or the “Windy City” or Chi-town as it’s more lovingly referred to (or the Second City less so) is a destination in it’s own right. Off the bat - I just suggest you make it a spring, summer or early fall trip (come in middle of winter and pack on the layers - BRRR). Other than it’s deep winter freeze, Chicago is primarily known for it’s architecture, it’s theatre, music scene and the easygoing mid westerners that live here (that take pride in not being like New York). Also, being the 3rd largest city in the US and one of it’s most multicultural and it is one that loves to eat. and eat. and eat some more. I did a LOT of eating here (and walking everywhere afterwards). There are so many restaurants that you will never hit them all, rounding down this list from my friends suggestions was hard, just make sure to enjoy at least 1 deep dish pizza and some of the steak Chicago is famous for.
Chicago is a fun town that is more than slightly reminiscent of Toronto, but with skyscrapers this big and steaks this juicy it can only be American.
MY CHICAGO LIST
Porter Airlines flies into Midway Airport (located closer to downtown) from Toronto Island Airport. https://www.flyporter.com/
other than that, every major US and European/Asian airline flies in.
Acme Hotel Co: http://www.acmehotelcompany.com/ the Chicago version of the Ace, if you will…
James Hotel: http://www.jameshotels.com/Chicago.aspx the original and still (imho) best “design” hotel in town. Spacious rooms, great service and home to one of the best steakhouses in town: http://davidburkesprimehouse.com/
Lincoln: http://www.jdvhotels.com/hotels/chicago/lincoln a new hotel that, as per it’s name, is situated next to Lincoln Park.
Longman & Eagle: http://www.longmanandeagle.com/ a trendy restaurant with some designer rooms, book early.
Public: http://www.publichotels.com/chicago/home/ Ian Schrager x Marriott have created this place. Of course it’s the hottest thing (right now).
Andy’s Thai Kitchen: http://chicago.menupages.com/restaurants/andys-thai-kitchen/ supposedly the best Thai resto in town.
Au Cheval: http://aucheval.tumblr.com/ comfort food updated.
Balena: http://balenachicago.com/ very highly regarded.
Baume & Brix: http://baumeandbrix.com/ funky.
Bellyshack: http://www.bellyshack.com/ Korean/Puerto Rican fusion. Yeah you heard right.
Big Shoulders Coffee: http://bigshoulderscoffee.com/ nice big airy space for some good coffee.
Big Star: http://www.bigstarchicago.com/ Mexican hipster.
Caffe Streets: http://caffestreets.com/ love the design. Coffee is not bad either…
Do-Rite Donuts: http://doritedonuts.com/ deep fried heaven.
Girl and the Goat: http://www.girlandthegoat.com/ crazy popular so make sure to book!
Handlebar: http://www.handlebarchicago.com/ vegetarian resto/bar.
Jam: http://jamrestaurant.com/ “world famous” brunch HERE!
Kickstand Espresso Bar: http://kickstandcoffee.com/
Lou Malnati’s: http://www.loumalnatis.com/ locals can get into fistfights over their choice of best Chicago Deep Dish pizza, and I’m sure they all have merits however Lou’s was my personal favourite. no punches ok?
Lula Cafe: http://www.lulacafe.com/ a local institution where all of Chicago goes for brunch so go early.
Mana Food Bar: http://www.manafoodbar.com/ vegetarian cuisine.
Maude’s Liquor Bar: http://www.maudesliquorbar.com/ dark, sexy and french.
Mercat a la Planxa: http://mercatchicago.com/ catalan tapas.
Mindy’s Hot Chocolate: http://www.hotchocolatechicago.com/ skip the food and go straight for dessert.
Next: https://www.nextrestaurant.com/ you have to buy tickets in advance but just do it…
Publican: http://thepublicanrestaurant.com/ meat and beer.
Ruxbin: http://www.ruxbinchicago.com/site/ a cozy neighbourhood place everyone loves.
The Savoy: http://savoychicago.com/chi/ Go here for some top flight seafood when the meat gets to be too much.
Schwa: http://schwarestaurant.com/ informal, seasonal, locals love this place.
La Sirena Clandestina: http://www.lasirenachicago.com/ dark and sexy.
Starlounge Coffee Bar: http://www.starloungecoffee.com/ the retail “front” of Dark Matters roasting co.
Green Mill Jazz: http://www.greenmilljazz.com/
Art Institute: http://www.artic.edu/
Chicago Architecture Foundation: http://www.architecture.org/tours runs all kinds of tours that highlight all the architecture Chicago is famous for. I recommend the walking tours (esp. the Modern Skyscrapers (1950s-Present) one). The boat ones are fun too.
Haberdash: http://haberdashmen.com/ 2 locations of menswear.
Heritage Bikes: http://www.heritagebicycles.com/ cool bike shop (and cafe).
Milennium Park: http://www.cityofchicago.org/city/en/depts/dca/supp_info/millennium_park.html you already know about this one right?
Museum of Contemporary Art Chicago: http://www.mcachicago.org/
Public Works: http://www.thispublicworks.com/about/ small private art gallery.
RSVP Gallery: http://rsvpgallery.com/index.php not a gallery, actually a shop with street wear.
Saint Alfred: http://www.stalfred.com/home/ for cool labels.
Siskel Film Center: http://www.siskelfilmcenter.org/ when it’s too cold to be outside.
Skydeck: http://www.theskydeck.com/the-tower/facts-about-the-ledge where better to get a view of Chicago’s famous architecture? Located in the Willis Tower (or still better known by it’s previous name - the Sears Tower).
A FEW TIPS
as mentioned above, and it bears repeating - DO NOT visit in Winter. The lake blows all sorts of freezing nasty into the city. And your flight is likely to be delayed as well. ***This means use my guide now, or wait until next Spring.***
CTA: http://www.transitchicago.com/ is the local transit authority. The single fare per ride starts at $2.25. The mixed subway/elevated train lines (called the “EL” by the locals) goes as far both O’Hare and Midway airports. BONUS POINTS!
be ready to eat MEAT. Chicago is a meat lovers town and they love to show it.
http://deepspacesorg.tumblr.com/ is a Chicago based photographers cool blog.
image via sippinggrapesoda, mixedmani, we love food*