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From Chicago I like to take Porter to Toronto. You still get the MDW experience on this end, and then the destination airport "Billy Bishop" is right downtown (YTZ), the equivalent location would be like landing at Meigs Field so if your destination is downtown Toronto, you are already there - literally walk to some of the hotels, after taking a 2 minute ferry ride across the ditch.
I don't know where your starting point was, but you should consider flying to a Porter airport on Southwest (Chicago MDW, Pittsburgh, Dulles, Newark, Boston) and then transferring airlines to check the price point against renting a car and driving.
I've only been to MDW, Dulles, and BOS, so I can't recommend the layover experience at Pittsburgh or Newark. MDW has plenty to eat though and is pretty close to Toronto.
Caveat: Porter flies only Bombardier Q400 turboprop - the ride isn't quite as smooth as Southwest's 737's if you hit choppy air. I would recommend you take Southwest as close as possible to minimize this potential issue. Other than that, Porter is great though. Customer service wise they are the "Southwest of Canada" in my opinion and their terminal at Billy Bishop airport is by far the best free lounge I've been at for a layover. Snacks and Canadian wine are included. They run sales all of the time, in fact $105 per person one-way today from MDW:
https://www.flyporter.com/en-us/special-offers/website-savings
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@DancingDavidE thanks for the feedback! Great luck....I'm actually based in Chicago. Looked into Porter and sure enough their flight prices are very reasonable.
Next I'll look into the ferry 🙂
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Another vote for Porter. Great service, and direct to downtown, avoiding YYZ. Also, you don't need to take the (very short) ferry ride anymore. They've built a tunnel to the airport, and it's a short walk.