Best Of Chicago: The Windy City

Best Of Chicago: The Windy City
‘Chicagoland’, ‘The Third Coast’ or ‘The Windy City’: it’s not difficult to work out what makes Chicago the 3rd most populous city in the US. Famed for the towering architecture that graces its turquoise lakes, palm-width pizza slices and the birthplace of House music. Here are some recommendations for a long weekend.


City Sights

After the 19th century fire that destroyed most of the city, the streets were rebuilt from the original townsite plat in a grid formation. I found that this makes it extremely easy to get around by foot, as all the roads are so straight. Nevertheless should your skills of navigation fail you, Lyft App seems to be more popular than Uber.




  1. Millennium Park : where you’ll find the iconic silver ‘Bean’ of Chicago (sculptor Anish Kapoor’s 110-ton Cloud Gate). Catch a concert at The Pavilion or simply picnic in 25 acres of greenery and sunshine.
  2. The Field Museum : Chicago’s answer to London’s Natural History Museum. I caught the seasonal Tattoo exhibition and felt inspired by some Tibetan designs, watched a 4D feature on China’s Terracotta army and learned a lesson in cannibalism in the ‘Pacific Spirits’ gallery. Admission was about 30-40 dollars for an all-access pass.
  3. The Second City : Improvised comedy and the launch pad for current stars such as Bill Murray and Tina Fey.
  4. Museum Of Contemporary Art : One of the largest collections in the nation and also a host of regular film screenings and performances.
  5. Lincoln Park Zoo : Now featuring ‘The Regenstein Macaque Forest’, where snow monkeys ironically enjoy a relaxing hot tub.
  6. Adler Planetarium : Take a virtual reality trip through space and time.
  7. Navy Pier : akin to London’s South Bank. Ferris wheels, IMAX, mini golf, plenty of family activities and beautiful sandy sunsets.
  8. SoFarSounds : A company supporting up and coming local talent, discover new sounds whilst enjoying beer on tap or BYOB.
  9. Architecture Tour : there’s no better way to appreciate Chicago’s skylines than via river boat tour – complete with Bloody Mary’s, Spiked Bailey’s cocoa and narrated by witty volunteers. Grab your camera, wrap up warm and soak up the history and character of this gorgeous city.


Refuelling Stations

  1. Roisters : the child of culinary mad scientist, Grant Achatz and part of the famous Alinea Group restaurants. Best known for being a leader of molecular gastronomy, that temporarily lost his sense of taste and still managed to become one of the most recognised chefs in the world. The first time I’ve tried chocolate marshmallow foie gras and I highly recommend it
  2. Lou’s pizza : this chain is only to be found in Chicago. Taste the classic Deep Dish – what can only be described as more like cake, than a pizza, in a good way. Wash down with ‘deep dish bloody mary’s’, served with cocktail skewers of meat and cheese.
  3. China Town : well priced Dim Sum, Boba Tea and SE Asian trinkets
  4. The Tavern : best for brunch time Bloody Marys (yes this was a recurrent theme during my time here)
  5. FarmHouse Chicago : Farm-themed hangout serving all-american comfort foods
  6. Mindy’s Hot Chocolate : best for rich desserts and winter warmers
  7. Gene & Georgetti : old school steak house serving everything chicago does best – meat, seafood and carby specialties.
  8. Chicago’s Home of Chicken and Waffles : exactly what it says on the tin, including all the other weird things Americans like to eat, such as biscuits in gravy (translation – a scone in bread sauce).




Watering Holes

  1. London House : I felt as though this riverside balcony was calling my name. Enjoy custom made cocktails whilst bathing in the glow of the reflective surroundings at dusk.
  2. The Winery : use the footpaths or take a water taxi to this venue, located along the scenic River Walk. Enjoy wine served in science beakers and feel truly engulfed by the impressive architecture.
  3. The Terrace at Trump : might as well make the most of the only redeeming feature this building has, skyline views and cocktails from a hotel rooftop
  4. Green Mill Cocktail Lounge : Home to Al Capone and other gangsters in the 1920s, pop by on a Saturday afternoon for a taste of some of the city’s best jazz music.





1 Comment

  1. May 2017 / 3:43 pm

    Chicago is one of my favourite US cities, but I haven’t been there for quite a few years. Will have to fix that. Thanks for your interest in my travel blog.