5 UNIQUE TOURS IN CHICAGO FOR FIRST-TIME VISITORS
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Last Updated on 2nd September 2026 by Bejal
Planning your first trip to Chicago and wondering which tours are actually worth your time? While the city offers plenty of classic sightseeing experiences, some of its most memorable adventures are the ones that go beyond the typical tourist trail.
From world-famous architecture cruises and fascinating gangster tours to food-focused experiences and hidden local gems, Chicago has no shortage of unique ways to explore the city.
In this guide, we’ve rounded up the best unique tours in Chicago for first-time visitors so you can experience the city’s history, culture, and personality while making the most of your trip. For us, the architectural tours from the Chicago River will always be win for their exceptional perspective and educational commentary.
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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!
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:
- 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.
- 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.
- 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,
- 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.
- Location of base – Location of BasTo 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. There are so many cool and unique boutique hotels in Chicago .
Search hotels & make sightseeing easier by staying near Chicago’s most popular attractions.
Here are some of our recommended tours covering architecture, history, the transit system, street art and food.
#1. 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.
We we loved the tour: It was a pretty warm spring day during our visit and we sat up on deck which allowed us to get up close and perosnal with the stories being told by the guide as well as be in prime position to take great photos.
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.
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.
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: $$
#2. 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.
Why we loved this tour: It feels very secretive and the guides storytelling was exciting as every corner we turned told a hidden story of the city, it’s art and history.
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.
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.
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: $$
#3. 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.
What we loved about the tour: the fact that we moved away from the downtown area and were in more local territories which seemed cool. The street art was something we probably couldn’t have found easily as some of it is hidden behind L stations and down local streets in residential neighbourhoods.
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.
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!
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: $/$$
#4. Secret Food Tour of Chicago
Ok so isn’t everyone a kind of a foodie? I mean we all love food, right? Being a bit of a big foodie scene spot, of course there are quite a few great food orientated tours.
This guided Secret Food Tour Of Chicago is a three hour in duration and you will not leave hungry! Foodie tastings are intertwined with the history of how the local speciality became a much loved addition to Chicago’s foodie list. You’ll also get some orientation and little gems of facts about places you pass by whilst on the tour. The guides always have a wealth of local knowledge and are uplifting with their personality and captivating story telling.
Why we enjoyed this tour: It was a fab round-up of the local food and drink eaten in the city in a concise time frame with plenty of tastings to want us reeling for more. The guides also provided vegetarian alternatives to food for non meat eaters.
There are six different food stops in the Loop district that define Chicago for it’s culinary spots! You’ll be tasting the famous Deep Dish Pizza, special Garrett Popcorn, Chicago style hotdogs, Italian sandwiches, the Original Brownie and a secret dish inside the Willis Tower!
Be-lavie Tip: Let your guide know if you are vegetarian so they can make arrangements for alternative versions of the food. There are so many vegetarian-friendly places to eat in Chicago!
The Details
- Length of Experience: three hours walking tour (arrive 15 minutes prior to start time).
- Tickets: Download the Get Your Guide App to your smartphone to have access to electronic tickets.
- What to Take: :comfortable shoes, camera, all-weather clothing.
- Not Suitable For: Those with mobility concerns and wheelchair users.
- Meeting Point: Within the Downtown Loop area.
- Price Range: $$
Other highly rated foor tours in Chicago
#5. 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! Using the L is also one of the more sustainable ways to explore Chicago.
Why we booked this tour: It’s quirky yet fascinating to learn about the overground architecture. The annecdotes kept us entertained as did teh stores of the L. The tour guide also made the tour extra special with his enthusiasm and knowledge of the Chicago’s unique architectural facets.
Once you arrive for the tour at the meeting point, you will be issued with a Ventra ticket for the ‘L’ trains.
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!
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”).
Quick Snapshot: How We Rate The Tours If You’re Short of Time
The star rating denotes the priority we’d give to tours based on their length of time, information and giving an overall feel for the city. If you all of the tours are onces we’d recommned for their originality to Chicago and historical value.
| Chicago Tour | Be-lavie Rating (Star Rating *) |
|---|---|
| Chicago River Architecture Cruise | ***** |
| Secret Food Tour of Chicago | **** |
| Underground Pedway & Downtown Secrets Walking Tour | *** |
| Offbeat Guided Street Art Tour | ** |
| #5. Chicago Elevated Architecture Walking Tour | * |
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.Â
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.Â
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.Â
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 Round-Up
We think Chicago is a city that offers unique tours for first-time visitors with the opportunity to uncover its deep stories, culture, and character in a more meaningful way. Whether you’re cruising along the Chicago River, exploring world-famous architecture, sampling local food favourites, or discovering a local neighbourhood , each experience provides a unique perspective on the Windy City through the expertise of passionate local guides.
The beauty of these tours is that they cater to a variety of interests and travel styles, making it easy to build an itinerary that reflects your own personal interests. When planning your visit, remember to book popular experiences in advance, allow some flexibility in your schedule, and leave room for spontaneous discoveries often the most memorable moments of any trip.
Now it’s time to start planning your Chicago adventure. Save this guide for later, compare tour options, and secure your favourite experiences before they sell out. With its rich history, iconic architecture, diverse food scene, and vibrant culture, Chicago is a city that rewards curiosity, and these unique tours are the perfect introduction to everything it has to offer.
We’d suggest reading the below related articles (written with our expertise of visiting 4 times over a few years), which will help with crafting your own pace of itinerary for Chicago.
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- 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 Chicago Trip
- Flights: Search & Book the best flight options through SKYSCANNER
- Travel Insurance: An absolute must-have! Check rates on SAFETYWING
- Hotels: Choose from a wide range of accommodation with BOOKING.COM
- Trains: Get the best available options for rail passes with OMIO
- Buses: Scope out the best coach travel deals in Europe with OMIO
- Car Hire: Compare, search & secure the best vehicle to suit your needs with DISCOVER CARS
- Activities: Personalise your travel with top destination experiences with GET YOUR GUIDE & VIATOR
- Shopping: A one-stop online shop for all your travel shopping needs, including travel guides AMAZON
- Traveller Reviews: Check unbiased reviews for accommodation, tours and restaurants at TRIPADVISOR
- Travel Resources: Access Be-lavie’s full-list of tried and tested PARTNERS
- eSIM: Keep roaming charges low with an eSIM from AIRALO
À bientôt
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