5 OF THE BEST UNIQUE TOURS IN CHICAGO FOR FIRST-TIME VISITORS
Last Updated on 14th May 2025 by Bejal
If you decided on making a trip to The Windy City and are wondering what the best unique tours in Chicago for first-time visitors are, this round-up guide is for you! Based on our own experience, we’ve handpicked a few unique tours in Chicago for first time visitors that we think you shouldn’t miss and will gain some pretty special memories from. All featured tours can be booked directly from this article via our tried and trusted booking partner, Get Your Guide, who have a pretty large range of tours in Chicago.
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Whether you love history, beautiful architecture, awe inspiring views or love to eat your way around a city, read on to find out our top pick tours to make your time in Chicago memorable. After all, a good tour can make or break your time in a city!
Related Article: The Best Photo Locations in Chicago: A City Guide
How to Pick The Right Tours for Your Chicago Visit
There are a number of considerations that need to be taken into account when selecting which tours you’ll want to research. Here are some of our helpful hints when booking
#1. Time of Year Visiting
This can play a big factor on the tours on offer as the winter months when the temperatures are pretty low, its raining or snowing, certain outdoor tours may not be running. Plan your trip according to activities you want to partake in.
#2 Book tours based on your interests
It may sound pretty basic but you’ll definitely get more out of an experience if you are interested in the topic area for example, food, architecture, history. Also consider if there are children in your party and which tours would accommodate them.
#3. Budget
Walking tours are often affordable as they don’t require any transport, therefore keeping costs down.
Length of Tours – Most tours are between two hours to half a day. There are a few that are full day tours in Chicago. It’s best to work out how much time you can allocate to experiences as most expect you to be there at least 15-20 minutes before it starts. If you are only in Chicago for a day, you may want to consider a City Tour with transportation so you can see all the main spots. If you are in the city for a few days, you may want to do a number of tours to spread the time,
#4. Flexibility
When booking tours, always be flexible and allow time in your itinerary for any cancellations and time changes. Bad weather of unforeseen circumstances can lead to changes in planned tours. Many tours now also have options to cancel tours or change times up to a certain time point prior to the tour start time.
#5 Location of Base
To save time on travel as well as making more cost effective choices, always have a look at what tours and activities are available in the area you are staying in.
Related Article: Cool & Unique Boutique Hotels in Chicago
Unique Tours in Chicago for First Time Visitors
Read on for a selection of some of our recommended tours covering architecture, history, the transit system, street art and food.
Chicago River Architecture Cruise
If there is just one tour that you do in Chicago, let it be the Chicago River Architecture Cruise! You don’t have to be a big architecture fan to enjoy this experience as it’s a lovely relaxing way to spend 1.5 hours, and allows you to see the city from an alternative prospective.
This tour is lifted by the live fun guides on board who with their knowledge of history and the area, help navigate the time through the beating heart of the city via all three branches of Chicago River. You’ll learn about the 130 year long history behind the Chicago skyline by taking a seat on the open air deck or the climate controlled inside seated space. Refreshments are also available should passengers want to accompany the trip with drinks.
The cruise follows a set route where passengers learn about the history of the earliest skyscrapers such as the Wrigley Building, The Tribune Tower, The Willis Tower, The Merchandise Mart and many more.
The Details
- Length of Experience: 1.5 hrs (get to the meeting point 20 minutes prior to cruise disembarking.
- Tickets: Download the Get Your Guide App to your smartphone to have access to electronic tickets.
- What to Take: sun hat and sunglasses sunscreen, (in warmer weather), rain mac (incase of showers), cards or cash to purchase drinks and snacks onboard, camera.
- Meeting Point: Central long the Riverwalk, around Du salle Street Bridge
- Price Range: $$
Be-lavie Tip: If the weather is on your side, we’d highly recommend sitting on the outside deck. You can walk around to different parts of the boat throughout the tour if you wish and have a chance to capture some great images.
Book Here: The Chicago River Architecture Cruise
Underground Pedway & Downtown Secrets Walking Tour
In our opinion the Underground Pedway & Downtown Secrets Walking Tour, has to be one of the most mysterious and informative tours that should be on your experiences list in Chicago.
The mysterious underground tunnels downtown that keep locals warm & dry in bad weather during the winter months. Wandering the Pedway, through hidden corridors of stained glass and even underground swimming pools, you’ll access interiors that seem to come up out of nowhere!
