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  1. #1

    Default New York to Chicago road trip advice

    Hello everyone! First post here (I posted a similar question on Reddit but I thought this forum would fit better).

    I'm thinking about visiting the USA for the first time in the summer of 2022 or 2023. I will travel with my brother and my mother, who is not very old but tends to get tired easily. I haven't laid out a full plan yet, I'm just wondering about whether the ideas I have floated around so far are feasible.

    We'd like to visit New York and then go to Chicago to meet some friends who live there.
    I plan on doing something like this:

    - Fly to NY and spend 3 full days there (this means 4 or 5 days including jet lag adjustment, transfer from the airport and car rental upon leaving)

    - Road trip: 2 or 3 days. I thought about seeing Niagara Falls but I'm not sure about timing and visas required to cross the Canadian border. Is there anything else worth seeing along the way? I guess you'd need to get to Niagara Falls during the day to enjoy it fully, so we'd better allot 3 days for the trip, but I feel like one day is going to be wasted if we cannot really see anything else.

    - Chicago: 3 days including arrival (ideally, arriving before noon on the first day and immediately giving back the rental car since we would use public transport). Then we'd fly back home from Chicago.

    Do you think this is feasible? What would you suggest to see along the way? Would a normal sedan be enough for 3 people and luggage? Thank you in advance~

  2. #2
    Join Date
    Mar 2005
    Tucson, AZ

    Default Farther Along

    Welcome aboard the RoadTrip America Forums!

    Actually, for all your questions, you are father along in your planning than most of our first time posters. You've got a basic plan; your time allotted seems quite reasonable; a 'normal sedan' should easily accommodate three people with normal airplane luggage; and your major 'attractions' (including your visits to New York and Chicago) are set. So... Let's start with the bad news:

    Currently, travel between the United States and Canada is pretty restricted, and air travel passengers are now are required to show a recent negative covid test. So when you make this trip matters a lot. I don't expect things to get much better until summer myself. You'll just have to wait and see.

    But mostly, if you get here, you should be fine. Most travel services such as lodging and restaurants are operating, even if at limited capacity. Just be sure to plan and book your overnight stays before your departure and be ready on occasion to eat drive-through take-out. As for the only attraction you list, Niagara Falls, and assuming border crossings will still be problematic, what I would recommend is that you look at one of the boat tours of the falls out of the US side. There are at least four such, but two of them are currently (and hopefully temporarily) closed.They do give a unique experience.

    Beyond that we'd need to know a bit more about your interests and limitations. There are certainly plenty of things to see and do between New York and Chicago including scenic, historic, quirky, and leg-stretching attractions. Also, what is your preferred driving experience? Back roads? Major surface highways? Interstates/Motorways/Autobahns/Autostrade/etc? Which brings up another, possibly relevant question: where are you coming from?


  3. #3
    Join Date
    May 2003
    Green County, Wisconsin


    Welcome to the RTA Forum!

    The plan you've started with is certainly feasible and you've already got the foundation for a good trip.

    There is certainly plenty to see between NYC and Chicago - it just depends upon your interests - and really there never should be a "wasted" day on the road unless you get it in your mind that there is nothing worth seeing. The question is what kinds of things would you like to see. Nature, History, Cities, Oddities? The difference between taking 2 and 3 days is also fairly significant - with 2 days, you wouldn't have time to see much beyond Niagara Falls, while 3 days opens up a ton of other options. (Also beware that redditors frequently offer some frankly reckless opinions about how much ground is reasonable to cover in a day. )

    As far as logistics, going through Canada could certainly make sense - both to see the falls and to cut across Ontario to Detroit. Without knowing where you're coming from, we can't say what visa issues you might be looking at, but if you're traveling to the US on the Visa Waiver Program, you shouldn't have any issues on the US part as long as you're total time in North America is less than 90 days (This is also presuming the Covid restrictions of today are gone by 2022/23). One other thing you will want to check, however, is with the rental car company to make sure you can take it into Canada. Many will say unlimited mileage, but only within the US.

    Speaking of rental cars, yes, a normal sedan will work just fine. I would recommend looking to do a full sized sedan, which is going to give you the most comfort and probably the most additional features, without the exorbitant price premiums that are usually charged for SUVs. For one way rentals you usually have to start/end at airports so I would recommend trying to rent from Newark. Renting in New Jersey is often (but not always) cheaper than New York, but at the very least it will say you considerable time and tolls of having to drive across the city/out of Queens if you rent from LaGuardia or JFK. Similarly, in Chicago returning to Midway instead of OHare would save you from driving all the way across Chicago to return the car. You could also even look at returning to South Bend, Indiana - as there is a commuter train that will take you right from South Bend's airport into Downtown Chicago.

  4. #4


    Hello AZBuck and Midwest Michael, thank you for your answers!

    I'm from Northern Italy and my driving experience is about 80% driving a small car among narrow country roads and medieval villages and 20% driving in big cities and 2 or 3-lane "highways" (I heard Autostrade are quite different from Interstates in the US).

    My trip is going to happen whenever covid won't be dangerous like today, at best when we are vaccinated and at worst when we can travel without having to show a negative test or something similar. I think it would be irresponsible of me to travel to another continent and potentially carry virus mutations with me just for the sake of tourism.

    As for what are our interests, we are three people with very different ideas of what we'd like to have from this trip, but my mother is definitely going to be prioritized, since this could be her "once in a lifetime" travel to America.

