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So, Boston or Chicago for your holiday this year? It’s a tough call, but we’re going to settle this by comparing the accommodation, food, drinks, free things to do and nightlife potential of each city. But first up, ask yourself this: Boston Red Sox or Chicago Cubs? Boston Celtics or Chicago Bulls?

Food

Boston’s famous offerings include:

  • New England clam chowder – go to Cheers (yes, the real life one of the show!)
  • Oysters – at the Union Oyster House
  • Fish and chips – got to be Druid

Chicago’s legendary fare is:

  • Oozing hotdogs – go to The Wiener Circle
  • Fat burgers – try Honky Tonk BBQ
  • Piping hot pizzas – Coalfire is a must

Drinks

The Chicago Cocktail: Brandy, Triple Sec, Bitters and Champagne on the rocks in an Old Fashioned Glass. Shake or stir and serve with lemon.

The Boston Cocktail: Gin, Apricot Brandy, Grenadine Syrup and lemon juice shaken together, then strained into a cocktail glass and served.

Nightlife

Both Boston and Chicago are filled with bars and clubs. Some of the biggest and best nightclubs in Boston include Venu, Tequila Rain and Machine. In Chicago you should try Crescendo, Excalibur or Boutique. In these huge cosmopolitan cities you’re sure to find a bar you love – check out Boylston Street in Boston and Wrigleyville in Chicago.

Free things to do

Savvy thriftsters will love the wealth of fun things to do for free in Chicago and Boston – but which city has the most entertaining free attractions?

Free outdoor concerts: Chicago hosts free festivals such as the Chicago Gospel Music Festival all summer long. And it’s pretty much the same story for Boston – there’s something for every weekend.

Free tours: Chicago has a partnership programme running from The Chicago Greeter Program where they match up willing locals with tour-hungry tourists. In Boston you can tour the Freedom Trail, do a boat tour or just a plain Classic Tour to see the best of the city.

Free museums: Almost every museum in Chicago is free on one day of the week, including the Loyola Museum of Art, the Art Institute of Chicago and the Peggy Notebaert Museum. Boston has the Harvard Museum of Natural History, the Museum of Fine Arts and the Commonwealth Museum – all free on selected days.

Free gardens and parks: Chicago has Jackson Park, the Millennium Park and Lincoln Park. Boston has Boston Common, Blue Hills Reservation and the almighty Emerald Necklace.

More free stuff: The Lincoln Park Zoo in Chicago is free as is the Skokie Northshore Sculpture Park and the Shedd Aquarium. Boston has The Black Heritage Trail, the CharlesTown Navy Yard and the Old North Church.

Accommodation

When it comes to booking a Boston hostel you have plenty of choice and prices start from just €26.71pppn for a shared room or €14.26pppn for a private. There are some top-rated hostels right in the city centre and there’s one near the airport too if you’re not staying for long.

There are more cheap hostels in Chicago and they start at just €17.28pppn in a dorm or €13.75pppn in a private room. Again you can stay right in the centre, or there are also a few motels if you’re road tripping your way around.

So what do you think – Boston or Chicago?

(Images: Featured image – ReneS; clam chowder – Mike Saechang; Bean – Wright Way Photography)

About the author

Oonagh ShielContent Manager at Cheapflights whose travel life can be best summed up as BC (before children) and PC (post children). We only travel during the school holidays so short-haul trips and staycations are our specialities!

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