The tour lasts two hours and is one that will enable you to discover some of Chicago’s gems that you wouldn’t usually know that existed!
Firstly learn about what the Pedway is and how far it spans and then learn of some of the hidden most stunning treasures of the city by walking to points via the Pedway route, both underground and overground. You’ll see some of the best of what Chicago has to offer in this two hour walking tour.
The tour highlights include, the world’s largest Tiffany Dome at the Chicago Cultural Centre, Macy’s Tiffany Stained Glass Ceiling as well as The Chicago Picasso sculpture, to mention a few.
The Details
- Length of Experience: two hour walking tour (arrive 15 minutes prior to start time).
- Tickets: Download the Get Your Guide App to your smartphone to have access to electronic tickets.
- What to Take: sun hat and sunglasses (in warmer weather), rain mac or umbrella, (incase of showers), comfortable shoes, and a camera.
- Not Suitable For: Those with mobility concerns.
- Meeting Point: Downtown location near Millennium Park.
- Price Range: $$
Be-lavie Tip: If during your trip you don’t get a chance to grab the best photos of the Tiffany glass dome or other points of interest, this guide introduces to the locations so plan to head back the next day. The early mornings and late afternoons can be pretty good for less crowds and visitors.
Book Here: The Pedway & Downtown Secrets Walking Tour
Offbeat Guided Street Art Tour
If you love scoping out street art as much as we do, then this Offbeat Guided Street Art Tour, is the perfect two hour walking activity any time of year, as long as you come prepared for the weather.
This guided tour is almost like a colourful celebration of Chicago’s street art through some of the most eclectic neighbourhoods such as Bucktown, Logan Square and Wicker Park.
The tour guide gives a captivating commentary on the street artists, their styles of art as well as what the future holds for street art and graffiti writing in Chicago as a whole.
Often referred to as Chicago’s living canvas, we learnt that Chicago is in fact home to some of the best world renowned graffiti writers. You may even be lucky enough to see art being created on your visit if one of the artists is finishing off.
The tour highlights the talent of artists, it’s funny how much of the artwork is located right beside you but you don’t always see it if you don’t know exactly were to look.
The Details
- Length of Experience: two hour walking tour (arrive 15 minutes prior to start time).
- Tickets: Download the Get Your Guide App to your smartphone to have access to electronic tickets.
- What to Take: sun hat and sunglasses (in warmer weather), rain mac or umbrella, (incase of showers), comfortable shoes, and a camera.
- Not Suitable For: Those with mobility concerns.
- Meeting Point: Disclosed at time of booking with Google Map location (close to L station).
- Price Range: $/$$
Be-lavie Tip: Remember to buy a ticket for the “L” as that will make it easier to get to the start location of the tour. After the tour it’s great to hang out in these areas a little longer and explore. As well as cool eateries, you may even stumble upon some more street art that was missed off in the tour!
Book Here: The Offbeat Guided Street Art Tour
Secret Food Tour of Chicago
Ok so isn’t everyone a kind of a foodie? I mean we all love food, right? Being a bit of a big foodie scene spot, of course there are quite a few great food orientated tours.
This guided Secret Food Tour Of Chicago is a three hour in duration and you will not leave hungry! Foodie tastings are intertwined with the history of how the local speciality became a much loved addition to Chicago’s foodie list. You’ll also get some orientation and little gems of facts about places you pass by whilst on the tour. The guides always have a wealth of local knowledge and are uplifting with their personality and captivating story telling.
There are six different food stops in the Loop district that define Chicago for it’s culinary spots! You’ll be tasting the famous Deep Dish Pizza, special Garrett Popcorn, Chicago style hotdogs, Italian sandwiches, the Original Brownie and a secret dish inside the Willis Tower!
The Details
- Length of Experience: three hours walking tour (arrive 15 minutes prior to start time).
- Tickets: Download the Get Your Guide App to your smartphone to have access to electronic tickets.
- What to Take: :comfortable shoes, camera, all-weather clothing.
- Not Suitable For: Those with mobility concerns and wheelchair users.
- Meeting Point: Within the Downtown Loop area.
- Price Range: $$
Be-lavie Tip: Let your guide know if you are vegetarian so they can make arrangements for alternative versions of the food.
Book Here: The Secret Chicago Food Tour
Related Article: Where To East The Best Vegetarian Friendly Food in Chicago
Check-Out Some Other Great Food Tours in Chicago
Chicago Elevated Architecture Walking Tour
If you are fascinated by the “L”, Chicago’s overground train system, coupled with a helping of architecture and history, this is a pretty unique tour that you have to book!
