The Windy City has been called the world capital of jazz and architecture, and it’s America’s second greatest foodie city, behind only New York. Of course, it’s hard to avoid comparisons with that other skyscraper forest, but we think they’re mostly favorable. Chicago is just that little bit more relaxed, walkable and affordable. It’s also a lot less overwhelming. In fact, do these nine things and you’ll already have covered the highlights.

1.) Catch a Cruise

Chicago is a city of stunning architecture. But if you’re only going to do one design-focused activity, make it the Architecture Foundation Boat Tour. You’ll get the lowdown on all the major skyscrapers, some of the most notable heritage buildings, and a lovely cruise thrown in. Tickets US$46.54 at www.ticketmaster.com. Tours depart from the Chicago’s First Lady Dock, SE corner of Michigan Ave. Bridge.

2.) Get Panned

Chicago is most famous for its deep-dish pizza, served in a pan up to three-inches deep. The crust is thicker, but it also gets baked and deep fried simultaneously at the bottom of the dish. Furthermore, to stop the tomato sauce from making the crust soggy, the cheese is layered onto the dough first, to protect it. The result bears little resemblance to its Italian forefathers but it’s still damn good. Warning: don’t be too greedy, two slices is already a massive feast. We recommend you have it at Lou Malnati’s (6649 N Lincoln, 847-673-0800).

3.) Be Impressed

The Art Institute of Chicago (111 S Michigan Ave. www.artic.edu) showcases antiquities from all four corners of the globe, rotating exhibitions, renaissance masterpieces and more. But where it truly shines is its collection of turn-of-the-century art, most of it painted in France. Some of the best Van Gogh, Renoir and Lautrec paintings are here—making it a lot to take in on one day.

4.) Go to Hell

Chicago isn’t Broadway, but the must-see musical of the moment is currently playing there. On show at the Bank of America Theater until Oct 6, Book of Mormon was created by Trey Parker and Matt Stone, the same guys who made South Park. It’s a hilarious religious satire, with such subtle numbers as “Hasa Diga Eebowai,” which the main characters, religious missionaries in Uganda, soon find out translates to “Fuck You God.” www.ticketmaster.com

5.) Inhale Helium

This happens to be a three-Michelin-star restaurant. But, really, saying Alinea (1723 N. Halsted) does great food doesn’t even begin to describe it. Through deconstruction, Chef Grant Achatz heightens all your senses, turning the 18-course meal (many of which comprise numerous bite-sized treats) into a firework of smells, tastes and textures. One “dish” on our last visit was an edible, helium-filled balloon—yummy and hilarious! They don’t do reservations, here, preferring to sell tables (of four usually) at US$240/person. (At least it means you can get in.) Visit www.facebook.com/alinearestaurant to catch the tables when they go up for sale. 

6.) Jazz it Up

Jazz was invented in Chicago, and it’s still got some of the best (and oldest) bars to prove it. The Jazz Showcase (806 S. Plymouth Ct. 312-360-0234. www.jazzshowcase.com) usually tops the list for attracting top talents and being “the second oldest jazz club in the USA.” If you’d like something with even more of a back story, the Green Mill (4802 N Broadway St., (773) 878-5552. www.greenmilljazz.com) is over 100 years old, and was one of Al Capone’s favorite haunts. It remains one of the best jazz clubs in town, too.

7.) Shop Yankee

Shopping in major cities is becoming a pretty standardized experience. But there are a few fun chain stores in the USA you still can’t get here in Thailand, such as Target and American Apparel. American Apparel (39 S. State St.) is a very fresh, colorful look (we love their t-shirts) and it’s all made in the USA. Target (1 S. State St.) is basically a supermarket and department store, but they occasionally call in big name designers for mini-collections of clothes or furniture. Conveniently, both shops are within a couple minutes’ walk of each other. And the Target store is one of the most gorgeous buildings in the city, thanks to a sumptuous cast iron and terra cotta façade designed by Louis Sullivan in 1899.

