5 Favorite Spots From An Expat In Chicago

Chicago is a beautiful and vibrant city, defined by its towering skyscrapers, gorgeous architecture and bustling vibe. After close to one year of living in Chicago, I have slowly gotten accustomed to life there and even start to have my own favorite spots. Now that I am back to my home country Singapore for a vacation, I can’t help thinking longingly about my idyllic life in Chicago at times. This post is dedicated to the beautiful sites of the Windy City and transportation tips on how to get there.

The University of Chicago


The University of Chicago is without a doubt the most beautiful place in Chicago in my eyes. With the English Gothic style of architecture and  ivy-covered walls, the U.of C. fulfils my imagination of what an old university steeped in history should look like. Away from the hustle and bustle of the downtown city, this Hogwarts-like campus is a place I will be happy to get lost in.

When you are there, be sure to check out the majestic Rockefeller Memorial Chapel, the gorgeous Harper Memorial library, the slightly futuristic looking Joe and Rika Mansueto library that allows you to read with natural sunlight streaming through the glass dome and the charming 57th Street bookstore.

How to get there via public transport:

You can board the Metra train at the Millennium Park, Van Buren Street, or Museum Campus stations to ride down to campus. Disembark at the 55/56/57th Street or 59th Street Stations, then turn right to walk west to campus. However you will need to check its schedule online as the train departs at specific times. The fare is about $3.00.

The Magnificent Mile


Home to shops, shops and more shops, The Magnificent Mile shopping belt is a must-go for all serious shopaholics. I like that the shopping belt is one long straight strip which makes it very easy to navigate without getting lost. Also, contrary to popular belief that it is only suited for upscale shopping, I can get my bargain hauls of branded goods from TJ Maxx., Marshalls and Nordstrom Rack  at a huge fraction of its original price. Definitely a good place to shop even for someone on a budget like me.

How to get there via public transport:

Check out the various ways here.

The Art Institute Of Chicago


As a member of the Art Institute of Chicago, I spend many afternoons wandering aimlessly around the huge museum looking at art pieces and sculptures before stopping by at the member’s cafe for a free drink. I am no high-brow art connoisseur and often could not quite tell the difference between an art work by a famous artist and a not-so-famous artist (in fact I even once criticized a painting for being very ugly before realizing that is is Van Gogh’s), but I like surrounding myself with beautiful objects and this art museum certainly has no lack of beautiful paintings. Quiet and spacious, with no end of paintings and sculptures to see, visiting the Art Institute of Chicago has a calming effect on me.

How to get there via public transport:

The Art Institute is easily accessible via the city’s “L” train system. You can board the “L” train and get off at Adams/Wabash stop and walk there. The cost of one “L” ride is $2.25.

More details here

South Garden


Just a short walk away from the famous and way-more-crowded Millennium Park, the Art Institute’s South Garden is a welcome respite if you feel like surrounding yourself with lush greenery but without the people. I adore this small, well-maintained garden with short trees that offer a low canopy of shade. Designed by modern landscape architect Dan Kiley, this beautiful South Garden is soothing to the senses, which explains why I often see individuals simply sitting there to read or even to catch a nap under the trees.

How to get there:

It is just on the south side of  the Art Institute. 

Chicago Lakefront Trail


The lakefront trail is so incredible! I can’t believe it took me so long to discover this 18-mile-long paved path that extends from the North Side to the South Side with Lake Michigan on one side and greenery on the other side. I veered off the Chicago Riverwalk recently and passed by the peaceful Dusable Harbor and Monroe Harbor that boast impressive views of sparkling waters, yachts and the ferris wheel at Navy Pier. Running along this lakefront trail with such fantastic views and ducks waddling about on the grass patches beside me is truly invigorating to the senses.

How to get there:

It is a long stretch but if you want to walk past Dusable Harbor and Monroe Harbor, just walk a short distance from the Chicago Riverwalk.