Small-Group Tour of Chicago Neighborhoods - North and South Side | 4 hours 30 minutes

43 Reviews | Chicago
From $125.00 per person Lowest Price Guarantee
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2
Youth (11-17) Minimum: 0, Maximum: 5
0
Child (3-10) Minimum: 0, Maximum: 5
0
Infant (0-2) Minimum: 0, Maximum: 5
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Free Cancellation For a full refund, cancel at least 24 hours before the scheduled departure time.
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Inclusions / Exclusions

  • Mobile ticket
  • Offered in: English
  • Phone charging port.
  • Headphones to hear guide.

Overview

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighborhoods in Chicago. Some tours show 1 or 2 neighborhoods, we travel through the South Side, North Side, Southwest, Northwest and a portion of Downtown showing more then 10 neighborhoods and attractions.

Pickup points

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Pickup details

If the schedule allows, pick up from airport is an option for an additional $60, the price of an Uber ride. ... Read more â–Ľ

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Meeting points

The front entrance of the Chicago Theater. **If you staying at a Chicago downtown hotel, we will pick you up from the hotel.

End point

This activity ends back at the meeting point.

Itinerary

  • Hyde Park (Pass By)

    Travelers will see the neighborhood and home of 44th President of the United States and plaque where Michelle Obama was 1st kissed! Travelers will tour the college campus of The University of Chicago that attracts students from around the world where many remain post graduation in the historical Hyde Park. In addition to the medical professionals from The University of Chicago Medicine and the local residents, the neighborhood is a true melting pot. With real estate in the area ranging from multi million dollar homes to $600 monthly apartments, Hype Park is a tour favorite!

  • Lincoln Park (Pass By)

    Travelers will see the historical Du Paul University and its breathtaking beautiful neighborhood! The beauty of Lincoln Park rivals any neighborhood in America with its traditional to modern, frame to brick homes, shops, restaurants and so much more!

  • Gold Coast (Pass By)

    Travelers will be amazed by Chicago’s beautiful Gold Coast neighborhood and parks.

  • Wrigley Field (Pass By)

    From the tour van, tourist will see the city’ neighborhoods and parks including Wrigley Field (Go Cubs!)

  • Bronzeville (Pass By)

    Travelers will learn Bronzeville’s history of African Americans leaving the south and getting off at the last stop in Chicago. While some stopped in St. Louis and other cities, many stayed in until the last stop and knew to get off when the conductor yelled “I don’t care where you go but you have to gotta get outta here”! Travelers will learn of the naming of Bronzeville in relation to African American skin as will as see Pilgrim Baptist Church that many refer to it as the birth of gospel music! With Bronzeville being revitalized, travelers will see the new next to the old. Travelers will see a slice of black life.

Sample Menu

Additional Info

  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • FOR GROUPS OF 12 OR MORE TRAVELERS, 7 DAYS NOTICE IS REQUIRED.

Free Cancellation

August 27100% refund
August 28No refund

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Traveler Photos
Reviews

4.6

43 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews
  • 5 stars
    35
  • 4 stars
    3
  • 3 stars
    2
  • 2 stars
    0
  • 1 star
    3

Reviews by TravelOne travelers

Showing 1-5 of 35 reviews with 5 stars

What a great way to tour Chicago for the first time !

Published on Nov, 2024

Steve was prompt picking us up @ our hotel. He then covered history of the areas we visited in a relaxed, informative manner. We were encouraged to notify him when and if we wanted to stop and take pictures. Also, we were so impressed with this gentleman that we agreed to have him drive us to the airport several days later.

Best guide ever!

Published on Jun, 2024

Steve is the perfect tour guide. He is extremely knowledgeable, plus he’s respectful and polite. I could relax and soak in Chicago in comfort knowing I was in great hands. Plus. I love his long sunroof allowing an enhanced view of everything.

Wonderful personal tour of Chicago as a city

Published on Apr, 2024

Steve took us through neighborhoods from downtown through the extensive South side and up into the North side, always with great running commentary on the history, people, and places in each neighborhood. Thus was exactly what we hoped for. It was even better than expected -because Steve lives and works in Chicago he was able to share personal experiences that made the tour even better. We had a wonderful time!

If you want to see Chicago beyond the Bean, River Walk and Lake do take this Southside tour!!

Published on Jan, 2024

We had been in Chicago for a couple of months and had done all the usual sights. We had a few days remaining and felt there was a big area south we hadn't explored at all. Enter Steve ..... what he doesn't know about the Southside is just not worth knowing. I had no idea just how many famous people were born or spent time in South Chicago. It was such an informative excursion; he drove us all the way down to the Indiana border with a really interesting commentary, identifying all the different neighbourhoods and how they came about. There were lots of stops to take pictures and a nice break in a local coffee shop. I urge you to take this trip which really gave us a much better understanding of the whole of Chicago. Oh.... and those famous people's homes you can see, past and present.... Muddy Waters, Johnny Mathis, the Marx Brothers, Pops Staples, Kanye West, Muhammad Ali, President Obama! Fantastic. Thank you, Steve. We will always remember the three reasons folk from the South travelled to Chicago... JOBS, JOBS AND JOBS!!

Highly recommend tour of Chicago with the Best tour guide!!

Published on Oct, 2023

Steve is Awesome. He is very knowledgeable and passionate about Chicago! Steve has a great sense of humor and makes the tour fun. He took us to popular places as well as places we would have never been able to visit if we hadn’t gone on this tour! There are so many neighborhoods in Chicago and Steve knows them all. I highly recommend taking this tour. He will also pick you up from the airport and take you back for less than an Uber.

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Louise Berg
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