Maximise your Avios, air miles and hotel points

Forums Other Destination advice Toronto to Chicago road trip

Toronto to Chicago road trip

  • spellman

    I’m doing a two week road trip in the summer from New York > Niagara falls > Toronto -> Chicago.

    I’ve done NY many times, so no questions there, but have some for the seasoned travellers to other cities:

    – Niagara Falls – can we do this in a day? Thinking of staying in Buffalo then driving up in the morning
    – How long to explore Toronto and Chicago as first time visitors (travelling with a teenager). I’m thinking two days/three nights in each.
    – Is it worth a stretch goal and trying to reach Montreal? (I have 14 days to play with)
    – Any routing suggestions between Toronto and Chicago? North or south of Lake Eerie? Detroit vs Cleveland? Must-see places to stop en-route?

    Appreciate any crowd-sourced wisdom and tips.




    Sorry – I can’t help with any of this but did you find a decent deal for car hire?!


    Buffalo – Niagara – Toronto is a couple of hours and you’d be able to see both sides of the falls. Having a gawk at the falls from both sides, a spin in the the Maid of the Mist to get wet under the falls, and a run around the various tat shops won’t take that long. Easily doable in a day.


    Niagara – an hour or a half day, wouldnt spend much more unless you really want to do the boat trip or behind the falls etc.

    Then depending what you and the teenager like there are amazing museums en-route.
    Rochester area – Strong Museum of Play, Jello museum if you like quirky
    Buffalo – Pierce Arrow museum
    Cleveland – Rock and Roll hall of fame
    Dearborn MI, The Henry Ford (1-2 days for this as there’s so much to see) and the Motown Museum

    if you’re heading down to the south of Lake Michigan then stop at Indiana Dunes for a couple of hours

    Then on to Chicago I could write a book… but there are many around. Look out for festivals while you’re there. Summer in Chicago is all about festivals, beach, and generally stuffing yourself. Spend at least 3 days, 4 if you can if it’s your 1st time. i’ve done NY a lot, but Chicago is special in a different way. It’s cleaner, brighter, friendlier and the buildings are more impressive.

    P.S. almost everything requires advance booking due to covid, almost all museums have timed entry tickets now and a lot sell out in advance so get your dates in order and book as soon as you can.


    IMHO (and having visited both) two days isn’t enough time for Torronto or Chicago. As a minimum I’d do 3 days in each. There are excellent mussums in both cities as well as plenty of walking and general sites to see.

    Your Teen if they are into sports might like to do a tour of the Skydome (baseball) and / or the Air Canada Centre (might be called something else these days) – Ice Hockey and Basket Ball arena. In Chicago it’s possible to tour both the baseball and football stadiums though I’ve only done the former. As a total non sports fan I do enjoy statium tours!

    Re Noagara Falls yes IMHO it’s a day trip destination to see the falls and gorge. The Canadian side is better than the US side. I’ve done both the maid of the mist boat ride and the behond the falls tours and enjoyed them both.

    Avoid the town though as it’s an actual tourist trap. If you wanted to spend the night then I’d go to Niagara on the Lake and then perhaps drive to Torronto the next day.

    Montreal is indeed also worth a visit but it may indeed be a stretch destinaion.


    Sports thoughts.
    Skydome 🙂 – it’s been the Rogers Centre for about 20 years. It’s a great place to see baseball, Toronto are in a division with the NY Yankees and the Boston Red Sox so a good chance of top opposition.
    Chicago. Has two baseball teams but I’d 100% recommend a visit to Wrigley Field to see the Cubs play. The stadium is one of the old style original parks, and oozes history. The area around Wrigley is littered with bars and food places, a game day experience there can’t be matched elsewhere.
    I loved Niagara, and the Cave of the Winds is a must-do, don’t wear much, you’ll get soaked.
    I’ll leave the other stuff, but if you or your son are sports fans a game at Wrigley is really special.


    We drove from NY to Milwaukee a few years back and had an amazing stay in a log cabin in Ohio, really great place to stay if location works? I won’t add link but it’s called Broken Arrow Cabin, Ohio.


    Sorry – I can’t help with any of this but did you find a decent deal for car hire?!

    I picked up a SUV from Thrifty for $1400 for 13 days (one-way rental from JFK to ORD). A lot more expensive that pre-Covid but manageable.

    The price was originally $1600 but Autoslash found a few cheaper rates over the past few months.

  • You must be logged in to reply to this topic.

The UK's biggest frequent flyer website uses cookies, which you can block via your browser settings. Continuing implies your consent to this policy. Our privacy policy is here.