15 Best Tours In Chicago Worth The Money

Are you wondering which guided tours in Chicago you really must go on? You are in the right place.

In this article, I will walk you through what to see in Chicago and tell you which tours in Chicago are worth the money.

There is so much to see and do in Chicago, It is an amazing city. It’s an innovative, vibrant city that mixes the modern and the past seamlessly. 

The culture, architecture, pizza, and somewhat shady past have all made this place famous and a must-visit Midwest city destination. 

But what if you are short on time and want to make the best of your time here? Well, the best way to make the most out of your time in Chicago is to take some of the Chicago tours on offer. 

Whatever you like there is a tour for it and the experienced guides take the second-guessing out of sightseeing. 

In this list of tours in Chicago, I have chosen some diverse and interesting options for you that I feel will keep most people entertained.

From group tours to private tours, from boats to speakeasies I’ve covered them all. 

So if you want to take the stress out of touring in Chicago then maybe book one of these tours and let someone else guide you. 

Here are the best tours in Chicago I have picked for you. Pull up a chair and let me walk you through an easier way to see the Chicago attractions.

15 Best Tours In Chicago Worth The Money

Chicago: 1.5-Hour Romantic Sunset Cruise

This Chicago sunset cruise is perfect if you are looking for romantic Chicago date night ideas.

This Chicago: 1.5-Hour Romantic Sunset Cruise is a perfect way to spend some time with your significant other.

You start your sunset cruise on the Chicago River at Michigan Avenue then make your way along the main branch of the river towards Lake Michigan.

The vessel then goes through the locks and cruises along  Lake Michigan. 

there are so many places to stay in Chicago along Lake Michigan.

As the sun sets you are treated to the most beautiful view of the Chicago skyline with that beautiful sunset glow.

You can also purchase snacks and drinks on board and I don’t know about you but sunset and champagne sound perfect. 

There is a short narration at the beginning of the cruise but most of the cruise is just about admiring the view no narration is needed. 

The cruise last 1 ½ hours and you will see many Chicago attractions. You can sit on the open deck or inside whichever you prefer but the deck has to there best right?

This really is one of the best Chicago tours for couples.  

Book : Chicago: 1.5-Hour Romantic Sunset Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

If you are looking for a Chicago architectural boat tour then this Chicago River: 1.5-Hour Guided Architecture Cruise will be perfect for you.

If you have come to Chicago in search of architectural Chicago sights then you will love this tour.

Here you can experience the Architecture from the top deck or inside as you travel along the main River and its north and south branches.

Things you will see include Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, and mid-century skyscrapers like the Mies Van der Rohe AMA Building among others. 

The guides are experienced and the narration gives you all the information you need. The tour lasts 75 minutes and if you are short of time and want to see a lot this is the boat ride in Chicago for you. 

Book Here: Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

There are so many great restaurants in Chicago it can be hard to know where to start. This Chicago Food Tasting: 2.5-Hour Guided Walking Tour is a great way to get a taste of Chicago.

I don’t know about you but everywhere I go I want to do a food tour, I feel like food tells you so much about a city, and this Chicago food tour is no exception. 

This 2 ½ hour walk around downtown introduces you to some of the city’s top sites. You will get to enjoy deep-dish pizza, Italian pastries, a Chicago-style hot dog, and a classic Italian beef sandwich. 

You will also see some of Chicago’s historic buildings along the way which course will be pointed out to you. 

The pace is leisurely, the food great, and some of the places iconic what more could you want? 

Book Here: Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Chicago: 45-Minute Private Helicopter Flight for 1-3 People

If you are looking for Helicopter tours in Chicago then this one is perfect. Chicago: 45-Minute Private Helicopter Flight for 1-3 People shows you the city from a different perspective.

You will see all of the important Chicago sights from a vantage point most others don’t get to enjoy. 

The McCormick Place, Soldiers Field, Wrigley Field, Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan are all highlights.

You depart from Schaumburg Regional Airport and the flight last 45 minutes. It’s a private flight with a maximum of three passengers.

The commentary is perfect, and in summer if you want you can fly with the doors off.

Book Here: Chicago: 45-Minute Private Helicopter Flight for 1-3 People

Chicago: Treasures Of The Golden Age Walking Tour

If your idea of getting to know the city is more from the ground than up in the air then how about a Chicago walking tour?

Chicago: Treasures of the Golden Age Walking Tour covers the most significant Chicago attractions.

The guides are trained by the Chicago Architecture Center and the tour focus on great cultural buildings from the late 19th and early 20th centuries.

So expect to see lots of Beaux Arts, neo-Georgian and neo-Gothic.

And you will get to go inside some of the buildings too. Highlights include Chicago Cultural Center, home to the world’s largest Tiffany dome.

And the iconic Marshall Field department store, now Macy’s on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

This just seems a beautiful way to see the city and is one of the best tours in Chicago.

