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The Traveller's Magazine
  •   3 min read

The Windy City never seems to slow down; it is attractive as ever, especially from a local’s eye. Most tourists don’t get past Navy Pier but it looks like most of the city’s real gems lay beyond it. With a couple of tips from insiders, you’ll know where to eat, what to see, when and how in Chicago this summer and on a budget! Discover Chicago like a local, you won’t regret it.

Heading off the beaten path has its advantages: the prices are always cheaper (especially for hotel accommodation), you don’t have to fight at crowds at smaller and less-known museums, you can enjoy things you’ve never seen before, meet people that are actually living in Chicago…

It is really the best way to get a feel for a city if you don’t have a lot of time. The city’s main sights (the Sear’s Towers, the Art Institute of Chicago, shopping along the Mag Mile…) can be seen in a couple of days and after that you should definitely pull a Ferris Bueller and take a day off sightseeing to experience the city for what it is!

What to see and do?

  • City views – Chicago is famed for its tall skyscrapers and dynamic cityscape so why not get a goo look at it from above. Most flock to the Sears Tower Skydeck, which is fine, but if you want a high-up view that is free, head to Cite Restaurant on the 70th floor of Lake Point Tower. It is located across from Navy Pier. The best part: you can get a cocktail and an appetizer for the same price you would have spent on the entrance ticket for the observatory!
    A view from above (img: flickr cc)
  • Pilsen – this is Chicago’s Hispanic neighbourhood which offers a lot to be discovered. It is located in the city’s south side. You’ll also find the University of Chicago nearby and the Museum of Science and Industry.
  • The Neo-Futurists (5153 North Ashland Avenue) – many head to Chicago to see theatre shows and be entertained but it’s not always possible on a budget. The Neo-Futurists have a theatre space above a funeral parlour where they perform 30 plays in 60 minutes… raw and spontaneous. This is your best bet at seeing low cost theatre that is both edgy and extremely entertaining. Admission: $7 plus the sum of a rolled die. The show starts at 23:30.
  • The West Loop – many of the city’s independent and artist-run centres are in this area of town, not to mention Little Italy and University Village.
  • Intuit Museum (756 N. Milwaukee Avenue) – a fresh view of Chicago-based artists that tend to gy awry from the modern trends in contemporary art. This gallery focuses on intuitive and outsider art.

Where to eat and drink?

  • Pizza – there is nothing Chicago is known more for than their deep-dish pizzas. There are more pizza joints in this city than coffee shops so it won’t be hard to find a place with cheap slices.
    Truffles waiting to be claimed at the Swedish Bakery (img: flickr cc)
  • Swedish Bakery (5348 N Clark Street) – pick up a few tasty treats at this traditional bakery: breads, shortbread cookies, pepparkakor ginger thins… Many Swedes immigrated to Chicago in the 19th century, especially to the northern neighbourhoods of the city.
  • Village Tap (2055 West Roscoe Street) – for the best brews in the city head to this place in quaint Roscoe Village. It’s the local hangout and with more than 20 different beers on tap there is certainly one you’ve never tried before. Set at the bar or in the open-air beer garden in the back.
  • BigStar (1531 North Damen) – you won’t fond 2$ tacos anywhere else in the city. This popular place serves hot and delicious Mexican food all day and all night long. If you have to wait to be seated, don’t sweat it. The food is worth it.

Have you ever been to America’s Windy City? Have any tips for must-see places? Where did you find the best Chicago-style pizzas? Chicago is one of the country’s largest and busiest airport hubs which makes it easy to find cheap flights to Chicago.

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