Chicago: An Overview

Chicago, Illinois

Howdy, folks!  It's been a while, hasn't it?  Well, sometimes, real life gets in the way, and in this case, real life = deadlines at my real life architecture job.  But don't worry... the only time-sensitive thing--"Star Wars" Land--is still dirt, concrete, and noodles.  So trust me, you didn't miss much.

The Chicago skyline as viewed from the Willis Tower.

Well, I figured we'd ease back into updates with another #TravelTuesday post, this time finally focusing on a domestic destination after spending five previous trips at various cities on opposite sides of opposite oceans.  In the interest of avoiding coastal bias (or because I happen to have more nice photos of this destination compared to other places), we'll head to the middle of the country and visit Chicago, the Windy City, the White City, the Second City... just a City with a lot of nicknames.


Chicago is served by two main airports: the sprawling O'Hare International Airport (ORD)--which regularly competes with Atlanta's Hartsfield-Jackson International for the title of busiest airport in the world--and the more modest size Midway International Airport (MDW), which is used primarily by Southwest Airlines.  O'Hare is locatest outside and northwest of the city by about 20 miles, while Midway is located southwest and also in the suburbs by about eleven miles.

A comparison of Chicago's two airports in comparison with the heart of the city.

Fortunately, both airports feature convenient access right into the heart of the city via Chicago's light rail service (popularly known as the "L") .  O'Hare is the north terminus of the blue line, which offers an approximately 50 minute train ride (mostly due to the absence of an express line option) into Downtown Chicago.  Midway, on the other hand, is the terminus of the Orange line, which takes about 40 minutes to wind into the city loop (and then completes the loop and heads back out into the airport).

The blue line, running along the I-90 from O'Hare International Airport to Chicago.

Once inside urban Chicago, a rich network of light rail and buses from the Chicago Transit Authority offers a bevvy of options to get around town.  The train is my preferred option, but some destinations definitely will require bus transit.  Fortunately, the CTA offers a variety of passes that work with both, from single use tickets to unlimited-use day and multi-day passes (in 1-, 3-, and 7-day increments.  Visitors will need to purchase a Ventra pass for $5 (which is refunded upon registration of the card) and then load it with credit or the desired pass.  Since I used public transit so often, getting the unlimited-use pass was a no-brainer for me and more than paid for itself.  The 1-day pass is a value after 5 uses; the 3-day pass profiting after about 4 uses a day, and the 7-day pass golden after only 2 uses per day.

A typical CTA light rail stop inside The Loop.

Of course, should you desire, you can also rent a car at the airport and drive around, though you'll have to deal with metropolitan city parking fees and inconveniences--not to mention traffic.


Chicago is a fantastic and historical city that offers a lot of the amenities I love in the international cities I travel.  There really is a great sense of culture and richness throughout, and plenty of things to do!  Those visiting for the first time and interested in "the tourist-y" stuff may also consider purchasing a Chicago CityPass, which offers admission five popular Chicago attractions.


The Chicago skyline is one of the most famous in the world, and the city is rich with noteworthy architecture reflecting styles all across the 20th and 21st century.  This city is home to plenty of Frank Lloyd Wright works and mid-century urban modernism, and it's a treasure trove for any architect or architecture lover.  Some of my favorite buildings and monuments to visit include:
- Willis Tower (formerly the Sears Tower)
- Hancock Tower
- Water Tower and Pumping Station
- Tribune Tower
- Wrigley Building
- Marina City
- Trump Tower
- Aqua Tower
- IBM Building (Mies Van Der Rohe)
- Chicago Board of Trade
- Marshal Fields Building
- Federal Center (Mies Van Der Rohe)
- Marquette Building
- James R. Thompson Center
- Harold Washington Library
- The Rookery (Frank Lloyd Wright)
- Illinois Institute of Technology's S.R. Crown Hall (Mies Van Der Rohe)

The Hancock Tower in the background, behind the historic Water Tower, one of the few structures in the city to survive the 1871 Great Fire.

Bertrand Goldberg's Marina City towers is still used as a residential complex today.

Studio Gang's shapely Aqua residential tower is a relatively recent addition to the Chicago skyline.

- Robie House (Frank Lloyd Wright)
- Isodore Heller House (Frank Lloyd Wright)
- Unity Temple (Frank Lloyd Wright)
- Frank Lloyd Wright Home and Studio
- Oak Park Houses by Frank Lloyd Wright

Frank Lloyd Wright's famous Robie House showcases sleek horizontals and is located south of the city, on the University of Chicago campus.

- Cloud Gate ("The Bean") at Millennium Park
- Buckingham Fountain at Grant Park
- Chicago Architecture Foundation Riverboat Tour

Anish Kapoor's Cloud Gate sculpture has become an icon for the city.

Fans of Married with Children may recognize Buckingham Fountain from the opening credits.

Chicago offers many riverboat architecture tours, but the best one is from the Chicago Architecture Foundation.


Chicago also has some of my favorite museums in the world, covering arts, history, and science.  Many of them are included in the Chicago CityPass too!  Among them are:
- Art Institute of Chicago
- Field Museum
- Adler Planetarium
- Schedd Aquarium
- Museum of Science and Industry
- Chicago's Children Museum
- Museum of Contemporary Art
- Museum of Contemporary Photography
- Terra Museum of Contemporary Art
- Chicago Historical Society

The Art Institute features a plethora of famous works of art, a wonderful Modern Wing by famed architect Renzo Piano, and classical sculptures as well.

