Being home to the busiest airport in the world, O’Hare International, Chicago is often a lay-over point for many travellers heading further west.  But being the third largest city in the U.S. with a rich cultural history that quickly diffused into popular American culture, you’ll want to get the dish on Chicago (deep-dish that is). To get the most out of this sprawling city with the least effort, choose to stay Downton, in the Loop or in the Grant Park area and invest in a CTA 3 day visitor pass that will give you unlimited public transport for around $20.

Day One:

The Loop –

Start your trip by getting to know the city you’re in. On Saturday mornings there is a free Loop Tour train which gives you a guided tour of the city within the Loop area (the Loop is an elevated train that circles approx. an 8 block by 5 block radius of Downtown Chicago). Get your free tickets from the Cultural Centre, which is a building worth seeing in itself, straight across from Grant Park on East Washington Street.

The Taste-

If you’re lucky enough to travel to Chicago in mid-July, you’ll be able to take part in the world’s biggest food festival: The Taste. Held in Grant Park the festival offers a massive array of food but also live performances.

Museum Campus –

If you Head south from Grant Park you’ll find yourself near Museum Campus, a lakefront park that encompasses three museums within it’s limits. My pick is the Adler Planetarium & Astronomy Museum. Exhibitions include a chance to learn about the history of astronomy, our own solar system and the ‘Hidden Wonders’ of our night sky. Awe inspiring for kids and adults, general admission is $12 for adults and $8 for children.

 Navy Pier –

From Museum Campus, take the water taxi up to Navy Pier. At around $8 for adults, it’s a great way to see the city from a different vantage point and is often quicker than sitting in Chicago traffic.

Navy Pier itself is just east of Streeterville and stretches out almost a kilometre from the shore. Offering shopping, restaurants and museums, it makes for a leisurely evening but the highlight is the 150ft Ferris wheel. Wait for the sun to begin to set and for the twinkling pier lights to come on, then take a ride where the first ever Ferris wheel was constructed.

Day Two:

Retail therapy on the Magnificent Mile –

If you’re looking for a bit of luxury, head to The Magnificent Mile (North Michigan Ave) just west of Streeterville in the Near North Side neighbourhood. With nearly 500 upscale stores and boutiques, this avenue of 13 blocks is a large dose of retail therapy. Be sure to take a quick tour of the Water Tower, built in 1869 and one of the few structures to survive the Great Chicago Fire in 1871 – a beautifully unexpected piece of history on this commercial strip.

Wrigley Field & the Batting Cages-

Travel north from the Magnificent Mile to Lakeview.

Chicago is well known for its dedication to hosting sporting events and if you’re a baseball fan, watching a Cubs game at the Wrigley Field stadium– named after the infamous chewing gum mogul – is a must. Wrigley Field is located in the northern part of the Lakeview Neighbourhood and the stadium and it’s surrounding area are often referred to as Wrigleyville. For hard-core Cubs fans, head to the Cubby Bear bar across the street from the stadium on West Addison Street. If you’re looking for a piece of the baseball action yourself, Slugger’s is the place for you, on north Clark Street, with their batting cages upstairs.

 The Willis Tower –

Head back to the Loop, and make your way to The Willis Tower on South Wacker Drive. The tallest building in North America has to offer some pretty good views right? Willis Tower is fully prepared to take advantage of those views. The Skydeck is located on the 103rd floor of the Willis Tower and offers views that can sometimes span as far as four states. Four! For the daredevils out there, edge out onto the glass balconies that offer a view of the vertical drop, 1350ft straight down. For those who suffer from vertigo, keep your feet firmly on the non-glass floor and just take in the cityscape and the views of the Great lakes.

Extra Options –

Chicago has a vast history of working class ethnic migration and many neighbourhoods have retained their authentic roots. For the best cuisine Chicago has to offer, head to your favourite spot:

Mexican neighbourhoods can be found on Pilsen, 18th street and La Villita, 26th street. For Puerto Rican cuisine, head to Paseo Boricua in the Humboldt Park area. Greektown can be found on South Halsted Street. Little Italy, for that infamous deep-dish pizza-pie, can be found on Taylor street. Chinatown is located in Armour Square. The Polish neighbourhood of West Town will likely have the best Chicago-style hot dogs, using polish sausage and toppings galore. 

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