you can sit back, relax, and enjoy.
As someone who has visited Chicago on several occasions, I definitely recommend spending time on Lake Michigan during the summer. This sailing experience is the perfect way to enjoy Chicago away from the crowds while also experiencing the natural beauty of Lake Michigan.
Why Choose a Private Sailing Tour of Chicago?
- Private sailboat for 6 people
- Includes captain and crew
- Flexible itinerary based on your interests
- Incredible views of Lake Michigan and the Chicago skyline
Book the Private Sailing Tour of Chicago Here
7. Private Chicago Architecture Tour
For those who are interested in architecture, this is the perfect tour to take of Chicago. On this private tour, you will get to see the best architectural highlights of the city including Willis Tower (formerly known as the Sears Tower), the John Hancock Building, homes designed by Frank Lloyd Wright, the Chicago Bean Statue, and more.
One of the best parts of this tour is that you won’t just see these famous Chicago landmarks, but you will get to go inside and explore some of these historic buildings.
You will also get a chance to take a photo in front of the famous Bean Statue at the end of the tour!
The tour is a 3-hour private tour with a guide who is an expert in the city’s history and architecture. The tour can also be customized based on your interests.
Why Choose the Private Chicago Architecture Tour?
- A private 3-hour tour that can be customized
- Experience the interiors of some of Chicago’s most famous buildings
- See the architectural highlights of the city including historic brownstones, Frank Lloyd Wright homes, the Willis Tower, and more.
Book the Private Chicago Architecture Tour Here
8. Private Chicago Highlights Driving Tour
This is the perfect tour to see the highlights of Chicago in just one day. Since this is a driving tour, you will be able to cover more areas vs taking a walking tour.
During this tour, you will get to explore some of the city’s most vibrant areas, including the Loop, the Gold Coast, the Magnificent Mile, and more.
Plus, you will get to see the top landmarks like Millennium Park and Navy Pier. It’s an easy and fun way to explore the windy city!
This is a good option for larger families or a group of friends, as this private tour can accommodate up to 7 people. The tour also includes roundtrip transportation from your Chicago hotel.
Why Choose the Chicago Highlights Driving Tour?
- Driving allows you to cover more areas and iconic sites
- Round-trip transportation from your hotel
- The tour can accommodate larger families
- Knowledgable, local guide
Book the Private Chicago Highlights Driving Tour Here
9. Chicago in a Day: Food and Architecture Private Walking Tour
This private tour is a great way to experience the culture of Chicago as it combines the famous landmarks with a food tour.
During this tour, you will explore the heart of downtown Chicago and see sites like the Chicago River and Millenium Park.
Then, you’ll head over to the Central Loop area to try samples of the best foods in the city. Make sure you come hungry for this tour because Chicago is known for its incredible food, from its deep-dish pizza to its famous Chicago-style hot dogs.
During the food tour, your guide will tell you the interesting stories of the everyday chefs who contributed to Chicago’s diverse food scene. It’s a great way to learn more about Chicago’s culture while also trying some tasty food!
Why Choose the Chicago in a Day: Food and Architecture Tour?
- Private walking tour of downtown Chicago with a local guide
- Visit highlights like the Chicago River and Millenium Park
- Try samples of iconic Chicago foods like deep-dish pizza
Book the Chicago in a Day: Food and Architecture Private Tour
10. Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
This private walking tour is 100% customizable which allows you to focus on what you are most interested in. Choose to learn about Chicago’s history, visit the famous sites, see the street art, or explore Chicago’s food scene.
Each tour is tailored to your interests and the local guides are experts on Chicago’s art scene, food, shopping, and architecture.
I’d highly recommend doing this tour at the beginning of your trip as the guide will also give you some great recommendations after the tour of more places to visit, eat, or shop in the city.
Why Choose Your Way or the Highway: Private Walking Tour?
- 2-hour private walking tour with an experienced local guide
- Customize the tour based on your interests
- Tours can focus on art, architecture, shopping, food, or a combination of these
Book the Your Way or the Highway: Private Walking Tour
11. Chicago Private Sunset Sail on Lake Michigan
This private sunset tour is the perfect way to celebrate a special occasion or enjoy a romantic date night while in Chicago. The tour includes a private sailboat ride on Lake Michigan during sunset. Seeing the sunset along Chicago’s skyline is an incredible experience, and easily one of the best ways to enjoy a night in the city.
The sunset sailboat cruise comfortably fits 6 people, and you will also have a coastguard-certified captain. You can also bring your own food and drinks on board so that you can enjoy the amazing views while enjoying your favorite drink.
The sailboat charter is also customizable so that you can decide on your own route or let the captain sail you around to see some of the best views from the water.
Why Choose the Chicago Private Sunset Sail on Lake Michigan?
- Experience the beauty of Lake Michigan on a sailboat
- See the stunning sunset over the Chicago skyline
- Private sailboat with a captain so that you can relax and enjoy the views
Book the Chicago Private Sunset Sail on Lake Michigan
Conclusion
Taking one of these private Chicago tours is an amazing way to experience the largest city in the Midwest. From iconic skyline views to historic architecture, the city of Chicago is a vibrant and fun place to visit, and there is so much to explore here.
While there are many great tours, if you are looking for the best private tour, I highly recommend checking out the Chicago Private Custom City Tour. This luxurious private tour will take you to the highlights of the city, is customizable based on your interests, and even includes hotel pickup. It is the perfect way to see the best of Chicago!
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