The Windy City: A weekend trip guide to Chicago

Lifestyle | 27 Apr |

Chicago is perfect for city breaks, but it’s best to plan ahead rather than trying to be entirely spontaneous on your trip.

With that in mind, here are some pieces of advice to ensure that you can make the most out of what the Windy City has to offer.

Get your travel sorted

Getting to Chicago is easy, with great road, air and rail links from all over. Once you’re there, you can also take your pick of different ways to travel the length and breadth of the city.

If you’re on a budget and you want to experience the most authentic transport option, then the L, or elevated train, is your best bet. It runs round the clock on two of the eight lines, and extends way out into the suburbs, as well as catering to the central areas.

If you’ve got a bit more cash to splash, or this is a special vacation for you and your partner, then you could book the best limo service Chicago has to offer, and get chauffeured from A to B instead.

There are also ample taxis, both on road and on the river, so there are lots of routes by which to take in this stunning city.

Book a hotel

Another thing that Chicago is not short of is accommodation, and there are tons of hotels to consider, so once again you can let your budget and tastes guide you.

From high end options like the Peninsula Chicago to chic and boutique upstarts like Ace Hotel, there’s something for everyone. Just be sure to book a room in advance to get the best rates, as leaving it to the last minute might also leave you out of pocket.

Take in some culture

It might be a great place to do business, but Chicago also has a compelling cultural side, so if you want to expand your mind, there’s lots to see and do.

When it comes to museums, there’s the amazing Field Museum with its focus on biology and anthropology, the History Museum with its focus on the movements that forged modern Chicago, the Museum of Contemporary Art with masterpieces from the 1950s onwards, and many more besides.

If you want to see a show in the evenings, there’s the iconic Chicago Theater, the Shakespeare Theater, the Cadillac Palace and a cavalcade of other venues where everything from classic plays to modern musicals can be found.

Grab a bite to eat

The food culture of Chicago is also worth shouting about, and the sheer amount of choice will blow you away, which is appropriate given the city’s nickname!

Not-very-well-kept secrets like Lula Cafe in Logan Square, French-inspired eateries like Dear Margaret in Lake View, cutting edge venues like Esme in Lincoln Park and street food outlets like Rubi’s on the Lower West Side are all available to keep you well fed throughout the day.

Of course if having a Chicago-style pizza is on your bucket list, then booking into places like Spacca Napoli or Giordano’s is a must.

See the sights

Finally, there are a few tourist hotspots that deserve your attention if a trip to Chicago is on the cards.

Cloud Gate in Millennium Park is perhaps the best known of the bunch, but you should also plan to visit the Chicago Observation Deck in the John Hancock Center, as this gives you a bird’s eye view of the entire sprawling metropolis.

Add in a stroll down the Magnificent Mile, and perhaps a visit to Wrigley Field if you’re a baseball fan, and your weekend getaway will be rounded off in style.

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