    My mother's interests: she enjoys fine art and landscapes. I believe she wants to be genuinely amazed by this trip (not as in amusement-park-amazed: she wants her experiences to be as genuine and un-artificial as possible). She wants to get a grasp of the American culture and lifestyle, in the cities, the suburbs, the countryside alike.
    As I said, she gets tired pretty easily, so she wouldn't like a trip as dense as my ideal (to make a comparison, when I went to Rome on my own I'd walk 10 miles everyday and see 3 to 5 attractions daily; when she came with me we'd walk about 4 miles and only see 2 attractions, waking up later and taking our time to have lunch and dinner properly).
    She's much more active in the afternoon/evening, but I guess jet lag could make her a morning person hehe.

    My interests: art, music, history and cultures, mostly. I think I'll get my fair share of museums in NY, but ideally I would like to stop by and listen to some live r&b (the Blues Brothers Band kind of music). I'd also love to learn more about the culture of Native Americans or Amish people, but I don't want to be perceived as a freak-show-goer, so the visit should be the as respectful as possible (maybe some place with museums or other educational landmarks?).

    My brother's interests: he too likes music and would thoroughly enjoy some American r&b, but his true passion is cars and motors. I'm fairly sure there's much to see in Detroit and Indianapolis but I don't know how enjoyable for him (he sure enjoys seeing cars and trucks running, but he's also into the engineering part of it). He's pretty much into the idea of the road trip itself but unfortunately he'll be under 25 by then so no driving for him!

  5. #5
    Join Date
    Mar 2005
    Tucson, AZ

    Default OK, Then

    None of the roads you'll see on this trip come close to the kinds of roads you've described around your hometown. (I've driven both.) Indeed, there's only one part of your trip that's even 'hilly', and that's getting from New York to Niagara Falls, but even those hills can be avoided.

    For shorter walks, I'd recommend that you use the various state park systems along your route, once you've decided on a route. Those who would like more exercise can do so in the evening during the summer months as dusk typically doesn't start falling until 8:00 or later.

    I'm afraid that the largest group of Amish communities is in southeastern Pennsylvania and not reachable in the timeframe of this trip.

    Some Specific Suggestions:
    First, the National Museum of the American Indian is in New York City. The Erie Canal in northern New York is both historic and is now basically a long linear park. There are also several other art/historic sites along the canal and US-20 which runs parallel to it. Seneca Falls is the Birthplace of the Women's Movement. You should also take a look at what's available at the Rochester College of Art and Design when you'll be in the area.

    Hitting multiple interests is Ford's Greenfield Village. A 'detour' to the Indianapolis Motor Speedway would chew up an entire day. Indiana Dunes National Park is often overlooked by travelers who just want to 'get there', but it's definitely worth considering. Your best bet for Rhythm and Blues is, as I suspect you know, Chicago.

    Last edited by AZBuck; 01-31-2021 at 09:04 PM.

  6. #6


    Going to the Native American interest, there are a couple possible options.

    The Iroquois have a museum in a town called Howes Cave (better known for the namesake caverns), which is a bit off the routing AZ Buck described using US 20, but could be worked in.

    The Oneida nation also has a cultural center (along with the better known casino) in the town of Oneida, which is not far North of US 20.

    (FYI - US 20, I-90 and NY 5 basically parallel each other across the state, sometimes farther apart, sometimes as close as two of them sharing a roadway).

    In terms of the Amish thought, as noted the most well known ones are in PA, but NY actually has a fair number of settlements. Not too certain that any have museums or similar, but there seems to be a fairly large cluster in the southwestern corner of the state, which may be feasible after leaving Niagara Falls if you stay within the US and follow the 5/20/90 cluster towards Pennsylvania to continue westward. It also mentions that some of these migrated from Ohio, so there may be more there to look at.

  7. #7
    Join Date
    May 2003
    Green County, Wisconsin


    A couple more places that would fit your interests.

    The Rock and Roll Hall of Fame in Cleveland really is a good stop, and you'll find plenty of R&B are part of Rock's history.

    There is also a Motown Museum in Detroit, although I've never been.

    For the interest in cars, a smaller less known stop would be the Studebaker Museum in South Bend. It really goes through the entire development from a horse buggy company into automaking, so plenty of engineering to appreciate.

    If your mom is into fine art, then The Art Institute of Chicago should be a must stop - some have even called it the best art museum in the world. It's also surrounded by Millennium and Grant Parks, which are great open spaces with their own sets of public art like the bean. And for the added roadtrip bonus, the Art Museum's front door is essentially the starting point of History Route 66 - you'll see the sign if you look across the street!

  8. #8
    Join Date
    Mar 2005
    Western/Central Massachusetts

    Default Indiana Automotive

    While Detroit is considered the motor city and the heart of the American automotive industry, Indiana has quite a bit of history in this regard and there are still places to appreciate that. Here's some suggestions that may or may not work given they are not on the direct route, but aren't a huge detour, either.

    Midwest Michael pointed out the Studebaker Museum - I've not been but have heard it is very good. You might also consider the Auburn-Cord-Duesenberg museum, housed in the Auburn factory showroom building. In the same parking lot is the National Automotive & Truck Museum. I've been to both the ACD and the Natmus and found them both very enjoyable, with the ACD building architecture being as much a part of the experience as the items contained within.

    If you're interested in seeing autos being built, you can take the Subaru factory tour. I managed to get on this tour a few years ago and it was quite impressive.

  9. #9
    Join Date
    Nov 2005
    The Great Midwest, Illinois to be precise


    If you drive by Toledo, Ohio, have a Hungarian hot dog at Tony Packo's. There are several of them, but go to the original one on Front Street.

    Plus, if you go by Indianapolis, don't miss stopping at the Indianapolis Speedway and tour the museum and take the bus trip around the track.

  10. #10
    Join Date
    Jan 1998
    Las Vegas, Nevada

    Default Welcome back RoadDog!

    Wow, this is so cool -- I haven't seen any posts from the RoadDog for months! Welcome back.


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