Not many people would think of Chicago as a holiday destination. Many see it as a stop-off to somewhere else, since it is one end of Route 66 and a major hub for United Airlines.
However, it has a fascinating history — the famous prohibition era of Al Capone, the emergence of its iconic blues music scene, as musicians and immigrants travelled up from New Orleans through the Mississippi Delta.
Oh, and let’s not forget the striking architecture of Frank Lloyd Wright who once said: “Eventually, I think Chicago will be the most beautiful great city left in the world.”
It’s the home of the deep dish pizza and the 22,500 square miles of Lake Michigan, the fifth largest lake in the world, is on the doorstep.
Surely it deserves at least a two-day stay. Follow our guide to what promises to be an interesting short break:
Day 1 -
Kick off your first morning with breakfast at Eggy’s Diner, one of Chicago’s newest eateries near the Fairmont in East Lakeshore Park. There are plenty of vegetarian options.
Take the morning to explore the city: Chicago Architecture River Cruises run by the Chicago Architecture Foundation, will guide you on a 90-minute tour 50 towering skyscrapers on either side of the Chicago River. The Foundation also conducts daily tours of Wright’s home and studio.
Or try a downtown walking tour with a local guide who will take you to many of the city’s hidden gems, such as Marshall Fields’ historic department store, the underground Pedway system and the fascinating Block 37.
Stop for lunch at Lou Malnati. This chain of family owned deep-dish pizza restaurants is an institution in Chicago. Lou Malnati opened in 1971 and his restaurants have used the same recipes and suppliers ever since. They will be the best pizzas you have ever tasted. Period.
Afterwards, explore 350 acres of Millennium Park and Michigan Avenue which runs all the way down one side. At the top end nearest the river, you’ll find Anish Kapoor’s extraordinary “Bean” sculpture or Cloud Gate to give it its proper name.
You’ll also see the 50-foot high Crown Fountains near here, where images of 1000 Chicago citizens blink smile and wink at you then spout out water from their mouths!
As you stroll further down Michigan, you can grab a spot of culture at the Art Institute; it’s the building guarded by two green lion sculptures. Opposite is the beginning of the famous Route 66. There’s a small plaque marking the spot and a little further down is the Blackstone Hotel where Al Capone went twice a week to have his hair styled.
Lastly, just at the far end see the haunting headless and armless Agora Statues, created by Polish Holocaust survivor Magdalena Abakanowicz.
The Field Museum has a huge mix of exhibits from the life of Ghenkis Khan to the history of chocolate, but top billing goes to Sue, the best preserved and most complete T-Rex ever found. She is 67 million years old and over 40 foot long.
Try out a wonderful selection of fish and vegetarian options by master chef Yoshi Katsumura at Yoshi’s Café in Chicago’s Lakeview neighbourhood on Halsted Street. Or enjoy contemporary fish and vegetarian gastro-pub fare at The Gage, just steps from Millennium Park on Michigan Avenue
Cap off a packed day with a taste of the real Chicago blues at Buddy Guy’s Legends blues club, a venue that has been the stage for pretty much every famous blues musician on earth. If you’re lucky, Buddy just might be on the bill.
For quality and choice a Sunday Brunch at 16 on the sixteenth floor of the Trump Hotel will be hard to beat. Thirty-foot high windows give you a great view of Lake Michigan too.
Otherwise, Allium at The Four Seasons; Chef Kevin Hickey pays tribute to some old Chicago classics from his days growing up in Bridgeport neighbourhood including cheese lavosh.
The Chicago History Museum is a must for your second day; the brand new Shalom Chicago exhibition reveals the history of Chicago’s influential Jewish immigrants as seen through the eyes of real family members.
Enjoy a quick lunch at Lincoln Park favourite, RJ Grunt’s, a quirky homage to the ‘60s and ‘70s. Then shop till you drop on Armitage Avenue where notable stores include Lori’s Shoes, Art Effect and Thread Lounge Inc.
Then take a ride on the famous L train or Loop, a raised section of track offering great views of the downtown area. You’ll see a few locations from the Blues Brothers movie too. Then jump on the red line to Clark and Division to Lincoln Park and take a stroll around the free entrance zoo.
For the very best bird’s eye view not just of Chicago, but Illinois, Indiana, Michigan and Wisconsin, The Sky Deck is not to be missed. It takes 60 seconds to rise 1,400 feet up 103 floors of the Willis Tower and then you walk out onto a transparent box jutting out of the building. It really feels like you’re standing in the sky.
The brand new City Winery in Chicago’s trendy West Loop dining district is mix of fine wines, music and culinary arts all under one roof; a fresh approach to dinner theatre. It’s the brainchild of Michael Dorf, founder of The Knitting Factory, one New York’s longest running music venues.
Alternatively, treat yourself to a fine dining experience at chef Anthony Martin’s Tru which offers a $98 fixed price menu featuring an array of mainly fish specialities.
The Second City is an ‘improv’ comedy club and the training ground for Mike Myers, John Belushi, Tina Fey, Steve Carell and Bill Murray.
This is just snapshot of what Chicago has to offer. As Michael Douglas once said: “Hollywood is hype, New York is talk, Chicago just works.”
PACKAGE: America As You Like It has a three-night package from £740 per person, based on two sharing and including return flights on American Airlines from Heathrow to Chicago and three nights room only at the Swissotel Chicago. Subject to availability. Tel: 020 8742 8299