Need help choosing flights

[RedbirdFL]

I'm using FF miles to book tickets to NYC for our October cruise, but need your advice on which flights to choose:

 

Flight to NYC 2 days before our cruise (all flights leave our hometown at 9:10 am):

1) one with a 55 minute layover at IAD (Dulles) that lands at LGA (LaGuardia)

2) one with a 2 hour layover at IAD that lands at LGA

3) one with a 65 minute layover at IAD that lands at EWR (Newark)

 

(I like option 1, but is that cutting it too close?)

 

 

And for departure (both flights have same connection back to our hometown):

1) one that leaves at 1:00 pm from LGA and has a 3.5 hour layover at ORD (O'Hare)

2) one that leaves at 3:00 pm from LGA and has a 1.5 hour layover at ORD

 

(Is it easier to kill time in the ORD airport than in the LGA airport? I figure since we'll have our luggage with us after getting off the ship, then it's hard to do anything touristy in NYC for a couple of hours, is that right?)

 

Which options would you choose?

 

TIA for your help! :)

[ab0si]

I absolutely hate tight connections so for that reason alone, I would take the 2 hour connection.

 

ORD: you can get the world's best snack food there: Vienna Beef.

[RedbirdFL]

Thanks ab0si!

 

I forgot to mention that our cruise gets into NYC at 8 am if that makes any difference in choosing the flight home.

[paul929207]

I would go with option 2 going and option one on the way home.

[kenish]

Since you don't say which airport you're leaving/returning from and which airline(s) it's difficult to say. So my vote is for the longest connections listed. Provide the other important details and better recommendations could be made.

[Taxguy77]

Going home, #1.

Delays earlier in the day can make airports crowded later and timing more problematical.

[RedbirdFL]

Sorry I didn't provide all the info earlier.

 

The flights would be on United or United Express. We'd be coming from and going back home to Orlando.

 

The two flights on the way home leave from LGA.

[YXU AC*SE]

I assume you are a Mileage Plus member. You may also wish to check out ticketing on UA's Star Alliance partners, specifically US, via PHL. I looked at some 'dummy dates' for October and saw quite good availability for MCO LGA and you can redeem for as low as 25,000 points return in economy.

 

Enjoy your cruise!

 

Scott.

[RedbirdFL]

Thanks, all. I used my miles and booked itinerary #2 for arrival and #1 for departure.

 

Cruise is booked, hotel in NYC pre-cruise is booked, airline tickets booked - October 1 hurry up and get here!!