She is always a novelty; for she is never the Chicago you saw when you passed through the last time
— Mark Twain —

Traveling to Chicago

By plane

There are two airports located in the city of Chicago, the Chicago O’Hare International Airport as well as the Midway International Airport. Another option is the Gary International Airport in the southern suburbs and already within the state of Indiana. Within the western suburbs of Chicago, you will find the DuPage (domestic) Airport. Neither of the airports is too far away from the business center of Chicago, the Chicago city rail system connects to both to the Midway (orange line) and O’Hare airport (blue line).

By (long-distance) bus

I arrived in Chicago on a long-distance bus journey from Washington, D.C., taking 20 hours. There are different bus providers available, the greyhound lines bus service has an extensive network, especially in the northern States. Moreover, it provides specific services to customers with disabilities. Coming from Washington, D.C., we had stopovers in Pittsburgh (Pennsylvania) and Cleveland (Ohio). I provide more and additional information on traveling by long-distance bus within my article on the road trip in the North-Eastern States.


There are plenty of recommendations available for one to multi-day trips from Chicago by car. I have found some interesting tips on the blog the Local Tourist. If you want to explore not only the city of Chicago but also the surrounding area, you might either drive to Chicago or rent a car for some days. However, the traffic within Chicago is heavy and on-street parking is nearly impossible to find. Since Chicago’s network of public transport is quite extensive and accessible, you will not need a car within the city. I’d recommend checking for (included) parking spots at your hotel. Most of Chicago’s streets have metered parking, parking garages are rather expensive.

Staying in Chicago

Public transport

The public transport provider of Chicago is the Chicago Transit Authority (CTA). The latter even offers unlimited-ride passes for multiple days, in my opinion a very cost-effective way to travel around the city. Moreover, the CTA’s information on accessibility outlines the space provided for wheelchair users within every CTA train. However, if you require a gap filler to get on a train, you are requested to ask the customer assistant or train operator for assistance. Depending on your station, customer assistants might not always be at the spot and would need to be called.

Hotel recommendation

During my trip around the North-Eastern States, my friend and I stayed in the Chicago Getaway Hostel. Honestly, I didn’t even recognize the building as a hostel from the street. As soon as I entered, I encountered plenty of space in common areas and a well-equipped kitchen. The bedroom was clean and well maintained. However, this hostel is not accessible by wheelchair, since there are some stairs to reach the front door. TripAdvisor offers the filter upon accessibility of wheelchairs, there are both hostels and hotels available.

Places to eat out

There are plenty of restaurants located in Downtown Chicago, even international food chains. My favorite place was “Panda Express”, an affordable Chinese inspired American restaurant. Since there are so many businesses located within Downtown Chicago, you will find the more expensive restaurants within this area. If you are looking for good quality for less money, I recommend to leave Downtown Chicago and check out the other quarters.

During daytime, Downtown Chicago is really busy. However, during nighttime, the business quarter is literally dead. All nightlife happens in the surrounding quarters, where people actually live. If you are looking for nice bars and pubs for your evenings and nights, leave Downtown Chicago. Moreover, if you stick to a place close to the lakeside, you might even be able to enjoy a great view on the skyscrapers during dawn and night.

Exploring Chicago

Lake Michigan and connecting Parks

The city of Chicago is one of the biggest cities of the States and located at the southwestern tip of Lake Michigan. Chicago belongs to the state of Illinois, its suburbs even reach into Indiana and Wisconsin following the coastline of Lake Michigan. Therefore, the coastline offers plenty of things to do. Many of Chicago’s parks are at the shoreline, providing great opportunities for relaxed strolling.

Downtown Chicago

The streets of Downtown Chicago follow a regular grid pattern. The outer quarters keep the streets in parallel, though, in less regular grids. Downtown Chicago, containing the major business skyscrapers, got the nickname “the Loop”. Within this area, you will find plenty of restaurants, shops, theaters, and parks. During daytime, this district is very busy, whereas during nighttime there is literally nothing happening. Those fancy business buildings don’t connect directly to Lake Michigan, there are some nice and famous parks in between. Concretely, these are the Millennium Park and the Grant Park.

The most well-known architecture of Chicago might be “the bean” within Millennium Park. Actually, the huge and bean-shaped sculpture is (officially) called Cloud Gate. The bean is easily accessible on a wheelchair. Respective ramps are available from the side facing the lake. Also within the Millennium Park and very close to the bean, you will find the Jay Pritzker Pavilion. Especially during summer, concerts, or shows take place within this band shell pavilion.

Next to the Millennium Park, you will find the Grant Park. This park extends across the whole coastline of Downtown Chicago and is separated from the shore by a busy street. The Buckingham Fountain is a very famous and central spot within the entire park, offering great views from the Downtown skyscrapers. South of the Grant Park (leaving the Loop), you will find the Field Museum of Natural History, its northern boundary consists of the Millennium Park including the Maggie Daley Park area.

Parks beyond the Loop

Any parks beyond the Loop provide space for sports or other (relaxing) activities of locals. Moreover, there are a variety of beaches to actually swim in the lake. Of course, there are different types of water sports available, depending on the season and temperatures. If you plan to check out the Museum of Science and Industry, you can combine this with a visit to Jackson Park. There are multiple parks in any quarters, however, the suburbs are much greener than the city of Chicago itself. Based on my own travel experience, I would like to highlight Lincoln Park, in which you find the free Lincoln Park Zoo.

Art and Architecture

If you only walk along the streets, the skyscrapers might just be skyscrapers. Therefore, my friend and I did a city walking tour called “Modern Skyscrapers (1950 – present)” from the Chicago Architecture Foundation. During the tour, we focused on skyscrapers of modern times, which are mostly composed of steel and fit to their context and environment. By contrast, postmodern skyscrapers are completely neutral, they are built to fit anyplace on earth. The epoch following postmodernism would have buildings similar to postmodern skyscrapers, which – as the contrast – would fit into their environment again.

Many of the postmodern skyscraper obtain thick glass windows which are completely mirrored. The advantage for the inner rooms is the unnecessity of any air conditioning. From the outside, the mirrors work in a way to lighten up the streets, reflecting the bright daylight downwards. Due to the many reflecting skyscrapers, it is even brighter along the streets in the Loop compared to other quarters. I would like to recommend checking out the Marshall Field and company building, as well as the Frank Lloyd Wright home and studio. Wright designed different cool art nouveau buildings across the city. If you want to dive deeper into art, the Art Institute of Chicago is a good recommendation.


Three further recommendations to check out

I definitely recommend strolling along the streets next to the Chicago River. There are skyscrapers next to beautiful bridges in a busy and vivid atmosphere. The river has a bright blue color if the blue sky reflects down from the sky through the skyscrapers, offering great photo-spots. If along the Chicago River or along any other busy streets, there are plenty of markets selling both high quality food, souvenirs, and other crafts.

The Sears Tower (or “Willis Tower”) has a Sky Deck, offering an amazing view over the city line from the bird-eye’s perspective. If you check out the sunset time of the day and buy your ticket accordingly, you may enjoy the view both during daytime, dawn, and nighttime. While you recognize the huge area of differently shaped skyscrapers and houses during daytime, you might be impressed by the miles of lighted streets converging to infinity.

Within the North-west direction of the Loop, you can visit the old town, the former German quarter. You know that you are at the right spot if you check for the street names. Within this quarter, there is the St Michael Catholic Church, the only church surviving the great fire of Chicago (8.-10.10. 1871).

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