This two hour Chicago Elevated Architecture Walking Tour gives an interesting perspective of the elevated trains and station platforms through the history of the ‘L’ system and how it fits in around the major architectural giants and skyscrapers of The Loop.
Absorb the live commentary with a local guide as you learn of the first train back in 1892 and how the overground ‘L’ s truly one of the single most defining features of Chicago. The ‘L’ is more than 20 feet tall so riding on it gives some fantastic views of the downtown skyline. Of course you will get the chance to ride the trains for yourself and see what all the hype is about, well worth it by the way!
Once you arrive for the tour at the meeting point, you will be issued with a Ventra ticket for the ‘L’ trains.
The Details
- Length of Experience: two hours in length including riding the L and walking.
- Tickets: Download the Get Your Guide App to your smartphone to have access to electronic tickets.
- What to Take: :comfortable shoes, camera, all weather clothing.
- Not Suitable For: Those with mobility concerns and wheelchair users.
- Meeting Point: Chicago Architecture Center.
- Price Range: $/$$ (fare to ride Chicago’s “L”).
Be-lavie Tip: As you’ll be getting a Ventra card for the day, try out the “L” all by yourself with the Chicago Transit System maps and go and explore the city neighbourhoods further!
Book Here: Chicago Elevated Architecture Walking Tour
Related Article: A Sustainable Guide To Chicago, How To Be More Mindful
Unique Tours in Chicago For First Time Visitors FAQs
Do you need to tip your tour guides in Chicago?
Tipping and gratuities is the culture in the USA. If you feel your guide did an exceptional job (trust us, they will do an outstanding job), feel free to show your appreciation by tipping 20% per person if you feel comfortable with this.
Which Season is Best to Access the Maximum Number of Tours?
We would definitely say, Spring, Summer and Autumn as this way you can do many walking tours and the weather won’t be restrictive. With the bad weather in the winter, especially with snow and gusty winds plus rain, it’s still possible to book tours of course but you may be a little more restricted with photos and views.
Ideally How Many Days Should I spend in Chicago?
To comfortably see most of the points of interest, get a real taste of the city by booking some of the aforementioned tours, we’d recommend three to five days in Chicago.
What is the One Tour all Tourists Need to do if short of Time?
This would be the Architectural River Cruise. It’s a must do activity when in the city.
Can I Change My Mind about the Tour I’ve Booked?
Get your Guide has free cancellation policy prior to 24 hours of the activity for a full refund. They also have a ‘reserve now, pay later’ incase you need more flexibility with your plans.
Are Tours Wheelchair Accessible?
This information is available at the time of booking tours but many of the walking tours are unfortunately not wheelchair accessible due to the scope of the area covered. We feel this is an area that needs to be looked into more globally and not just in Chicago.
Unique Tours in Chicago For First-Time Visitors: Round-Up
This round up of unique tours in Chicago for first time visitors is a wonderful way to get a taste for the city and learn about it’s history through the eyes and experience of the knowledgeable local guides. The tips to consider when selecting activities for yourself or your party of traveler’s will help in the initial planning stages as should the flexibility of booking arrangements. It’s best to make itineraries that are flexible incase tours need to be moved due to unforeseen circumstances, which are generally very rare in our experience.
We hope the information in this guide inspires you to get to know more about the featured local activities in Chicago, which really do give an authentic insight into the history, architecture, transport and food of the United State’s third largest city.
Related Articles
- The Best Photo Locations in Chicago: Ultimate City GUide with Map & Itineraries
- The Best Cool & Unique Boutique Hotels in Chicago
- Where To Eat The Best Vegetarian Friendly Food In Chicago
- The best coffee shops in Chicago for vegetarians and vegans.
- A Sustainable Guide to Chicago: How To Be More Mindful
Resources To Help Plan Your Trip
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Hotels: Choose from a wide range of accommodation with BOOKING.COM
Trains: Get the best available options with TRAINLINE & rail passes in Europe with OMIO
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Car Hire: Compare, search & secure the best vehicle to suit your needs with RENTALCARS.COM
Activities: Personalise your travel with top destination experiences with GET YOUR GUIDE & VIATOR
Shopping & Reading: A one-stop online shop for all your travel shopping needs, including travel guides AMAZON
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