Why the Windy City Keeps Winning Awards

Lynn Osmond, President and CEO of Choose Chicago

A lakefront that’s the envy of the world. Amazing architecture. Fabulous food. And Midwestern hospitality.

Those are just some of the reasons that readers of Conde Nast Travel have voted Chicago the best big city in the U.S. six years in a row.

“That means more than 240,000 readers of Conde Nast voted for us,” Lynn Osmond, President and CEO of Choose Chicago, told Open Jaw in a recent interview. “No other city has been chosen number one three years in a row, but we’ve done it six times straight.”

Osmond said the city’s “Midwestern hospitality” is another key factor in Chicago’s favour.

“We’re an American version of a Canadian city,” said Osmond, a native of St. Catharines, Ontario, “And then we have this great food scene and our fabulous river. Every time I host a mayor from Toronto they’re always talking about our lakefront. It’s just a fabulous place.

“We also have the River Walk, which is now complete from Lake Street all the way to Lake Michigan. There’s no charge for the River Walk and gawking at our incredible skyscrapers is a great way to spend an afternoon.”

Osmond said Chicago has 77 neighbourhoods, with immigrants from around the world and distinct cultures.

“Going beyond that and looking at why Canadians should come, we’ll be hosting the first-ever NASCAR street race in North America this summer. It’s on 01 - 02JUL so you can come celebrate Canada day and hear the engines roaring.”

Osmond said the race track is basically a circle with 12 turns and will run just south of the renowned Art Institute of Chicago (one of the top museums in the world, in my opinion).

Image credit: Clayton Hauck Courtesy Choose Chicago

The institute will host a wonderful Salvador Dali exhibit from 18FEB to 12JUN. There’s also great theatre, including the Lyric Opera doing West Side Story, Carmen and Hansel & Gretel. The Joffrey Ballet has Anna Karenina and The Little Mermaid in the upcoming months. If you can’t make it to Chicago, Riccardo Muti and the Chicago Symphony Orchestra will be performing at the Koerner Hall on Bloor Street West in Toronto on 1FEB, 2023.

It’s not slated for completion until 2025, but Osmond said workers have broken ground on the new Obama Center, which is being built in the Jackson Park area of the city, close to the Museum of Science and Industry.

Chicago is home to more than 150 hotels, with prices to suit every budget.

“The new St. Regis is an amazing building designed by female architect Jeanne Gang,” who’s also building One Delisle at Yonge and St. Clair in Toronto. It’s the tallest skyscraper ever built by a female architect, and it will be the 10th tallest building in the U.S.” at 101 stories, and the third tallest in Chicago.

The hotel, which features a wavy exterior and looks to mirror the waves on Lake Michigan, is scheduled to open in March, Osmond said.

Recent hotel openings in Chicago include the citizenM, LaSalle Hotel, and the Sable Hotel at Navy Pier, an attraction all on its own.

Inflation is a major concern of travelers around the world, but Osmond said there are tons of inexpensive and free things to see and do in her city.

“We have a 26 mile lakefront, and you can rent bikes for just a few dollars. We have 23 beaches; we really are a beach town.

“We also have free concerts all summer long in Grant Park,” a lovely park in the heart of downtown Chicago. “Gospel Fest is the last weekend in May. There’s also the Jazz Fest and Blues Fest, and regular concerts in the park, from world music to the Grant Park orchestra?” Of course, there’s also Lollapalooza, which runs 3 - 6AUG.

Osmond also cited neigbourhood festivals, such as the Mole de Mayo festival in Pilsen from 27 - 29MAY for amazing Mexican food, and the Old Town Art Fair 10JUN and 11JUN.

“Almost every weekend there’s a festival that’s free in Chicago,” she said.

One of the activities that’s unique to the city, and one I highly recommend, is the architectural river cruise, which takes you on a boat on the Chicago River and allows you to get up close and personal with some of the most powerful, distinctive architecture in the world. “It’s a wonderful, 90-minute trip with incredible docents who can tell you all about the city.”

A few years ago I also had a fun kayak ride on the river.

Another great activity is a Chicago Greeter Tour, where local residents take you on a tour of their neighbourhood. You’ll learn a lot about the city, and probably get to try some tasty treats along the way.

Chicago is a great sports town, and summer means baseball games at both Wrigley Field (the Cubs) and Guaranteed Rate Field (the White Sox). My wife and I had a terrific, fun tour of Wrigley Field a few years ago. There’s also the Chicago Blackhawks of the NHL, the Chicago Fire (Major League Soccer), the Chicago (WNBA) and the famous Chicago Bulls (NBA), who have former Toronto Raptor DeMar DeRozan on the roster.

“Go to a game and grab a Chicago hot dog and a cold beer,” Osmond suggests.

Chicago is home to 23 restaurants with Michelin stars. Renowned chef Grant Achatz runs Alinea restaurant, which has had three Michelin stars since 2011, Osmond said.

“Michelin also has bib gourmand restaurants that are more affordable, and a lot of places let you bring your own wine,” she added.

In addition to fine dining spots, Chicago is home to famous deep dish pizza, hot beef sandwiches and Chicago hot dogs. Try Portillo’s for a Chicago dog, which has yellow mustard, chopped onions, a dill pickle spear, vivid green relish, tomatoes, pickled peppers and celery salt. Ketchup is not allowed.

And don’t forget Chicago popcorn, a mix of cheese and caramel kernels that’s quite addictive.

Chicago also is home to a great system of parks. The Lincoln Park Zoo is free. There’s also a conservatory at Garfield Park. And don’t forget Millenium Park? Home to the famous, shiny metal art installation formally known as “Cloud Gate,” but usually called “The Bean.”

On top of all that, Chicago is easy to reach for almost every Canadian. The city is only 90 minutes from Toronto. GTA residents can fly Air Canada, United or American Airlines rom Toronto Pearson to Chicago O’Hare Airport. Porter Airlines will take you from the Toronto island Airport to Chicago Midway, which is closer to downtown and far less busy than O’Hare.

“I’m such a fan of those Porter flights” Osmond said.

There also are direct flights to Chicago from Vancouver, Montreal and Calgary.

Jim Byers

Jim Byers is a freelance travel writer based in Toronto. He was formerly travel editor at the Toronto Star and now writes for a variety of publications in Canada and around the world. He's also a regular guest on CBC, CTV News, Global News and other television and radio networks.

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