Discover the Windy City
Getting to Chicago has seldom been easier, with direct flights from London airport to Chicago O’Hare International Airport. Depending on what time your flight arrives, it can be a quick taxi ride into the city – or a long one. The Blue Line subway is an affordable way into Chicago’s core, but the many stops can make it arduous. The train is another option. Take an hour drive to Port Huron, leave your car at the station (no charge), get on the 6:20 a.m. Amtrak train to Chicago and by noonish you are in downtown Chicago. Trains have WiFi and for a small up-charge you can take business class with reclining seats. It’s a great way to get caught up on reading.
Where to stay:
Jill is a big fan of the Kimpton chain of boutique hotels in the U.S. Often located in renovated historical buildings, this chain puts an emphasis on customer service and good food at their hotels.
Hotel Burnham, a National Historic Landmark Building, is a recently renovated main floor brought back a very spacious look with huge windows overlooking State and Washington streets.
Another of Jill’s favourite Kimpton hotels is the award-winning Monaco.
If you are wanting to step back into Chicago’s past, The Drake, at the top of the famous Michigan Avenue “Magnificent Mile” is another worthwhile spot to consider staying.
Where to Eat:
Chicago is a “foodies” haven. The Purple Pig is one of Jill’s “must go” places just off Michigan Ave. Fabulous Mediterranean food and an incredible “buzz”. Be sure to try the sardines and the charred cauliflower.
The Publican restaurant is another of Jill’s favourites. Another hopping Chicago eatery, customers dine at long wooden communal tables. Great selection of beers.
Another Chicago “star” is Rick Bayless’ Frontera Grill. If you can’t get reservations, just patiently wait at the bar and pounce on the first available spot to enjoy some of the best Mexican food you will ever eat.
For exceptional Italian, try Acanto.
If you are looking for a fantastic view and a quieter spot to dine, check out Terzo Piano in the new modern wing at the Art Institute of Chicago for lunch. The modern and spacious restaurant offers great food in a spectacular setting.
Stephani Izard’s The Girl and the Goat continues to be one of Chicago’s “hot spots”. Enjoy innovative small plates. Yes, there’s goat on the menu.
One of Jill’s favourite Italian restaurants is Osteria Via Stato. It’s one of Richard Melman’s establishments and part of Lettuce Entertain You enterprises. Melman operates more than 70 restaurants throughout America with more than 40 of them in Chicago. The range of restaurants is wide, from the tony Tru and Everest to the fun neighbourhood joints like Café Ba-Ba Reeba!.
Spiaggia (the formal side is Barack Obama’s favourite place in Chicago and it’s very “high-end dining”). There is a café side that is much more affordable. Lovely ambiance and view along with decent food (right across from the Drake).
North Pond in Lincoln Park is where you find award-winning chef Bruce Sherman featuring local and organic cuisine. Check out his tasting menu.
Chicago has an Eataly and if you have not visited one yet, it’s an absolute must for all things Italian. There are locations in New York, Rome, Florence, Milan etc. There will be one in Toronto soon.
Spring and summer are ideal for walking and historical tours – Jill recommends the river architectural tour as a “must” – but even in winter, you can experience the richness of this city’s culture by visiting the Shed Aquarium, the Art Institute of Chicago, the Cultural Centre and the Water Tower. Other top-drawer attractions include visiting the John Hancock Centre at sundown, walking through Millennium Park and attending any of the great blues clubs.
Where to Shop:
The Magnificent Mile (Michigan Ave.) is first-rate retail therapy with some of the world’s luxury stores, along with Nike, American Girl, Disney etc.
Looking for some really unique chocolates? A visit to Vosges will introduce you to such exotic items as paprika truffles.
Garrett’s gourmet popcorn is a Chicago legend.
The Hershey Company retail store is always busy and a good stop for the chocolate lover.