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In December 2019, my family and I are flying from Winnipeg, MB Canada to West Palm Beach, Florida, through Chicago. On the flight down we have a 1.5 hour layover in Chicago. Scary but I think doable.

However on the way back it goes down to a 54 minute layover . Everyone I talk to says I’m in trouble. Are they right? I’m travelling with my husband, 2.5 year old with a car seat, and 2 pieces of checked luggage. Any advice what I should do?

I booked through Expedia and am wondering if I should phone them to cancel, change, or something. The flights were booked as round trip tickets all with the same confirmation number, operated by United.

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If your flights are on the same booking, your luggage will be transferred to your next flight so you don’t need to worry about that.

As your flight is with United airlines, all of those leave from terminal 1 so you don’t have to pass security to change terminal.

As you are travelling with a 2 1/2 year old with a car seat you should probably contact the airport to arrange some provisions regarding that matter.

Positive Passenger Bag Matching will prevent your flight leaving without your bags on it. After all, the connection is doable since it was sold together as a ticket but the child makes it tight.

Honestly, if you contact the airport it should be doable buts it’s your choice if you want to reschedule your flights.

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    Re: your first sentence (luggage transfer): I may be wrong as I've never done it myself, but from other answers on this site I was under the impression that passengers arriving in the US always have to collect their bags and take them through customs at the first US airport.
    – Chris H
    Commented Oct 14, 2019 at 7:29
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    @Daniil Shouldn’t the OP contact the airline, rather than the airport, for assistance with the transfer?
    – Traveller
    Commented Oct 14, 2019 at 8:01
  • Thanks for all the info and advice. It’s giving me a lot to think of.
    – DeeDee
    Commented Oct 14, 2019 at 12:58
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    @Daniil fwiw I now think your first sentence is actually correct after all, as the other answer points out OP is arriving from an airport with preclearance facilities. OP will essentially "arrive in the US" at the preclearance, immigration & customs procedures will happen there (before the flight) rather than when reaching the airport in the US.
    – Chris H
    Commented Oct 14, 2019 at 14:52
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Going south and entering the US, you will have to pass US Immigration. You'll do so at the US CBP Preclearance Facility at the Winnipeg airport, before you board your first flight. That makes the Winnipeg > Chicago flight effectively a "domestic" US flight. When you arrive at ORD, you'll just deplane and find your departure gate. You may have to pass security again, but United thinks you have enough time to do that, as their (United's) computer allowed the route on a single ticket. Because both flights are on United, your baggage will be checked-through directly from Winnipeg to Florida, and you won't see it in Chicago.

Coming back you have a shorter connection, but as above, United thinks there's enough time. And if you don't make the ORD > YWG flight, United's responsible to get you there and will put you on the next one. As above: because both northbound flights are on United, your baggage will be checked through and you won't see it until you arrive back in Winnipeg.

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  • Note that "the next flight" can sometimes be on the next day, and I would not rely on United to provide you with a hotel room overnight. If your flight is relatively late in the day, the OP should think about how much they're willing to risk having to reclaim their luggage, find a local hotel, get to the local hotel, wake up early the next morning, get back to O'Hare, and go through the whole process over again.
    – Michael Seifert
    Commented Oct 14, 2019 at 17:06

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