Book Here: Chicago: Treasures of the Golden Age Walking Tour

Chicago: Mob and Crime Bus Tour

If you are looking for a Chicago gangster tour the Chicago: Mob and Crime Bus Tour will be perfect for you.

When in Chicago this just has to be done right? This tour in Chicago takes you into the underworld of criminals and gangsters all in the confines of a luxury bus. 

On this tour, you will learn about some of the world’s most famous criminals, mobsters, and gangsters and see some of the famous Chicago crime scenes. 

This interactive tour will teach you all about Al Capone, the Untouchables, and the Chicago Mob.

Also John Dillinger, Terrible Tommy O’Connor, H. H. Holmes, the Chicago Black Sox, Leopold, Loeb, bank heists, Cap George Streeter, and more.

If you have an interest in all things crime, murder, and the gangster underworld you are just going to love this Chicago activity.  

Book : Chicago: Mob and Crime Bus Tour

Chicago: Windy City Ghosts Haunted Walking Tour

And now we move from gangsters to ghosts. This Chicago ghost tour goes through Northside Chicago and visits some of the city’s most haunted locations.

If you love a scare Chicago: Windy City Ghosts Haunted Walking Tour is for you.

The tour is laced with tales of spirits, people long forgotten and ghosts still making their presence known.

Will you see the Victorian woman in white who is seen in the bathroom mirrors at Lincoln Park Zoo? 

On the standard tour, you visit eight locations but this can be expanded to visit 12. Personally, I’d opt for all 12 but I love a good ghost story. 

This is the best tour in Chicago if you love all things scary.

Book: Chicago: Windy City Ghosts Haunted Walking Tour   

Chicago: City Minibus Tour With Optional Architecture Cruise

This is a great sightseeing Chicago bus tour if you prefer to see the city in comfort.

Chicago: City Minibus Tour with Optional Architecture Cruise also you to see the sights of Chicago in comfort.

You begin in the heart of downtown Chicago and go from there. There are too many stops to mention on this tour but let’s just say it’s a lot.

You will see the world’s first skyscrapers, see a beautiful lobby designed by Frank Lloyd Wright and visit the fancy Gold Coast nightlife area where the original Playboy Mansion is. 

This tour of Chicago lasts a couple of hours and there is an option to extend with a 75-minute cruise of all three branches of the Chicago River.

This is one of the best tours if you are not sure what to see in Chicago as it shows you so much.

Book:Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: Fireworks Cruise With Lake Or River Viewing Options

If you are after a Chicago boat tour/river cruise then Chicago: Fireworks Cruise with Lake or River Viewing Options offers something a little bit different.

This boat cruise allows you to see the amazing fireworks display off Navy Pier from the boat. 

There is a short narration on some history and architecture at the beginning of the cruise then it’s all about fireworks, which you can watch outside on the deck or inside. 

There is a short and long version of this boat ride in Chicago. The longer one lasts 2 ½ hours the shorter about an hour so choose which one feels best for you.

In the longer version, you go through the locks and into Lake Michigan for an incredible view of the city. 

Book Here: Chicago: Fireworks Cruise with Lake or River Viewing Options

Chicago: History, Culture And Architecture Walking Tour

If you are looking for a Chicago architectural tour then the Chicago: History, Culture and Architecture Walking Tour is perfect for you. This is a great way to go sightseeing in Chicago.

The tour starts under the dazzling marquee of the Chicago Theater and heads off into the city from there. 

You will get to walk the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. 

On this tour, you go inside City Hall sample some Chicago-style popcorn, stroll along the Chicago Riverwalk, and much much more.

 Notable sites are the Wrigley Building and the incredible Chicago Tribune building, Millennium Park, and many more. 

Oh, and you also go chocolate tasting if you needed any more convincing. It’s a perfect enhancement to your Chicago Visit.

Book: Chicago: History, Culture and Architecture Walking Tour

Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

For the ultimate in sightseeing, the hop-on-hop-off Chicago is a perfect way to tour Chicago.

Chicago: Big Bus Hop-on Hop-off Sightseeing Tour is a double-decker bus that gives you a great vantage point to experience all of the city’s impressive landmarks. 

Sights the bus takes in include the John Hancock Center, the Willis Tower, the Wrigley Building, and the famous Magnificent MileMichigan Avenue Bridge over the Chicago River.

You can hop on and off as many times as you want so you can explore the sights at your own pace.

Tickets last for 24/48 hours so It’s a great way to help you get around the city to see everything. This is touring in Chicago at its best.

Book: Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

f you want to be treated like a star for the evening on your Chicago visit then how about a private speakeasy tour? 

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour is a real delight for those that want to feel a little bit special.

You visit the speakeasies that have been open since the Prohibition Era in the 1920s many still as original as the day they were built.

