As the closest sister city to Toronto (and the only one in America), Chicago is constantly ranked as one of the top tourist destinations in the U.S., and for very good reason. With an abundance of attractions and events, along with great food, an amazing waterfront and beautiful architecture, it’s worth the roughly eight-hour drive from Ontario to visit the Windy City this summer.
“There’s so much going on in the city of Chicago,” says Lynn Osmond, president and CEO of Choose Chicago. “Lots of festivals, music, food, sports.… We just have so much to share as a city.”
Chicago is just over an eight-hour drive from the Toronto area. Heading west on Highway 401, you’ll cross the border into Detroit from Windsor, Ont. A majority of the drive after that is through Michigan before you cross into Indiana and gain an hour before finally entering Illinois. If you want to take a break along the drive, Ann Arbor or Kalamazoo, Mich., are both excellent cities to stop in.
Where to stay
To be close to all the main attractions and sight-seeing ventures, as well as near great restaurants, bars and shopping, staying in the area known as The Loop is your best option. This area covers the heart of downtown Chicago and includes Millennium Park, Willis Tower, the theatre district, the Chicago Riverwalk and so much more.
Hotels are not cheap in Chicago, but some of the more budget-friendly ones can be found on W or E Monroe Street. These include the Hampton Inn Majestic, located right next to the CIBC Theatre, the Hyatt Centric The Loop a little farther west and Palmer House (a Hilton Hotel), which is more east and closer to Millennium Park. From these hotels you’re able to walk to most of the big attractions, including Millennium Park, Willis Tower, the Magnificent Mile and the Riverwalk. You’re also close to many amenities as well as the Chicago Transit “L” train.
What to do
In a city with so many options, narrowing down what to do in Chicago is no easy task. Here are our top must-do picks.
Architecture river cruise
One of the first things you’ll notice about Chicago is the amazing architecture throughout the city, and if you want to learn more about these unique structures, the Chicago Architecture River Cruise is the most exciting way.
“The architecture river cruise is just a great way to get an overview of the city and take you through the city,” Osmond says.
Located near the Riverwalk, the 90-minute cruise runs daily with daytime and evening departures. You’ll get great views of all the unique buildings Chicago has to offer while a tour guide explains and educates about each one. With a bar onboard, you can also enjoy a drink or two on the cruise and there are washrooms available.
Tickets cost US$51.96 plus tax for a daytime ride and US$55.74 plus tax for an evening cruise. For an extra US$5 you can access the Chicago Architecture Center.
The third-largest building in the Western Hemisphere, the Willis Tower gives you unobstructed views of the entire city from its 360-degree Skydeck, which also includes The Ledge — glass boxes you can stand in that stick out 4.3 feet from the building, 1,353 feet in the air. The building itself (the former Sears Tower) is stunning and also features a food court in the lobby with a Shake Shack.
The Willis Tower is open from 9 a.m. to 10 p.m. Monday to Friday and 8:30 a.m. to 10 p.m. Saturday and Sunday until September (hours are shortened from October to February). Tickets cost US$38.50 for those 12-plus and US$30.50 for children three to 11. Tickets must be purchased in advance as they are for timed entry.
Along with the iconic Cloud Gate (a giant metallic sculpture also known as “The Bean”), Millennium Park is home to Crown Fountain (which features two giant 50-foot glass video screens with faces on them), and the award-winning Lurie Garden. There are also regular events held in the park, including a free summer music series. Visitors can spend hours here without getting bored or spending any money.
One of the biggest tourist stops, Navy Pier has something to offer everyone. Take in a view of the city from atop the giant Centennial Wheel, enjoy a famous Chicago-style deep dish pizza at Giordano’s or stop for a drink at the Navy Pier Beer Garden. This is also one of the best spots to grab some souvenirs and you must pop into Garrett’s for a bag of Chicago Mix popcorn before you leave. If you just want to take it easy you can walk to the end of the pier for a beautiful photo op of Lake Michigan.
Osmond says the West Loop, which is the old meat-packing district of Chicago, is a hidden gem that is only now just starting to get on people’s radar.
“It’s home to some of the best restaurants and has got a real hip flavour to it. Cool boutiques, great rooftops where you can have drinks and see the world, and also some great hidden alley bars you can discover. Just some really cool things to explore.”
One of Osmond’s West Loop recommendations is called the Blind Barber, where you “enter through a barber shop and there’s a bar in the back.”
Osmond also says if you can’t make it before the end of the summer, there’s still lots happening in the fall.
“We have the Chicago Marathon (on) Canadian Thanksgiving and we have 40,000 runners that come from around the world,” she says. “In September we have a beach volleyball tournament that is volleyball professionals and it’s just really fun.”
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