A Walking Tour of Downtown Chicago

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After visiting Chicago in 2012 for the Ryder Cup and only have a little time to explore downtown, we decided that a great way to spend a weekend getaway was to revisit the Windy City. Despite wanting to explore Chicago, we also wanted to take a trip around Lake Michigan, through Indiana and into the state of Michigan as this was another of our states that we had yet to visit.

However, the highlight of this trip had to be our walking tour of downtown Chicago which allowed us to really experience true Chicago and see some of the key landmarks and highlights of this city.

walking tour of downtown chicago

Navy Pier

Driving back from Michigan, we arrived in downtown Chicago around 1:30PM. On a gorgeous Saturday afternoon this is always going to be one of the negative aspects of driving a rental car because parking is either expensive or difficult to find.

We decided to park in the Navy Pier Parking Garage which for $25 was expensive but at least it gives you the freedom of leaving your vehicle there all day. Chicago’s Navy Pier is similar to Pier 39 in San Francisco and is a real hub for entertainment and dining options. Unfortunately, the Pier is currently undergoing renovations although you are still able to explore the Pier.

downtown chicago

The Navy Pier is a great place to look back on the impressive Chicago skyline and take some memorable pictures. You can also take various cruises that go out around Lake Michigan from this location and the River Architecture tour is highly recommended by many though we opted to walk around instead.

There are numerous restaurants and a great food court to choose from at the Navy Pier and we opted for Carnelli’s Deli for lunch. We would highly recommend this to anyone who wants a lighter option but still has a Chicago style feel to it.

Walking Tour – Downtown Chicago

One of the great aspects of Chicago’s downtown area is that you can wander around for hours seeing a variety of different landmarks and genius architectural designs. The image below shows a snapshot of the route we took from Navy Pier as we decided to create our very own ‘Chicago Walking Tour‘.

Chicago Walking Tour

I have highlighted a few of the key spots along the way but this route was a little over 3 miles and well worth taking the time to do. Along this route you will see Chicago’s skyline up close with a variety of beautifully designed skyscrapers but there is so much more to Chicago’s downtown area that just high-rise buildings.

Walking Tour Key


As I have already mentioned the Navy Pier is home to various restaurants including Bubba Gump’s, Jimmy Buffet’s Margaritaville among others.


The Centennial Fountain is a great spot to just go and relax along the river. Throughout the day, the fountain shoots into the river providing a spectacular display for onlookers.

downtown chicago

You can sit and take in the beautiful architecture with some of Chicago’s high-class hotels located on this part of the Riverfront. We spent quite a bit of time here, buying an ice cream from a van parked on the side of the street and just relaxing in the late afternoon Chicago sun!

downtown chicago


Millenium Park is a real hub for tourists and locals alike who want to just relax, work out or check out some of the key landmarks within this park. Home to the Cloud Gate Sculpture and Pritzker Pavilion, this is a really great part of the city worth exploring.

downtown chicago


As we headed back to the Navy Pier, we came across another gorgeous little park in the heart of Chicago – the Lake Shore Park. This is a great spot for people to walk their dogs or take their children on the play area.

downtown chicago

Full credit must be given for the upkeep of this park as tulips and other floral arrangements were neatly maintained in this park.


Of course we didn’t see everything there is to explore in downtown Chicago but this is a really good walking tour if you are interested in seeing all of the key landmarks on foot.

Aside from the fact taking a personal walking tour is free, unlike the architectural river cruise or lake cruise, you will certainly burn some calories which won’t hurt you after sampling some of Chicago’s finest cuisine.

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Chris Boothmanhttps://abritandasoutherner.com
Chris Boothman is the co-founder of A Brit and A Southerner. Born near Manchester, England, Chris moved to USA in 2006 where he soon after met his wife and travel partner in crime, Heather. They have since embarked on an amazing journey of travel as they challenge others to follow in their paths of working full-time but also being able to travel frequently! If you have any questions or comments, please feel free to contact Chris at [email protected]


  1. I really want to go on a walking tour. I have been interested, but it is hard sometimes to find the time. I was supposed to go to Chicago once, but the trip was canceled. I have been through the airport so many times.

