Tours In Chicago: 15 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. 

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.

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.

Tours In Chicago: 15 Worth The Money

Chicago: Romantic Cruises

Chicago cruises are perfect if you are looking for romantic Chicago date night ideas.

You start your sunset cruise on the Chicago River at Michigan Avenue then toward 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.

You can also purchase snacks and drinks on board. Sunset and champagne sound perfect together. 

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

You will see many Chicago attractions. You can sit on the open deck or inside whichever you prefer.

These are fun Chicago tours for couples.  

Book Here: Chicago: 1.5-Hour Romantic Sunset Cruise

Book Here: Guided Sunset Cocktail & Architecture Tour

Book Here: 90 Minute River & Lakefront Cruise at Night

Chicago River: Guided Architecture Cruises

One of the best things to do in Chicago is take an architectural cruise along the Chicago River.

You will love these tours if you have come in search of architectural Chicago sights.

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

The guides are experienced and the narration gives you plenty of information.

The tours last around 75 minutes so if you are short of time and want to see a lot, this is a great option for you.

Book Here: Architecture River Cruise Skip-the Ticket-Line Tour

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

Book Here: 45-Minure Family-Friendly Architecture River Cruise

Chicago Food Tasting: 2.5-Hour Guided Walking Tous

There are so many great restaurants in Chicago it can be hard to know where to start.

Food tells you so much about a city, Chicago food tour options are no exception. 

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 iconic places what more could you want? 

Book Here: Downtown Donut Tour With Tastings

Book Here: Classic Food Walking Tour With Bike or Kayak Rental

Book Here: Ultimate Food Walking Tour with Tastings

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

If you are looking for Helicopter tours in Chicago 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 the important Chicago sights from a vantage point most others don’t. 

Highlights include McCormick Place, Soldiers Field, Wrigley Field, Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan.

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

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

Chicago Walking Tours

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

An experienced guide will walk you through iconic locations throughout the city.

This seems a beautiful way to see the city and are some of the best tours in Chicago.

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

Book Here: Magnificent Mile Walking Tour

Book Here: Secret Interiors Architectural Walking Tour

Tours In Chicago: Gangster Tours

When in Chicago this just has to be done. You want to delve into the underworld of Chicago criminals and gangsters right? 

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

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

Book Here: Chicago: Mob and Crime Bus Tour

Book Here: Gangsters and Food Tasting Walking Tour

Book Here: Gangsters and Ghosts Guided Walking Tour

Tours In Chicago: Windy City Ghosts Haunted Walking Tours

And now we move from gangsters to ghosts.  Chicago ghost tours visit some of the city’s most haunted locations.

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? 

These are the best tours in Chicago if you love all things scary.

Book Here: Chicago: Windy City Ghosts Haunted Walking Tour   

Book Here: Medieval Torture Museum & Ghost Hunting

Book Here: Mob And Crime Bus Tour

Chicago: City Bus Tours

There are great sightseeing Chicago bus tours if you prefer to see the city in comfort.

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

These Chicago tours last a couple of hours

Book Here: Hop-on Hop-off sightseeing Tour by Open-top Bus

Book Here: Panoramic Sunset Tour with Live Guide

Book Here:Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: Fireworks Cruises

Boat cruises allow 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 cruises and it’s all about fireworks, which you can watch outside on the deck or inside. 

There are short and long versions of the 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 incredible views of the city. 

Book Here: Fireworks Cruise with 3D Glasses and Music

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

Book Here: Fireworks Buffet Dinner Cruise on Lake Michigan

Chicago: History, Culture, And Architecture Walking Tours

Walking architecture tours are a great way to see Chicago attractions.

Some tours begin under the dazzling marquee of the Chicago Theater and head off into the city from there. 

You may 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. 

You could go inside City Hall to sample some Chicago-style popcorn or stroll along the Chicago Riverwalk.

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

Book Here: Must-See in Chicago: Architecture, History and Culture Tour

Book Here: Chicago: History, Culture, and Architecture Walking Tour

Book Here: Secret Interiors Architectural 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.

A double-decker bus gives you a great vantage point to experience 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 Here: Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

Book Here: 2-Day Hop-on Hop-off Tour & 360 Chicago Admission

Cocktail Tours in Chicago

Be treated like a star for the evening on your Chicago!

Visit some 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. 

Or ride along the river at sunset with a cocktail!

Cocktail tours in Chicago never disappoint. 

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

Book Here: Chicago River Guided Sunset Cocktail & Architecture Tour

Book Here: Prohibition speakeasies Bus Tour or Walking Tour

Chicago Tours: Donuts and Ice Cream

If you are a foodie looking for unusual food tours in Chicago, I have some options!

Tours are mostly in the downtown area and if you did not know about donuts or ice cream before, you will now!

Book Here: Chicago Underground Donut Tour

Book Here: Chicago Museum of Ice Cream

Book Here: Downtown Donut Tour With Tastings

Amazing Lakefront Segway Tour Of Chicago

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

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: Willis Tower Skydeck Wows!

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 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!

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

Look Here: Willis Tower Skydeck and Ledge Ticket

Look Here: Explorer Pass with choice of 2 – 7 Attractions

Book Here: 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 to take tours in Chicago.

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.

These RFID sleeves are another option.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

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

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect and not too heavy.

And the replaceable carbon filter ensures fresh clean water whenever you fill the Bobble.

This foldable water-resistant backpack would be great when taking any of the tours!

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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.