Luxury holidays in Chicago

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When to go

The winter months of December to February are tourist-deterringly chilly, so if you can face the cold and just want to bounce from cosy bar to restaurant, make the most of the quiet. In summer (around July and August), the temperature is more cooperative, allowing for trips to the beach, breezy bike rides and sunshine strolls around the city. Unless you can really hold your Guinness, get out of Dodge on 17 March, when the St Patrick’s Day Parade snakes drunkenly through the city.

Getting there

  • Planes

    Catch a direct flight from New York City to Chicago O’Hare International Airport (ORD) or Chicago Midway Airport (MDW) on most commercial domestic and international carriers such as Southwest, United or American Airlines. Both airports are about 25 minutes by car from downtown Chicago. You can take the Blue Line subway from O’Hare or the Orange Line from Midway into downtown.
  • Trains

    Chicago Union Station, on the corner Canal and Jackson streets, has Amtrak service which includes routes to and from Los Angeles, Seattle and New Orleans.
  • Automobiles

    You can easily hire a car from the airport but it’s not necessary; with the daily bumper to bumper traffic it’s much easier to get around by taxi.
  • Taxis

    You can easily flag metered taxis on the street; ask if they accept credit cards as not all do. You can hire a limo or car through Metropolitan Limousine (+1 800 437 1700 ;