    • Angela, you make a great point about time! That is particularly difficult for us given that we are focusing so much on ‘weekend getawaways’ which prevents us from having that crucial time to really explore places. Generally we are speeding around from one spot to another but this time we decided to park our car at the Navy Pier and then just spend the afternoon and early evening wandering around downtown. It worked out pretty well for us as you can see and I would highly recommend it to anyone. Generally that would be one of the major advantages of using public transportation rather than renting a car because the cars can be a hindrance in major cities.

  2. I love Chicago; it’s definitely one of my favorite U.S. cities and one of the few where I feel like it’s totally worth shelling out the money for a CityPass (about $80 and gets you into, I believe, 6 attractions). The Navy Pier is great, and so is the Museum area. You can’t beat the Field Museum and the Shedd Aquarium!

    The next time you head into Michigan, definitely make an effort to go upstate. The northern part of the state is absolutely stunning (Charlevoix, Sleeping Bear Dunes, Mackinac Island, Higgins Lake, the Upper Peninsula).

    Glad you had a good trip!

    • Thanks for the additional information Jessi! The CityPass in NYC was really cool and we think we got good value for money on that one so I can imagine the Chicago version is equally as good. I know that these types of passes are sometimes frowned upon because people think you are forced into seeing the attractions that ‘the guides’ want you to, but the reality is they are a great way to see a city especially for the first time. We all want to see the main landmarks right, at least once in our lifetime!

      I also appreciate the tips on Michigan. I know we didn’t get the ‘real’ Michigan feeling when we headed to Benton Harbor but as time only permitted that quick pit-stop it was at least a way for us to knock Michigan off our US State list. We will however head back there sometime to explore upstate!

  3. Chicago is one of our family’s favourite U.S. cities to visit – I think we have been 7 or 8 times! We spend a lot of time visiting the big attractions like Shedd Aquarium, the Field Museum and the Art Institute but love walking around and enjoying the free outdoor attractions like Millennium Park too. And I don’t think that we have ever been to the city without visiting American Girl Place to shop for dolls! Chicago is a fabulous city and definitely worth a return visit!

    • Thanks for providing some additional spots worth visiting Lisa! It’s always great to hear what other folks like to see and explore in cities around the world and clearly Chicago has a plethora of attractions worth seeing. We will definitely have to check some of those out on our next trip to the Windy City!

  4. Great photos – I love the first one of the domineering skyline and the artistic shot of the tulips – Great colours and composition. Chicago sounds like a great place to visit – It’s not somewhere I have thought about going to in the states, what would you describe as typical Chicago cuisine?

    • Thanks Paul! Whenever you think of stereotypical Chicago cuisine, two things probably come to mind – Chicago style, deep-dish pizza and Chicago Hot Dogs! We experienced pizza but unfortunately our experience was not particularly good so I will defer this to someone else to give a really good spot to sample Chicago pizza. We sampled Lou Malnati’s in Elk Grove but I’m sorry to say the pizza was pretty awful and that’s being kind!

  5. A walking tour sounds great, especially through a city like Chicago I feel like. I’ve only ever been to the airport but the bean looks so cool! Fabulous photos

  6. those are some great photos I saw navy pier, lakeshore park area but I totally missed that fountain its gorgeous. I’ve been to Chicago 3 times already and I love it got some great photos which are on my personal facebook page. thanks for showing me that part of Chicago,

  7. Another informative post, Chris!! I would love to take a walking tour of the windy city. It looks like a place where you can stroll around and enjoy the vibe of the city on foot. The picture of the Cloud Gate Sculpture is incredible – I love the mirror images of the people and the buildings!!

  8. I always créate my own walking tours too or I go on a free walking tour. They are usually really good as they show you different things. Also they are tips based, so the guides usually put a lot of effort into it.

    • This was the first time that we have actually wrote about our ‘self-guided walking tour’ but we tend to do the same thing each time whenever we head to a downtown location. One of our favorites in recent months was in Paris when we explored several of the arrondissements in downtown Paris. It is such a great way to capture the ‘real’ city feeling as opposed to just visiting the main landmarks that a city has to offer.

    • Cheers Gabor, we really appreciate the feedback and hope that this guide will help others experiencing Chicago for the first time. Of course this is not an exhaustive list and there are many more landmarks even in the downtown vicinity that we didn’t see but that just gives us another reason to head back there again sometime soon hopefully!