8.) Love the Cows

Chicago is famous for its beef. A lot of cattle come up to the Windy City from the Midwest before being sent off to the East Coast. You’ll find plenty of steakhouses in town but our pick would have to be Benny’s Chop House (444 N. Wabash Ave. 312-626-2444). It’s a smidgeon more affordable than some of the more modern-looking places (and we actually like its traditional vibe). It’s also considered one of the best. We concur: the wine list, the steaks and the service are all top-notch. Our pick: a dry-aged New York strip (US$56).

9.) Stay in Style

We’re partial to skyscrapers of the 1920s (you are in Chicago, after all), which also tend to be located in “The Loop” (downtown), meaning you’ll be able to walk to just about everything from your room. We got good deals at the River Hotel (75 E Wacker Drive, www.chicagoriverhotel.com), for under US$200 a night. It was the city’s tallest skyscraper when it was built in 1928, and remains a very handsome building. Another stunning building would have to be the old Carbon Carbide, which its green bronze color and gold accents. It’s now home to a Hard Rock Hotel (230 N Michigan Ave., www.hardrockhotelchicago.com). If you’re really loaded, the most beautiful building in our book is the Reliance Building, now the Burnham Hotel (1 W. Washington St., www.burnhamhotel.com).

ARCHITECTURE ICONS

Tours of Chicago’s Seminal Masterpieces

Chicago is the capital of modern architecture, and was once the home of at least two of 20th century architecture’s biggest names: Mies van der Rohe and Frank Lloyd Wright. If the boat cruise isn’t enough architectonic geekery for you, here are three more tours:

The Farnsworth House

This house by architecture powerhouse Mies van de Rohe continues to define the quintessential modern look. The design is minimal, it’s open to its environment and you can only appreciate how the two interact by paying the place a visit (guided tours only). It’s also really far and impossible to get to by public transportation but car rentals are cheap in the US, so that’s how we recommend you get there. Tour US$20 per person. 14520 River Rd., Plano. 630-552-0052. www.farnsworthhouse.org

The Illinois Institute of Technology, Robbie House and More

Mies van der Rohe’s (him again) architecture faculty building is another huge milestone in modern architecture, providing a massive space without a single column supporting the roof. Conversing with the pure Miesian box, starchitect Rem Koolhaas has created a contemporary deconstructionist response across the street. And the best way to see all this is to hop onto the Architecture Foundation bus tour. Not only does it cover the aforementioned buildings, but it stops in town to visit other major landmarks like The Rookery, an absolute must-see completed by Burnham and Root in 1888. The bus also drops by the Robbie House, Frank Lloyd Wright’s Prairie-style masterpiece. US$45 per person (tour departs from the foundation). 224 South Michigan Ave., 312-922-3432. www.architecture.org

Frank Lloyd Wright Home & Studio

From the outside, Frank Lloyd Wright’s home (viewable by guided tour only) is beautiful, if not quite as impressive as the Robbie House. But the tour also gives you deeper insight into the man, and the interior woodwork is stunning. Conveniently, Wright built many of the houses on his street, which means simply walking down Chicago Avenue, in Oak Park, offers up views of numerous Wright homes. Make sure you also take a look at the nearby Unity Temple (875 Lake St, Oak Park), another of Wright’s masterpieces. Home and studio tour US$15 per person. 951 Chicago Ave., Oak Park. 312-994-4000. www.gowright.org

Essentials

Visa
Thai nationals must apply for a visa at the US Embassy’s Consular Section. Details at bangkok.usembassy.gov
Flights
Several airlines fly from Bangkok to Chicago O’Hare Airport, except there’s no direct flight. The most popular are United (via San Fancisco), Asiana Airlines and Korean Air (via Seoul). A roundtrip ticket is around B50,000.
Currency
US$1 = B29-30