The Field Museum is a wonderful natural history museum that is great fun for kids and adults alike.

The Adler Planetarium is great for astronomy buffs and sometimes even offers star gazing programs.

The Museum of Science and Industry is another wonderful learning center to explore, with plenty of hands on exhibits and demonstrations to spark a livelong love of science and moving things.


Naturally, Chicago, being an international city, offers plenty of options in the performing arts, from high theater to low-brow comedy.  On the latter front, the city is famous for multiple comedy and improv troupes, and offers plenty of places for laughs and entertainment:
- Chicago Theater
- Oriental Theater
- American Theater Company
- Chicago Shakespeare Theater
- Civic Opera House
- Symphony Center
- Frank Gehry's Outdoor Music Pavilion at Millennium Park
- Second City
- iO Comedy (ImprovOlympic)

The iconic Chicago Theater is right off an "L" stop.

In Chicago, sporting venues are their own tourist destinations.  Chicago loves its sports, and it has stadiums, ballparks, and arenas ripe with history tied directly with the city.  Sports nuts should be sure to check out:
- Wrigley Field
- U.S. Cellular Field (new Comiskey Park)
- Solider Field
- United Center

Those looking to take a picture with a statue of the Greatest Of All Time can head west to the home of the Chicago Bulls and Blackhawks: the United Center.


Some popular destinations defy the outlines of singular buildings and require a bit more exploration:
- Chinatown
- University of Chicago
- Oak Park Houses by Frank Lloyd Wright

The community of Oak Park, located northwest of Downtown Chicago, features a charming variety of eclectic houses, including many designed by Frank Lloyd Wright.


People might think of churches as destinations in places like Europe, but I have found some beautiful places of worship during my trips to the Windy City as well.  These include:
- Fourth Presbyterian Church
- St. James Episcopal Cathedral
- St. Michael's Church
- Rockefeller Memorial Chapel

Rockefeller Memorial Chapel, at the University of Chicago, is a Gothic Revival style cathedral.


For those looking for outdoor recreation, Chicago has plenty of offerings, especially around the shore of Lake Michigan.  From relaxing parks to zoos to waterside tourist spots, there are definitely a lot of spots to take in entertainment within some setting of nature:
- Grant Park
- Millennium Park
- Jackson Park
- Washington Park
- Lincoln Park Zoo
- Navy Pier
- Michigan Avenue Magnificent Mile
- Brookfield Zoo
- Wicker Park
- Six Flags Great America

Millennium Park is technically a part of Grant Park, but more popular.

Navy Pier offers shopping and simple carnival style entertainment for guests and is more geared to families.

Six Flags Great America, located about an hour north of the city, offers a fantastic line-up of thrill rides and roller coasters.


Chicago is an incredible dining city, and unlike many other places I've visited, I actually have a list of restaurants and establishments that I have targeted in the past and would recommend.  They run all the way from super pricey five star restaurants to inexpensive quick serve joints.  My favorites:
- 25 Degrees
- Alinea
- Avec
- Benny's Chop House
- Black Bird
- Big and Littles
- Calumet Fisheries
- Dragon Lady Lounge
- The Duck Inn
- Francesca's
- Frontera Grill
- The Gage
- Gibsons Bar & Steakhouse
- Goose Island Beer Company
- Graham Elliot Bistro
- Girl and the Goat
- Hagen's Fish Market
- Kuma's Corner
- Lou Malnatti's Pizzeria
- Portillo's
- Purple Pig
- The Terrace at Trump (yes, it's a Trump property, but the views are great)
- Tru
- Weiner Circle
- Urban Belly
- Xoco

Gibsons' Chicago Ribeye is probably the best steak I've ever had.

Kuma' Corner offers a variety of gourmet burgers named after legendary metal bands.  And the burgers also rock.


Given that most of this audience is American, I don't have to really talk about money or customs.  But for anyone coming from abroad, Chicago--like the rest of America--uses the U.S. Dollar.  Cash and credit card are prominently used.  Dining out customarily includes extra payment to tip for service--anywhere from 15-18% or higher, depending on generosity and service offered.


Since I am American, it's hard to really talk much about "communication" and "customs."  But one thing I will say is that my trips to Chicago have always been very pleasant, with the locals reflecting great Midwest hospitality and being generally quite nice to deal with.  I have encountered many kind attitudes and friendly strangers while out and about the city. 

On the other hand, those visiting from out of town should also take care to watch surroundings and travel with guarded attention, as Chicago is a typical American big city with typical big city crime.  Petty theft and pick pockets are not uncommon, and unlike the European and Asian cities I've covered, violent crime is also prevalent--though typically in areas most tourists would avoid.  Still, it's not a bad idea to be watchful, as travelers should do wherever they are.

The sleek, glistening, and flashy Trump Tower looms behind the view created by the classic Wrigley Building.

So that's Chicago's travel post.  It's one of the most popular cities in the U.S. and one of my personal favorites.  Hopefully, this post offers ideas and inspirations to those who may not be familiar with the specifics of the city.  As with all these globe-trekking posts, the intent is to inform and motivation.

Architect. Photographer. Disney nerd. Haunt enthusiast. Travel bugged. Concert fiend. Asian.