Self-Guided Walking Tours to Explore Chicago, Illinois

Follow these 18 expert-designed self-guided walking tours to explore Chicago, Illinois on foot at your own pace. You can also create your own self-guided walk to visit the city attractions which interest you the most.

How it works: download the app "GPSmyCity: Walks in 1K+ Cities" from iTunes App Store or Google Play to your mobile phone or tablet. Each walk comes with a detailed tour map as well as photos and background information for the featured attractions. The app's navigation functions guide you from one attraction to the next. The app works offline, so no data plan is needed when traveling abroad.


Download The GPSmyCity App

Download 'GPSmyCity: Walks in 1K+ Cities' app for IOS   Download 'GPSmyCity: Walks in 1K+ Cities' app for Android
Shopping Tour

Sightseeing Walk: Shopping Tour

Discovering Chinatown

Sightseeing Walk: Discovering Chinatown

The Magnificent Mile Area Walk

Sightseeing Walk: The Magnificent Mile Area Walk

Best Jazz & Blues Clubs Tour

Sightseeing Walk: Best Jazz & Blues Clubs Tour

Nightlife Tour Part 2

Sightseeing Walk: Nightlife Tour Part 2

Art Galleries Tour

Sightseeing Walk: Art Galleries Tour

Souvenir Shopping Part 1

Sightseeing Walk: Souvenir Shopping Part 1

Souvenir Shopping Part 2

Sightseeing Walk: Souvenir Shopping Part 2

Nightlife Tour, Part 1

Sightseeing Walk: Nightlife Tour, Part 1

The Loop Shopping Walk

Discovery Walk: The Loop Shopping Walk

Lincoln Park Walking Tour

Discovery Walk: Lincoln Park Walking Tour

48 Hours in Chicago

Article (B): 48 Hours in Chicago

Adventures in Chicago

Article (B): Adventures in Chicago

Tips for Exploring City on Foot at Your Own Pace

Whether you are in Chicago for a quick stopover or have a few days to see the city in more detail, exploring it on foot, at your own pace, is definitely the way to go. Here are some tips for you to save money, see the best Chicago has to offer, take good care of your feet while walking, and keep your mobile device – your ultimate "work horse" on this trip - well fed and safe.

Saving Money with City Passes


To save yourself time and money visiting Chicago's multiple sights, you may want to resort to the so-called city passes, such as Chicago CityPASS, Go Chicago Card, or Chicago Explorer Pass.

A city pass combines all or multiple Chicago's top highlights, tours and experiences in one prepaid attractions pass, using which you can save incredible amounts on general admission fees as compared to purchasing tickets separately. Often, a city pass also allows you to skip lines at major attractions, thus saving your precious time.

Staying at Walk-Friendly Hotels


Since you're keen on exploring cities on foot (we assume that you are, and this is why you're here), it is important that you stay at a hotel close to the city's major attractions. It saves you time and energy. Here are a few of Chicago hotels conveniently located for a comfortable stroll: The Silversmith Hotel, The Palmer House Hilton, Chicago Athletic Association.

Taking Care of Your Feet


To ensure ultimate satisfaction from a day of walking around the city as big as Chicago, it is imperative to take good care of your feet so as to avoid unpleasant things like blisters, cold or overheated soles, itchy, irritated or otherwise damaged (cracked) skin, etc. Luckily, these days there is no shortage of remedies to address (and, ideally, to prevent) these and other potential problems with feet. Among them: Compression Socks, Rechargeable Battery-Powered Thermo Socks for Cold Weather, Foot Repair Cream, Deodorant Powder, Shoes UV Sterilizer, and many more that you may wish to find a place in your travel kit for.

Travel Gadgets for Your Mobile Device


Your mobile phone or tablet will be your work horse on a self-guided walk. They offer tour map, guide you from one attraction to another, and provide informative background for the sights you wish to visit. Therefore it is absolutely essential to plan against unexpected power outages in the wrong place at the wrong time, much as to ensure the safety of your device.

For these and other contingencies, here's the list of useful appliances: Portable Charger/External Battery Pack, Worldwide Travel Charger Adapter, Power Converter for International Travel Adapter, and Mobile Device Leash.

Exploring City on Guided Tours


We have a strong bias towards exploring a city on foot, at your own pace, because this is how you get to see things up close with a maximum freedom. You decide how much time you wish to spend at each attraction and don't have to worry about following a crowd. That said, however, we also understand that some of you may want to go with a guided tour. If that is your case, here are some guided tours to consider. Be ready to fork out a bit of money, though, as a guided tour of Chicago typically costs somewhere between US$30 and US$70 or more per person:

- Board a hop-on hop-off double-decker (or a bus trolley, in winter) to enjoy sightseeing of Chicago in comfort listening in the headsets either to the recorded commentary in a variety of foreign languages or to a live on-board commentary from a local expert, and be able get on and off at any of the stops along the route as often as you like. The tickets are valid for 24, 48, or 72 hours.

- Dig into the infamous chapter of the history of Chicago, once the criminal capital of the United States, on a crime tour exploring the city’s underworld at its height back in the 1920s-30s. See the actual places and hear the stories associated with the mob names like Al Capone, John Dillinger, and other notorious gangsters.

- Explore the well- and not so well-known pieces of Chicago's design-rich architecture on a 2-hour guided walk to some of the city's prominent landmarks, elegant lobbies, and underground corridors accompanied by educational insights from an expert guide.

- Pedal your way around Chicago on a 4-hour guided bike tour for a chance to get a profound understanding of the city, to taste all of its classical eats in a single go, plus to see the most spectacular highlights of its north side neighborhoods and to cruise one of the most popular waterfront bike paths in the U.S.

- Embark on a self-balancing Segway tour of Chicago – this usually lasts about 1.5-2 hours and allows visitors to get a real sense of the city. Most people (even those aged 70+) find it quite fun and convenient, enabling to cover much more ground than you otherwise could have done by walking.

Day Trips


If you have a full or half day to spare whilst in Chicago, why not use it to explore some of the out-of-town destinations like Oak Park or Plano. For as little as US$55 per person you will get a chance to discover the Frank Lloyd Wright Historic District – the birthplace of the famed Prairie Style architecture, as well as to explore the exterior and interior of the Farnsworth House by Mies van der Rohe and to learn about the life and work of this prominent architect. For any of these tours you will be picked up at a designated place in Chicago and transported by a comfortable air-conditioned vehicle to the destination of your choice and back again.

Useful Travel Guides for Planning Your Trip


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