    • We actually had a trip to Chicago planned in January and opted against it purely because of the weather. However, we did head to Philly around this same time and experienced snowstorms and freezing cold temperatures but it certainly added to the experience. The walk around downtown Chicago in the Spring sunshine was gorgeous though!

  9. Walking tour is definitely one of the best ways to explore a city, especially if it’s a compact city or one that’s near to ocean/bay. And it throws at us plenty of opportunities to interact with locals, see things around at a slow pace, and most importantly in doing people watching!

  10. I have never visited Chicago but would love to, and when I do I’ll take this walking tour guide along. I would love to see the silver cloud sculpture, I’m sure it would offer great photo opportunities. Great pics by the way!

  11. I’ve been eyeing Chicago lately…too far (for me) for a weekend to drive but I’m keeping a watch on seat sales. looks like such a gorgeous city!

  12. This is a great walking tour by the looks of it. Thanks for sharing. I’m pretty keen to check out Chicago, possibly next year sometime as the finishing point on driving Route 66. I love architecture and Chicago certainly has quite a lot of nice buildings and structures to look at.

    • There is such a nice contrast between old architecture and modern design throughout Chicago! Of course the skyline is one of the more impressive throughout the States so that’s an appealing attraction by itself.

    • Definitely agree with you Brianna that it is a gorgeous city with a vast amount of culture mixed with a nice contrast of modern day design in terms of the architecture. Public transportation is also great in Chicago, the subway/tram system is very good and I have only ever had positive experiences getting around the city.

  13. I lived in Chicago for many years and can assure you that your walking tour takes in many of the great sites. The architectural tour does cost but is certainly one of the best available in the city and provides insight into much of the history…well worth the money.

    • Cheers Tim, I am glad to know that the walking tour we took didn’t leave us missing many of the top attractions in Chicago. I am sure there are many more out there that are worth exploring and that will just be an excuse for us to head back there. We really contemplated doing the architectural tour but opted for our own walking tour instead – I am happy with the decision we made but will likely do that tour on a future visit purely for the experience and to learn more about Chicago’s history!

  14. Some great photos here Chris. Chicago looks like a great city to be able to wander around and one that is full of architecture that I could see Paul snapping away at all day, especially the Cloud Gate Sculpture. Not knowing anything about Chicago, so apologises, is there a story behind that unusual sculpture? Maybe its time to book a flight to the US, we keep reading posts about the country but still haven’t visited! 🙂

    • I am not sure about the specifics behind the Cloud Gate Sculpture but I do know that even before the official name was released, many folks in Chicago referred to this sculpture as ‘The Bean’ predominantly because of its shape. They opted for the ‘official name’ primarily because it represents a gate to the city it reflects. It was designed by London-based artist Anish Kapoor and continues a unique collection of his sculptures around the world.

      I would highly recommend taking a trip over here but make sure that you plan in advance where you want to visit because there is just so much to see and probably nowhere near enough time to see it all!

  15. I have visited this city once on a work trip…I did the walk near Millenium Park. I recall an art gallery of some sort just opposite the Cloud Gate Sculpture…was a really nice time. Also I recall having a meal in the top of the John Hancock Center (I believe)
    This makes me think of documenting a couple of my favourite walks locally…

  16. We also love walking around, it’s good to know that Chicago is a “walkable” city. Your itinerary is great, I’m sure that if we go one day to Chicago, we would use it.

    • We definitely wanted to focus on the downtown neighborhood Roma during this ‘walking tour’ and I agree with you that we did pretty good in seeing as much as we did and covering 4 miles in an afternoon! There are so many opportunities to just stop, take pictures and learn more about Chicago’s history on this route that it’s difficult to keep moving on.

  17. Chicago is just so beautiful. There are just a lot of amazing palces to go to and visit. Yes, I heard a lot of great things about Navy Pier and I sure hope when I come to Chicago, I’ll try having dinner here in their famous restaurant. I’m sure I’ll have a blast with my family. Thanks for sharing Chicago!

    • Thanks April! We always enjoy exploring Chicago and there are still some many aspects of this city we have yet to experience but that just gives us an excuse to head back there again sometime soon hopefully 🙂

    • Cheers Michelle, we really appreciate your kind remarks! Chicago is definitely a walker friendly city and hopefully you will get back there sometime soon to experience the Navy Pier. I am sure that next time we get there (or even yourself), the construction and renovations of the Pier will have finished so I am interested to see how it looks now.


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