You enter via secret entrances and enjoy the same cocktails the infamous gangsters in the area loved. 

If you love the 1920s and all its history then this tour of Chicago is for you.

You travel around with a young professional guide who advises you on the best drinks and you are chauffeured to the places in luxury transportation. 

If you wondered what it feels like to be a famous gangster this is your time. 

Book: Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Chicago Underground Donut Tour In Chicago

I know a donut tour might seem a little odd but honestly, the Chicago Underground Donut Tour is perfect for a group of friends.

The tour is in the downtown area and you get to try donuts from Stan’s Donuts, Do-Rite Donuts, and Firecakes Donuts, which are true donut institutions in this area, 

The tour takes two hours and if you don’t know anything about donuts yet you will by the end of this tour, you also be pretty full too.  

So if you are after something a little different then this might be perfect for you. This is a great Chicago activity.

Book Here: Chicago Underground Donut Tour

Amazing Lakefront Segway Tours Of Chicago

Fancy sightseeing in Chicago in a relatively new form of transport then how about a Segway?

On the Amazing Lakefront Segway Tour of Chicago, you will be gliding around the streets and parks of Chicago without a care in the world. 

You will uncover quirky facts about the city and have fun at the same time.

The tour starts with a training session before you make your way around Millennium Park and continue to Grant Park to stop and admire the famous Buckingham Fountain

You also ride to Museum Campus where you get a great view of the Chicago skyline and beautiful lakefront. This is a great fun way to see the city and if you have teens they will love this. 

This is one of the best tours in Chicago and a great way to see the sights of Chicago and experience some of the breweries in Chicago.

Book Here: Amazing Lakefront Segway Tour of Chicago

Chicago: Night Tour With Willis Tower Entry & Skyline Cruise Is One Of The Best Tours In Chicago

For the ultimate tour, you might what to try the Chicago: Night Tour with Willis Tower Entry & Skyline Cruise.

You get to see the Windy City’s most prominent sites, watch the Buckingham Fountain night light show, enjoy a Chicago skyline cruise, and go to the top of the iconic Willis Tower.

You really do get everything with this tour. The first stop is the Willis Tower, the tallest building in the Western Hemisphere.

You get to go to the top and take in the view. You also see over 40 iconic landmarks on this cruise. This is one of the coolest things to do in Chicago at night!

Then you go on a night skyline cruise and see the city all lit up. After that, you get to watch the spectacular light and music display at Buckingham Fountain.

It’s the perfect Chicago tour if you are short on time.

Book: Chicago: Night Tour with Willis Tower Entry & Skyline Cruise.

Packing List For Doing Tours In Chicago

If you are searching, here are some tips on how to pack lightly when packing to take tours in Chicago.

A concealed travel pouch may be one of the most important items you bring along when touring Chicago.

It is always important to protect your personal information. Identity thieves are everywhere.

This unisex RFID blocking concealed travel pouch is lightweight and comes in several colors. It has lots of organization to give you peace of mind.

If you have a pouch already that does not come with the RFID protection, as I do, these RFID sleeves are the perfect solution.

This configuration comes with enough credit card sleeves that the entire family would be protected. They are slim too, so they will easily fit into your pouch or wallet.

If you are planning on taking a lot of pictures with your phone you will definitely want to consider an external charging battery. This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

It can be used on a variety of phones, not just an iPhone like I have. And wow is it fast!

I like that it holds its charging capabilities for several uses so I do not have to worry about it while out and about, and if I forget to recharge it at night, it will still be good to go the next day.

My daughter gifted me with this FugeTek selfie stick and tripod setup for my birthday. I absolutely love it! It is made of lightweight aluminum and is so easy to use.

It has Bluetooth connectivity and is a breeze to use for taking selfies with family and friends when taking Chicago tours.

Hydration is so important when traveling. You want to remain hydrated throughout your travels to support your immune system which in turn will be stronger to fight off any germs you will encounter during your travels.

You will want to bring your own refillable water bottle with you.

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect for hiking and it fits nicely in the pocket of a backpack.

When filled with water, it is not too heavy to carry. And the charcoal filter ensures fresh clean water whenever you fill the Bobble.

Perhaps you are traveling a long distance and packing space is a premium in your suitcase, or in your car.

Then this set of collapsible silicone foldable water bottles would work well for you. Would not take up much space at all.

You will want a backpack or daypack with you to store snacks, your water bottle, phone, extra clothes, etc.. then this foldable water-resistant backpack would be great.

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As you can see when it comes to tours in Chicago there are so many to choose from. Tours are a great way to see the Chicago sights. And a perfect way to enhance a weekend in Chicago!

And if you want to start your day right, check out some of the best places for breakfast in Chicago!

Whichever of these Chicago tours you choose I hope you have a great time and please come back and tell me all about it.