Destination Showdown: Chicago vs. Toronto

It's the US vs. Canada as Chicago and Toronto battle it out for the title of Best Lakeside City. You be the judge!

It's the US vs. Canada as Chicago and Toronto battle it out for the title of Best Lakeside City. You be the judge!

Round 1: Where to Eat Round 1: Where to Eat
Lou Malnati’s Pizzeria
439 North Wells St, Chicago, IL
Lou Malnati’s has been serving some of the best deep-dish pizza in the city for more than 30 years.
Paddington’s Pump
95 Front St East Market Square, Toronto, ON, Canada
Home to the peameal bacon sandwich, Paddington’s is the place to get authentic Ontario cuisine.
David Burke’s Primehouse
616 North Rush St, Chicago, IL
Chicago is a meat town, and when you want to indulge in some prime steak, David Burke’s is the only place to go. Serving the highest-quality beef around, Primehouse is the place to get a premium cut.
Marben Restaurant
488 Wellington St West, ON, Canada
Marben’s is a classy establishment that offers some of the best cuisine in all of Canada. Be sure to try their burger!
The Wiener’s Circle
2622 North Clark St, Chicago, IL
There is no better place to get a Chicago dog than the Wiener Circle, a late-night hub.
Restaurant 360
301 Front St West, Toronto, ON, Canada
Get some thrill with your meal at Restaurant 360, located at the top of the CN Tower, and sample fine wine as you look out over the Toronto cityscape.
Round 2: Where to Sleep Round 2: Where to Sleep
James Hotel
44 East Ontario St, Chicago, IL
Located in the heart of the city, the James Hotel offers luxurious rooms. This boutique hotel is as posh as it gets – you’ll feel like Chicago royalty.
Gladstone Hotel
1214 Queen St West Toronto, ON, Canada
A boutique hotel that embodies Toronto’s art scene, the Gladstone Hotel is the perfect place for budget travelers visiting Ontario.
The Wit Hotel
201 North State St, Chicago, IL
The Wit Hotel offers a modern take on a classic city. With hip rooms and an awesome rooftop bar, this is the place to be seen in Chicago.
Trump Tower Toronto
325 Bay St, Toronto, ON, Canada
The Donald does it again … only this time in Canada. Trump Tower Toronto offers some of the most decadent hotel rooms in the country, but it will cost you a pretty penny.
Round 3: What to Do Round 3: What to Do
Willis Tower Skydeck
233 South Wacker Dr, Chicago, IL
The tallest building in North America, the Willis Tower offers visitors breathtaking views of the city from the Skydeck.
CN Tower EdgeWalk
301 Front St West, Toronto, ON, Canada
Get your adrenaline pumping at CN Tower’s EdgeWalk, where you can walk around the roof of North America’s tallest freestanding structure ... outside.
Millennium Park
201 East Randolph, Chicago, IL
Home to the famous Chicago Bean, Millennium Park is the perfect summertime hangout spot. 
Castle Loma
1 Austin Ter Toronto, ON, Canada
This Canadian castle is a beautiful demonstration of Western architecture.
Navy Pier
600 East Grand Ave, Chicago, IL
Go for a ride on the city’s largest Ferris wheel on Navy Pier.
Canada’s Wonderland
9580 Jane St, Vaughan, ON, Canada
Home to Canada’s tallest and fastest rollercoaster, Canada’s Wonderland is a great place for thrill seekers.
Shedd Aquarium
1200 South Lake Shore Dr, Chicago, IL
Explore the depths of the oceans at Chicago’s Shedd Aquarium, home to thousands of aquatic species.
Canada Beach
1 Bonfield Ave, Toronto, ON, Canada
Located right on Lake Ontario, Toronto’s beaches are a great escape for city-dwellers.
Wrigley Field
1060 West Addison St, Chicago, IL
Home to the Chicago Cubs, Wrigley Field is the nation’s second-oldest ballpark.
Royal Ontario Museums
100 Queens Park Toronto, ON, Canada
One of the largest museums in Canada, the Royal Ontario Museum has a vast collection of rare dinosaur fossils.
Second City
1616 North Wells St, Chicago, IL
A sketch-comedy mecca, Second City was the starting place of dozens of famous comedians, from John Candy to Tiny Fey.
Niagara Falls
6650 Niagara Parkway, Niagara Falls, ON, Canada
Only an hour’s drive from downtown Toronto, Niagara Falls is one of the great natural beauties in North America.
308 West Erie St, Chicago, IL
Located in Chicago’s River North area, Cuvee is one of the top nightclubs in the city.
Maison Mercer
15 Mercer St, Toronto, ON, Canada
Step into Maison Mercer, a popular Toronto nightclub, and you’ll feel like you’re in Europe.
O’Callaghan’s Irish Pub
29 West Hubbard St, Chicago, IL
A true Irish pub, this is a place where Chicagoans get their drink on.
The Ballroom
145 John St Toronto, ON, Canada
Looking for a nightspot that’s a bit less clubby? The Ballroom couples drinking with bowling – a perfect combination!

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